United States Court of Appeals For the First Circuit
Nos. 11-1660, 11-1742
UNITED STATES OF AMERICA,
RAQUEL DELGADO-MARRERO, ÁNGEL L. RIVERA-CLAUDIO,
APPEALS FROM THE UNITED STATES DISTRICT COURT FOR THE DISTRICT OF PUERTO RICO
[Hon. José Antonio Fusté, U.S. District Judge]
Torruella, Howard and Thompson, Circuit Judges.
Rafael F. Castro-Lang, for appellant Delgado. Linda Backiel, for appellant Rivera. Jacqueline D. Novas-Debién, Assistant United States Attorney, with whom Rosa Emilia Rodríguez-Vélez, United States Attorney, Nelson Pérez-Sosa, Assistant United States Attorney, Chief, Appellate Division, and Luke Cass, Assistant United States Attorney, were on brief for appellee.
February 11, 2014
TORRUELLA, Circuit Judge. Former San Juan Municipal
Police Officers Raquel Delgado-Marrero ("Delgado") and Ángel
Rivera-Claudio ("Rivera") were convicted by a jury on drug and gun
charges arising from an FBI reverse sting operation called
"Operation Guard Shack." They each received a fifteen-year
sentence. On appeal, Delgado and Rivera raise multiple challenges,
claiming both trial and sentencing errors by the district court.
They each seek either a new trial or resentencing.
Our discussion begins with Delgado's contention that the
district court committed reversible error by excluding the
testimony of a defense witness. Because we agree with Delgado that
the district court erred on this front, and that a new trial is
needed to mend the error, we do not address any of her other
With respect to Rivera, we agree that his sentence cannot
withstand the Supreme Court's decision in Alleyne v. United States,
133 S. Ct. 2151 (2013). Applying Alleyne retroactively, we find
that the district court plainly erred in articulating the jury
instructions imparted in connection with a post-verdict special
jury form. We further find that Rivera's other claims of error
The necessary details follow, with a recitation of "the
facts in the light most favorable to the government." United
States v. Flores-Rivera, 56 F.3d 319 , 322 (1st Cir. 1995).
A. Operation Guard Shack
The FBI launched "Operation Guard Shack" as part of its
efforts to combat police corruption throughout Puerto Rico.1 As
relevant here, the FBI hired a Puerto Rico Police officer ("Officer
I") to pose undercover as a corrupt policeman with close ties to a
mid-to-high-level local drug dealer.2 Officer I's main
responsibility was to recruit fellow police officers willing to
provide armed security during a staged "multi-kilo" drug
transaction. The FBI also hired another undercover Puerto Rico
Police officer, "Officer II," to play the role of the dealer during
the staged drug transaction.
Delgado and Rivera were working partners stationed at the
Antillas Police Precinct in San Juan, Puerto Rico. Delgado, a
1 According to an official press release issued by the United States Justice Department, Operation Guard Shack was "the largest police corruption investigation in the history of the FBI," and involved "125 undercover drug transactions conducted . . . in several locations in Puerto Rico, from July 2008 until September 2010." The operation yielded 26 indictments against 89 law enforcement officers and 44 other civilians. 2 To protect their identities, we omit all references to the names of the undercover agents involved in the case. For his participation in Operation Guard Shack, Officer I received $1,400 monthly, but his contract with the FBI was subject to a six-month review and could be terminated at will. Officer I was also provided with "expensive" cars in order to portray the image of a corrupt officer who had money to spend. At the time Officer I contracted with the FBI, his entire salary from the Puerto Rico Police Department was being garnished on account of a child support debt.
divorced mother of two, had no prior criminal record. She began
her career as a municipal police officer in her late twenties.
Before her arrest in 2010, Delgado had enjoyed five years of
experience on the force, had never been the subject of an
administrative complaint, and had received the award of "Municipal
Police Woman of 2009." For his part, Rivera, who was twenty-four
years old at the time of his arrest, enjoyed four years of
experience in the municipal police force and, like Delgado, had
untarnished criminal and administrative records.
Officer I reached out to Delgado sometime in the middle
of 2009 as part of his undercover role as a corrupt policeman.
Officer I knew Delgado from childhood. They grew up near each
other, were middle-school classmates, and had once shared a close-
knit circle of friends. After middle school, however, Officer I
and Delgado went their separate ways and eventually lost touch with
More than a decade later, Officer I identified Delgado as
a possible target of Operation Guard Shack during a conversation
with her ex-husband, who had asked to meet with him for an
unrelated personal matter.3 During the meeting, when Officer I
asked about Delgado, her ex-husband told him that they were no
3 Delgado's ex-husband was also a municipal police officer whom Officer I knew from childhood. He met with Officer I to discuss drug-related problems in his neighborhood and to ask if more patrolling could be provided. The ex-husband's current spouse was present during the meeting.
longer together and that Delgado had several part-time jobs
providing nighttime door security at veterinarian clinics as well
as some pubs. Delgado's ex-husband also shared with Officer I his
distaste for Delgado's part-time jobs, stating that he was
concerned that the jobs were in unsafe locations. According to his
testimony at trial, Officer I understood the ex-husband's concerns
to mean that Delgado was part-timing in places where drug-
trafficking activities occurred.
Officer I asked for Delgado's phone number during a
second meeting with her ex-husband. Soon thereafter, he called her
to see whether she was in fact doing part-time jobs at questionable
locations. Although the FBI had instructed that phone
conversations with Operation Guard Shack targets be recorded,4
Officer I testified at trial that he was unable to record the first
call with Delgado because he made it while on duty, with fellow
officers nearby. Another unrecorded phone call took place shortly
thereafter; Officer I testified that he could not record that
conversation because some of his family members were nearby when he
placed the call.
Officer I recorded a phone conversation with Delgado for
the first time on July 20, 2009. The transcript of that
conversation reflects that Officer I had previously invited
4 The FBI provided Officer I with special recording equipment for this purpose.
Delgado, and she had agreed, to participate in a drug transaction,
in which Delgado and an unnamed fellow officer5 would provide
security in exchange for $2,000 each.6
Officer I recorded a second call with Delgado on July 23,
2009. This time, as depicted in the call's transcript, Officer I
explained to Delgado that the transaction would take place inside
a house; that Delgado and the fellow officer's job was simply to
frisk two people that would come to pick up the "kilos"; that the
job would begin at 8:00 p.m. and would last thirty minutes to an
hour; and that Officer I would personally direct Delgado on how to
get to the house.
B. The Sham Transaction
The sham drug transaction took place the next day. With
the assistance of Officer I, who provided final minute-by-minute
directions by phone, Delgado and Rivera arrived at the apartment in
the municipality of Dorado, Puerto Rico, where the "transaction"
was to take place. Officer I and Officer II waited in the
apartment, where the FBI had placed hidden cameras and microphones
in order to record the events.7 Also in the apartment was a duffle
5 The fellow officer turned out to be Rivera, whom Delgado convinced to accompany her during the transaction. 6 Neither the word "drug" nor any specific type of drug was mentioned during the conversation, but Delgado testified at trial that she assumed the transaction involved drugs. 7 A crew of FBI agents controlled the hidden equipment and monitored the events from an apartment next door.
bag containing the purported drugs underlying the sham transaction
-- seven packages, or "bricks," that the FBI had prepared to
resemble one-kilogram blocks of actual cocaine.
The video recording of the "transaction" begins when
Delgado and Rivera step into the apartment. Officer I, Delgado,
and Rivera enter in full view of a hidden camera that was recording
the entry door and foyer area of the apartment. To the left of the
entry door is a kitchen, and Officer I offers drinks to Delgado and
Rivera. Delgado takes a soda and Rivera a beer. Officer I then
ushers them into a living room, where Officer II, in his role as a
drug dealer, sits in the middle of a large L-shaped sectional sofa.
Another hidden camera captures the moment when Officer I,
Delgado, and Rivera come into the living room. Officer I and
Rivera sit on the sofa where Officer II awaits seated. Delgado
asks where the bathroom is and steps out of the camera's range.
While Delgado is in the bathroom, Officer I and Officer
II engage Rivera in friendly banter. Among other things, they ask
Rivera about the type of gun given to the municipal police. Rivera
states that he dislikes the old, secondhand gun he was provided,
and, upon further probing from Officer I, retrieves the gun from
underneath his jacket, waves it in the air so that the others can
see it, and tucks it back in. Officer I and Officer II also show
Rivera the gun each is carrying. When Delgado returns from the
bathroom, the gun-related discussion continues, and she also shows
her official gun, which she was carrying inside her waistband,
hidden underneath her shirt. Delgado then sits down on the sofa
between Rivera and Officer II.
The friendly banter continues for half an hour, including
remarks about Delgado's birthday party, which is happening later
that night. The conversation is interrupted when the purported
drug buyer knocks at the door.8 Immediately, Officer II instructs
Rivera to open the door and to make sure that nobody enters the
apartment armed. Rivera picks up a set of keys from the coffee
table in front of the sofa and leaves to open the door. Officer I
gets up and signals Delgado to follow him in order to assist
Rivera. She gets up and follows Officer I out of the living room.
The hidden camera recording the area of the entry door
captures Rivera approaching. He opens the door and orders the
purported drug buyer to stand still and proceeds to frisk him.9
Finding no weapons on the newcomer, Rivera walks him to the living
room. There, the purported buyer greets Officer II and sits down
on the sofa, and Officer I and Rivera return to their seats.
Delgado remains standing and goes in and out of the camera's frame,
8 Another undercover agent ("Officer III") plays the part of the buyer. 9 Although not seen on the video footage provided to us, another hidden camera apparently captured Officer I and Delgado in the hallway watching Rivera frisking the purported drug buyer. Officer I's trial testimony corroborated that they were in the hallway watching Rivera.
but her voice can sometimes be heard as she participates in the
The friendly banter continues exactly where it left off.
It is interrupted approximately fifteen minutes later, when the
purported buyer tells Officer II to bring him the "stuff" because
he is leaving. Officer II then casually tells Rivera to call an
elevator that is apparently nearby, while at the same time
signaling to him the direction of the elevator he is referring to.
Rivera gets up from the sofa and walks away from the hidden
camera's view. Officer II then tells Rivera, who is still out of
view but apparently in the living room, to wait for the elevator
doors to open and to hand what is inside the elevator to the buyer.
A few seconds later, Rivera comes back carrying a duffle bag. He
hands it to the buyer, and sits down on the sofa next to him.
Though the coffee table in front of the sofa blocks the
camera's view, it appears that the purported buyer places the bag
on the floor, between his legs, and opens it. He takes two
packages out of the bag and stacks them on top of the coffee table.
He does the same with two additional packages. He next seems to
fiddle with something in the bag. Rivera remains seated to the
right of the buyer. Delgado is still standing and does not appear
in the video at this moment. One of Delgado's hands, which holds
a cellular phone, comes into the camera's frame briefly a few
times. Her voice can also be heard during the conversation, so it
is safe to conclude that she remains somewhere in the living room.
The jovial atmosphere continues. Approximately a minute
after placing the four packages on the coffee table, the purported
buyer places them back into the duffle bag, closes it, stands up,
places the carrying strap of the bag on his left shoulder, shakes
hands with everyone, and walks to the entry door escorted by
Rivera. Delgado stays in the living room chatting with Officer I
and Officer II. When Rivera returns, Delgado goes to the bathroom
a second time.
A new round of banter begins with Rivera, Officer I, and
Officer II sitting around the sofa. Delgado joins in when she
returns from the bathroom, though her attention often centers on
her cellular phone, as she appears to be exchanging text messages
with someone. A few minutes into the conversation, Officer II
instructs Officer I to go get the "guys' stuff." Officer I walks
out of the living room, away from the hidden camera's view. He
appears back in the video a minute later holding two beers in his
left hand and a stack of money in his right. He places the two
beers on the coffee table in front of Rivera and Delgado, then sits
down on the sofa to the left of Officer II. Between jokes and
laughter, Officer I counts the money, eventually handing $1,000 in
$20 bills to Rivera. Rivera counts the money given to him.
Officer I and Rivera follow the same routine until $4,000 in cash
exchanges hands. Upon Officer II's inquiry, Delgado and Rivera
state that they are available to do a second job later on.
They are still on the sofa, jovially chatting with
Officer I and Officer II, when the video recording from the camera
in the living room cuts off. The video recording from the hidden
camera in the entry area cuts off around the same time. One hour
and a few minutes have lapsed since Delgado and Rivera stepped into
C. The Arrest and Trial
The FBI arrested Delgado and Rivera on October 6, 2010,
pursuant to a four-count indictment. Count One alleged that
Delgado and Rivera knowingly and intentionally conspired to possess
with intent to distribute five kilograms or more of a substance
containing a detectable amount of cocaine, in violation of 21
U.S.C. §§ 841 and 846. Count Two charged that Delgado and Rivera
aided and abetted each other in an attempt to possess with intent
to distribute five kilograms or more of a substance containing a
detectable amount of cocaine, in violation of §§ 841 and 846, and
18 U.S.C. § 2. Counts Three and Four alleged that Delgado and
Rivera, respectively, knowingly possessed a firearm in furtherance
of the drug trafficking crimes charged in Counts One and Two, in
violation of 18 U.S.C. § 924(c)(1)(A).
At trial, the government presented three witnesses:
Officer I, Officer II, and the FBI special agent (the "Special
Agent") who prepared the apartment and the duffle bag for the
transaction. It also introduced into evidence (1) the two recorded
phone calls between Officer I and Delgado; (2) the video recording
of the transaction; and (3) five pictures of the duffle bag
containing the "bricks" before the FBI placed it in the Dorado
apartment. The government's theory was that the video recording of
the transaction spoke for itself and showed guilt beyond reasonable
doubt on all counts.
In her defense, Delgado argued entrapment. She presented
her own testimony and the testimony of her ex-husband. In support
of her entrapment defense, Delgado testified that for approximately
one month, she rejected Officer I's persistent invitations of part-
time employment; that during this period, Officer I called her
repeatedly and sometimes took her out on dates; that she had
romantic, sexual affairs with Officer I in 2005 and 2009; that
weeks after the transaction, Officer I took her out on a date
during which they had sexual intercourse; and that Officer I preyed
on their long-lasting friendship and trust to overcome her
expressed and firm resistence to participate in the transaction.
Despite this reluctance, Delgado testified that she
finally gave into Officer I's insistent pressure. She further
explained that she contacted her partner, Rivera, and that they
"decided to go to the place" where the part-time job organized by
Officer I was to be held. She stated that, following directions
from Officer I, she asked for $2,000 each -- for herself and Rivera
-- in exchange for their roles in the deal; that Rivera drove her
to the apartment depicted in the video; and that the two partners
entered the apartment together with Officer I. She admitted that
she was aware that the "bricks" involved in the transaction were
narcotics and that she was doing something wrong, but she
maintained that she only participated in the transaction because of
Officer I's insistence, because of the "sentimental or romantic
relationship" she had with him, and because of her trust in him.
In further support of her entrapment defense, Delgado
sought to present the testimony of Brenda Rosa-Valentín ("Rosa-
Valentín"), the younger sister of a fellow policeman Officer I grew
up with and considered a dear friend. But on an objection by the
government, the court decided to hear her testimony outside the
presence of the jury, and ultimately ruled it inadmissable
extrinsic evidence under Fed. R. Evid. 608(b).
Rivera neither took the stand nor presented any witnesses
in his defense.10 During opening statements,11 Rivera's counsel told
the jury that he intended to show that Rivera "was not guilty of
conspiracy as charged in the Indictment," and that Rivera had no
intention of participating in the transaction before Officer I
10 Rivera and Delgado each had their own counsel. 11 The defendants' opening statements were deferred until the beginning of their case-in-chief.
lured Delgado into it. Although the record shows that counsel told
the court that he intended to present a derivative entrapment
defense, the court ultimately did not allow the defense.12
After a three-day trial, the jury found Delgado and
Rivera guilty on all counts. They were each sentenced to
concurrent terms of ten years on Counts One and Two, corresponding
to the statutory minimum under 21 U.S.C. § 841(b)(1)(A) for
possession with intent to distribute five kilograms or more of
cocaine. On Counts Three and Four, respectively, Delgado and
Rivera each received a five-year sentence for possession of a
firearm in relation to a drug trafficking crime, to run
consecutively with their ten-year sentences under Counts One and
Two, for total terms of imprisonment of fifteen years each. This
consolidated appeal timely ensued.
A. Delgado's Evidentiary Challenge
As relevant here, Delgado argues that the district court
committed reversible error in excluding Rosa-Valentín's testimony,
which "prevented [her] from presenting important evidence that
12 For a discussion of the derivative entrapment defense, see United States v. Washington, 106 F.3d 983 , 992-96 (D.C. Cir. 1997) (cited by United States v. Luisi, 482 F.3d 43 , 52-58 (1st Cir. 2007) (discussing third-party entrapment, and distinguishing derivative entrapment from vicarious entrapment)). On appeal, Rivera does not challenge the district court's determination that the derivative entrapment defense was unavailable to him. In his appellate brief, Rivera states that his "only defense" at trial was the "right to the presumption of innocence."
[would have] aided . . . in establishing her only defense, that she
was entrapped by [Officer I] in participating in the offense
conduct." We agree.
When the defense examined Officer I, the government
objected, on relevancy grounds, to a question regarding his
recollection of prior interactions with Rosa-Valentín. At sidebar,
Delgado's counsel proffered that Rosa-Valentín, who was one of
Delgado's witnesses, would testify that Officer I had offered her
money in exchange for providing contact information of policemen to
entrap. Rosa-Valentín would also testify that Officer I had
confessed to her his desire to kill a man he thought had wronged
her brother.13 Following the proffer, the court stated: "Well, I
will not allow you to ask [about] that unless I first hear that
from [Rosa-Valentín]. . . . Because I think this is too much of a
stretch. If you give me . . . some foundation evidence that he has
done that, I will allow you to [recall Officer I]."
When the interrogation resumed, Officer I admitted that
he had offered money to Rosa-Valentín in exchange for police
officers' names. When asked about the timing of his proposal,
Officer I said that he first mentioned it to Rosa-Valentín
indirectly during a chance encounter with her while on duty
13 Apparently, the wife of Rosa-Valentín's brother committed suicide in the middle of an extramarital affair with the man whom Officer I allegedly said that he wanted to kill.
patrolling his sector. In this regard, Officer I testified that,
in responding to a late-night complaint about noise and loud music,
he arrived at a commercial establishment where a birthday party
appeared to be taking place. The party turned out to be Rosa-
Valentín's. As Officer I recounted: "[W]hen the person that came
out to explain why the music was so loud turned out to be her, I
greeted everybody and then I continued patrolling. I explained to
her that they needed to lower the music down, and . . . they told
me that they were just about to close." Officer I denied having
any beers or allowing the party to continue after 2:00 a.m. in
contravention of a municipal ordinance. He also denied going to
Rosa-Valentín's house looking for her more than fifteen times after
the birthday party.
As proffered, Delgado called Rosa-Valentín to the witness
stand as part of her case-in-chief. The government immediately
objected, arguing that the testimony was irrelevant. At sidebar,
defense counsel repeated the proffer previously given about Rosa-
Valentín's testimony, and the court stated that it would have "to
hear the evidence outside of the presence of the jury . . . to see
if it's relevant."
Outside the presence of the jury, Rosa-Valentín stated
that Officer I was her brother's lifelong friend and that she had
known him for approximately thirty-three to thirty-four years.14
She also stated that, during the funeral services for her sister-
in-law, Officer I told her twice that he wanted to kill the man
involved in the extramarital affair that allegedly caused the
Rosa-Valentín further testified that Officer I "used to
tell [her] when he came home all the things that he used to do."
Specifically, she testified that Officer I mentioned to her that he
would go to a drug point in his patrolling sector, arrest a seller,
"and [he] would tell the guy to call his boss. . . . [W]henever
they got in touch with the drug dealer, [he] would tell him that in
order to release his runner, he was going to have to give him
something in return, either weapons, drugs, or money." Similarly,
Rosa-Valentín testified that Officer I told her of other instances
in which he would fabricate cases and arrest people to ask "for
either drugs, weapons, or money, and he told [her] that he would
always ask for weapons."
Rosa-Valentín next gave her version of the interactions
she had with Officer I on the day of her birthday. According to
her testimony, after greeting Officer I that night, he told her
14 Rosa-Valentín worked as a restaurant waitress at the time of her testimony. She was asked whether she had a romantic relationship with Officer I. She answered: "No, never." She was also asked about the extent of her relationship with Delgado, and she said that Delgado "was a friend of her brother" but that Delgado and she did not "have a relationship as friends."
that "he was [on duty] in a [nearby] park so he could spend some
time with us at the [party]." While at the party, she said that
Officer I had around eight or nine beers. She stated that, at some
point, a police sergeant drove by the party, but that the party was
allowed to continue until 4:30 a.m. after Officer I spoke to the
sergeant. Officer I left the party at around 1:30 or 2:00 a.m.,
but came back later. After the establishment where the party was
being held had closed, Rosa-Valentín's guests (including Officer I)
went to her house and continued the gathering until 6:00 a.m.
Before the party was over, Officer I mentioned to Rosa-Valentín
that he would come back the next day because he needed to talk to
According to Rosa-Valentín's testimony, Officer I came to
her house the next day. Her account of that visit was as follows:
He came in [driving] the patrol car, like he always did, wearing his uniform. . . . He asked me if I could get some police officers for him . . . . He asked me if I could get some for him to do some part-time work, and I told him I would check, because I have a friend who already had part-time jobs. They worked at gas stations, that kind of thing. Again, he emphasized whether I had the phone number, whether I had it in a safe place. I said I did. And he told me that if anything came up, that I should call him, that he was offering me $5,000 for every cop that I brought to him.
Rosa-Valentín also stated that Officer I persistently followed up
on his inquiry: "during the day he would come three, four, five,
six, seven times . . . then at night he would come in a patrol
car." Officer I kept this routine up for four months, beginning in
February and ending in mid-June.
Lastly, Rosa-Valentín testified that, when she refused to
provide any information to Officer I, he invited her to do part-
time work herself. She said that, when she asked what the part-
time work would be, Officer I told her to go to an apartment in the
municipality of Guaynabo, "and [that] he would talk to [her] over
there." Officer I also told her that she could go to the apartment
with her kids, that there was a pool and a tennis court in the
complex, and that they would have a good time there.
After a brief examination by the government, the district
court found Rosa-Valentín's testimony inadmissible under Fed. R.
Evid. 608(b).15 In so ruling, it rejected defense counsel's
argument that Rosa-Valentín's testimony directly contradicted
portions of Officer I's testimony. Counsel further argued that
Rosa-Valentín's testimony was relevant to Delgado's entrapment
defense. But the court ruled the entire testimony to be "nothing
else but an attempt to circumvent Rule 608."
15 The defendants argued that the evidence was admissible under Rules 404 and 613. The government stated that Rule 404 was inapplicable because Officer I was not a defendant, and the court agreed. The court sua sponte found Rule 613 inapplicable without explaining its reasoning.
2. Applicable Law and Analysis
We review the district court's evidentiary findings for
abuse of discretion, United States v. Pelletier, 666 F.3d 1 , 5 (1st
Cir. 2011), and reverse when, among other reasons, a decision rests
on an erroneous conclusion of law. See, e.g., United States v.
Pires, 642 F.3d 1 , 10 (1st Cir. 2011). Where, as here, a defendant
challenges a conviction on account of an evidentiary error, the
verdict will not be overturned if "it is highly probable that the
error did not affect the verdict." United States v. Pridgen, 518
F.3d 87 , 91 (1st Cir. 2008). Put differently, "even if [an
evidentiary] error occurred, it would not serve to overturn a
conviction if it ultimately proved harmless." United States v.
Landrón-Class, 696 F.3d 62 , 68 (1st Cir. 2012). In this case,
Delgado has demonstrated error, and the government has not met its
burden of showing that the error was harmless. See United States
v. Meises, 645 F.3d 5 , 24 (1st Cir. 2011).
Our inquiry revolves around Rule 608(b), which in
pertinent part prohibits the admission of extrinsic evidence "to
prove specific instances of a witness's conduct in order to attack
or support the witness's character for truthfulness." Fed. R.
Evid. 608(b) (emphasis supplied). The phrase "character for
truthfulness" was incorporated into the Rule by amendment in 2003.16
16 In pertinent part, the prior rule read as follows: "Specific instances of the conduct of a witness, for the purpose of attacking or supporting the witness' credibility . . . may not be proved by
The amendment sought to conform the Rule's language to the
drafters' original intent, which was to exclude extrinsic evidence
of a witness's general propensity for honesty and truth, rather
than particular instances of honesty or dishonesty used for other
non-propensity purposes. See Fed. R. Evid. 608(b) advisory
Rule 608(b) was thus amended to do away with the mistaken
notion that its reach extended to extrinsic evidence offered for
general impeachment purposes, such as, for example, contradictions,
prior inconsistent statements, bias, or mental capacity. Id.
After the amendment, courts routinely find Rule 608(b) inapplicable
to general impeachment evidence. See, e.g., United States v.
Taylor, 426 F. App'x 702 , 706 (11th Cir. 2011) (per curiam)
(holding that Rule 608(b) did not bar testimony that contradicted
defendant's story); United States v. Skelton, 514 F.3d 433 , 441-42
(5th Cir. 2008) (stating that Rule 608(b) is inapplicable in
determining the admissibility of evidence introduced to contradict
a witness's testimony as to a material issue); United States v.
Magallanez, 408 F.3d 672 , 680-81 (10th Cir. 2005) (holding Rule
608(b) inapplicable because "the evidence was introduced not to
'attack' the witness's 'character'" but to demonstrate that a
statement made during direct examination was false).
We examine the excluded testimony against this backdrop.
As previously stated, Delgado avers that Rosa-Valentín's testimony
contradicted Officer I's in several respects, and it is clear from
the record that this was the case. Officer I, among other things,
disavowed constantly visiting Rosa-Valentín after her birthday,
whereas in her proffer she stated that it was precisely thereafter
that Officer I harassed her for approximately four months,
insisting that he be provided with contact information of police
officers to do part-time work, sometimes going to her house more
than seven times per day. Rule 608(b) does not preclude the
introduction of this type of impeachment evidence. See Taylor, 426
F. App'x at 706; Skelton, 514 F.3d at 441-42; Magallanez, 408 F.3d
More importantly, however, we agree with Delgado that
Rosa-Valentín's testimony would have shown how Officer I went about
his participation in Operation Guard Shack and would thus support
her entrapment defense. See United States v. Rizvanovic, 572 F.3d
1152 , 1155 n.1 (10th Cir. 2009) ("Rule 608(b) does not bar
extrinsic evidence to the extent it goes to substantive issues, and
here the rebuttal evidence tended to disprove Defendant's
affirmative defense . . . ."); see also United States v.
Montelongo, 420 F.3d 1169 , 1175 (10th Cir. 2005) (finding that Rule
608(b) does not preclude evidence negating a defendant's guilt).
It is black-letter law that an entrapment defense has two
elements: "'(1) government inducement of the accused to engage in
criminal conduct, and (2) the accused's lack of predisposition to
engage in such conduct.'" United States v. Sánchez-Berríos, 424
F.3d 65 , 76 (1st Cir. 2005) (quoting United States v. Rodriguez,
858 F.2d 809 , 812 (1st Cir. 1988)).17 In connection with the
inducement prong, Rosa-Valentín and Delgado painted a similar
picture of Officer I's relentless pursuit of Operation Guard Shack
part-time workers. Rosa-Valentín testified that Officer I offered
her large amounts of money and pursued her for four months --
sometimes going to her house more than seven times a day -- trying
to win her over so that she would provide contact information for
part-time employees. In Delgado's case, she testified that Officer
I courted her almost daily for approximately one month before she
capitulated. See United States v. Groll, 992 F.2d 755 , 759 (7th
17 A prima facie showing of both elements is needed before a district court may instruct the jury to consider the defense. United States v. Dávila-Nieves, 670 F.3d 1 , 9 (1st Cir. 2012). In this case, the district court found that Delgado satisfied her prima facie burden through her testimony, and thus instructed the jury to consider her entrapment defense. Demarcating the contours of the entrapment defense, the Supreme Court has noted that "'[a]rtifice and stratagem may be employed to catch those engaged in criminal enterprises.'" Jacobson v. United States, 503 U.S. 540 , 548 (1992) (quoting Sorrells v. United States, 287 U.S. 435 , 441 (1932)). Nonetheless, the Court has cautioned law enforcement officers and prosecutors that "[i]n their zeal to enforce the law, however, Government agents may not originate a criminal design, implant in an innocent person's mind the disposition to commit a criminal act, and then induce commission of the crime so that the Government may prosecute." Id.
Cir. 1993) (finding that evidence of informant calling defendant on
a daily basis for over a month requesting marijuana and threatening
the defendant constituted a colorable entrapment defense).
Delgado's and Rosa-Valentín's testimonies similarly
reflected that Officer I tried to lure them into Operation Guard
Shack activities by appealing to their long-lasting friendships.
See United States v. Wright, 921 F.2d 42 , 45 (3d Cir. 1990)
(explaining that improper inducement by law enforcement may take
the form of pleas based on sympathy or friendship). But see United
States v. Ford, 918 F.2d 1343 , 1348-49 (8th Cir. 1990) (finding
that friendship with a confidential informant is not evidence of
entrapment). Delgado's and Rosa-Valentín's testimonies also
reflected that Officer I attempted to manipulate his way around
potential targets' reluctance to participate in an Operation Guard
Shack "part-time." As to Rosa-Valentín, Officer I told her to
bring her children to the "part-time" because there was a pool and
a tennis court in the apartment where it would take place.
Concerning Delgado, she said that Officer I romantically seduced
her until she gave in to his invitations to engage in a "part-
Furthermore, Rosa-Valentín's testimony supported the
propensity prong of Delgado's entrapment defense. For example,
Rosa-Valentín's testimony showed that Officer I's pursuit of
potential Operation Guard Shack targets was not limited to corrupt
officers. In this regard, she testified that Officer I
persistently asked her for contact information of police officers,
even though she told him she knew only officers seemingly involved
in legitimate part-time work (her exact words on this were: "They
worked at gas stations, that kind of thing"). Rosa-Valentín also
testified that Officer I invited her to participate in a "part-
time" herself, despite the fact that she had no criminal record,
links to the drug-trafficking trade, or involvement with the police
force. Delgado testified similarly, stating that her untarnished
criminal record shows that she had no inclination to engage in
illegal activities before Officer I's month-long pursuit. See
Rodriguez, 858 F.2d at 815-16 (stating that the absence of a
criminal record or known links to criminal activity could show the
accused's lack of predisposition to engage in illegal conduct); see
also United States v. Gamache, 156 F.3d 1 , 10-11 (1st Cir. 1998)
Notwithstanding the above, the government argues that
"[t]he court correctly found [Rosa-Valentín's] testimony
inadmissible under Rule 608(b), which only permits inquiry into
prior conduct if the conduct is probative of the witness's
character for truthfulness or untruthfulness." But this argument
fails for at least two reasons.
First, the language just quoted from the government's
brief encompasses the entire extent of its argument before us on
Rule 608(b). We have stated many times that such a lackadaisical
effort is insufficient to carry the day. United States v.
Dellosantos, 649 F.3d 109 , 126 n.18 (1st Cir. 2011); see also
United States v. Zannino, 895 F.2d 1 , 17 (1st Cir. 1990).
Second, Rosa-Valentín's testimony fell out of Rule
608(b)'s reach, inasmuch as it supported Delgado's entrapment
defense. See 28 Charles Alan Wright & Victor James Gold, Federal
Practice and Procedure § 6113, at 47 (2d ed. 2012) ("Rule 608 does
not grant discretion to admit or exclude evidence for any non-
character purpose."). While it may be true that Rosa-Valentín's
testimony incidentally called into question Officer I's character
for truthfulness, without more, such an effect does not render the
testimony inadmissable. United States v. Abel, 469 U.S. 45 , 56
(1984) ("[T]here is no rule of evidence which provides that
testimony admissible for one purpose and inadmissible for another
purpose is thereby rendered inadmissible; quite the contrary is the
case. It would be a strange rule of law which held that relevant,
competent evidence which tended to show bias on the part of a
witness was nonetheless inadmissible because it also tended to show
that the witness was a liar.").
The government also argues that "the instances mentioned
by Rosa-Valentín were improper collateral impeachment and
inadmissible." See United States v. Cruz-Rodríguez, 541 F.3d 19 ,
30 (1st Cir. 2008) ("'It is well established that a party may not
present extrinsic evidence to impeach a witness by contradiction on
a collateral matter.'" (quoting United States v. Beauchamp, 986
F.2d 1 , 3 (1st Cir. 1993))). But the government's brief contains
no explanation whatsoever as to why or how Rosa-Valentín's
testimony constituted collateral evidence. Its argument in this
regard was perfunctory at best. In fact, it was limited to the
introductory remarks just quoted and a few parenthetical citations.
See Dellosantos, 649 F.3d at 126 n.18 (stating that perfunctory,
undeveloped arguments are deemed waived). All the same, we have
already established that significant portions of Rosa-Valentín's
testimony showed how Officer I performed as an Operation Guard
Shack agent and thus provided support to Delgado's entrapment
defense. Accordingly, Rosa-Valentín's testimony was anything but
collateral. See Beauchamp, 986 F.2d at 4 (stating that the term
"collateral evidence" refers to a matter which in "itself is not
relevant in the litigation to establish a fact of consequence,
i.e., not relevant for a purpose other than mere contradiction of
the in-court testimony of the witness" (internal quotation marks
omitted)); see also United States v. Williamson, 202 F.3d 974 , 979
(7th Cir. 2000) ("A matter is collateral if it could not have been
introduced into evidence for any purpose other than contradiction."
(internal quotation marks omitted)).
Lastly, the government attacks the admissibility of Rosa-
Valentín's proffer under Fed. R. Evid. 404(b)(1). Rule 404(b)(1)
prohibits the admission of "[e]vidence of a crime, wrong, or other
act . . . to prove a person's character in order to show that on a
particular occasion the person acted in accordance with the
character." According to the government, the Rule applies here
because "Delgado . . . wanted to [use Rosa-Valentín's testimony] to
show that because [Officer I] was bad in the past, he must have
been bad in this case." In so arguing, the government appears to
refer to the confessions of corrupt acts Officer I allegedly made
to Rosa-Valentín. But our prior discussion shows that the scope of
Rosa-Valentín's proffer went far beyond those admissions.18
To boot, we disagree with the view that Delgado's stated
purpose in seeking Rosa-Valentín's testimony masked an effort to
circumvent Rule 608(b).19 In so ruling, the district court abused
its discretion by relying on an incorrect interpretation of both
the relevant facts and the applicable law. Moreover, we agree with
18 The government's brief fails to address Delgado's contention that Rule 404(b)(1) has a so-called reverse evidence prong that permits the admission of Rosa-Valentín's testimony. Given our conclusion here, we need not reach this issue. Nevertheless, we note that, in the past, the government itself appears to have sanctioned the reverse evidence argument Delgado advances. See United States v. Stevens, 935 F.2d 1380 , 1404 (3d Cir. 1991) ("[T]he government submits, the defense may introduce evidence [under Rule 404(b)] that the government induced others to commit crimes in order to show that the defendant was induced to commit the charged offense."). 19 We recognize that our discussion does not exhaust the myriad of possibilities in which the Federal Rules of Evidence could affect the admissibility of Rosa-Valentín's testimony at trial. Our analysis is limited, as it must be, to the arguments the parties raise on appeal.
Delgado's proposition that Rosa-Valentín's proffered testimony
would have corroborated pivotal elements of her entrapment defense.
Because the government does not, and cannot, challenge such a
proposition, we comfortably find that the government has not met
its burden of showing that "it is highly probable that the
[evidentiary] error did not affect the verdict." See Pridgen, 518
F.3d at 91. This finding mandates that Delgado's conviction be
Of course, nothing in this decision should be interpreted
as an intimation on our part as to the merits of Delgado's
entrapment defense. All that we decide today is that the district
court erred when precluding Rosa-Valentín from testifying as part
of Delgado's defense. Delgado cannot properly be convicted without
having the opportunity to present to the jury admissible, material,
and favorable testimony bearing on her defense.
B. Rivera's Challenge to the Special Jury Verdict Instructions
We now turn to the first of Rivera's several claims on
appeal. Among other things, Rivera argues that the district court
failed to properly instruct the jury that in answering a post-
verdict "special" question regarding drug quantity, they needed to
be sure of the quantity beyond a reasonable doubt. We agree.
At sidebar, before the jury was sent to deliberate,
Delgado's counsel asked the court to inform the jury that "the
amount and the type of drugs would be determined by the jury." The
court emphatically refused. It retorted: "No, no, no, no, no. Not
this case. We know it's seven kilos. I'm sorry. . . . It's seven
kilos. We counted them on the video. There's nothing to be
determined."20 The initial jury instructions and verdict form thus
left no role for the jury with respect to determining drug
quantity. In fact, at that juncture, the court made no reference
to quantity, explaining to the jury that the conspiracy count only
had two elements:
For you to find a defendant guilty of conspiracy, you must be convinced that the Government has proven each of the following things beyond a reasonable doubt. First, that the agreement specified in the indictment and not some other agreement existed at least between two people to commit that crime. . . . Second, that each of the defendants willfully joined in that agreement.
No one objected, and the jury returned a guilty verdict on all
The court then stated in open court that it would dismiss
the jury unless the parties had any other motions. The government
took the opportunity to request "a special jury [verdict] on the
amount of narcotics involved in this case." The court initially
refused, reasoning that photos of record showed the duffle bag
containing the seven packages of purported cocaine. But the
20 The video itself does not support the court's remarks. It shows only the four "bricks" the purported buyer placed on top of the coffee table.
prosecution insisted that the quantity issue was for the jury to
determine beyond a reasonable doubt. Delgado's counsel initially
resisted, stating that "[t]he verdict ha[d] been rendered." But,
after a short colloquy with the government and the court, counsel
agreed that the question was proper. The court acquiesced and
immediately addressed the jury: "Members of the jury, the court has
decided to ask you an additional question. Let me prepare a short
question for you to answer. You have to go back and answer only
this question. It's like another deliberation under the same terms
The court instructed the jury thereafter: "I want you to
determine, answer an additional question that's going to be typed
out, how much narcotics were involved in this case. Two choices,
less than five kilograms of purported cocaine or more than five
kilograms of purported cocaine." There were no trial objections to
these jury instructions.
After a nineteen-minute deliberation, the jury returned
21 Before submitting the special verdict form to the jury, the court asked the parties to comment on the following proposed jury question: "how much narcotics were involved in this case, less than five kilograms of purported cocaine[;] more than five kilograms of purported cocaine." Rivera's counsel objected on the basis that the record contained no evidence about the weight or amount of the purported drugs. But the court discarded the objection and sternly remarked: "Counsel, listen to me. Listen to me. That is a sentencing issue, not to be discussed today."
a verdict of "more than five kilograms of purported cocaine."22
2. Applicable Law and Analysis
a. Alleyne Error Regarding the Jury Instructions
Generally, we review challenges to the propriety of jury
instructions de novo. United States v. Whitney, 524 F.3d 134 , 138
(1st Cir. 2008). However, where, as here, a defendant fails to
properly preserve an objection at trial, we review the record under
the plain-error standard. United States v. Medina-Martinez, 396
F.3d 1 , 8 (1st Cir. 2005); see also United States v. Cotton, 535
U.S. 625 , 631-34 (2002) (applying plain-error review to an
unpreserved Apprendi error); United States v. Harakaly, 734 F.3d
88 , 94 (1st Cir. 2013) ("This court reviews unpreserved Apprendi
errors for plain error and preserved Apprendi errors for harmless
error. Since Alleyne is an extension of the Apprendi doctrine, the
same standards should apply to Alleyne errors." (internal citation
22 Consistent with the district court's instruction, the form given to the jury was titled, "Special Verdict," and included the question "[h]ow much narcotics were involved in this case." Two options were given: "less than 5 kilograms of purported cocaine," or "more than 5 kilograms of purported cocaine." The jury returned the form with an "x" marked beside the latter option. 23 Although an Apprendi issue -- namely, that drug quantity should be determined by the jury and not the judge -- was raised at trial by Delgado's counsel as well as by the government (prompting the court to require the jury to answer the special verdict question), Rivera concedes that he did not raise the instructional issue at trial. Rivera did in fact object to the special verdict question, but only on the basis of the lack of evidence as to the weight or amount of the purported cocaine. There was no trial objection
The plain-error standard requires an initial showing of
three elements: (1) that an error occurred; (2) that the error was
clear or obvious; and (3) that the error affected substantial
rights or the outcome of the case. See United States v.
Sánchez-Maldonado, 737 F.3d 826 , 828 (1st Cir. 2013); United States
v. Rodriguez, 675 F.3d 48 , 64 (1st Cir. 2012); Whitney, 524 F.3d at
140 (citing United States v. Olano, 507 U.S. 725 , 732-34 (1993)).
Even if those requirements are satisfied, however, we have the
discretion to affirm the ruling if "'the error does not distort the
fairness or integrity of the lower court proceedings in some
extreme way.'" Rodriguez, 675 F.3d at 64 (quoting United States v.
Kinsella, 622 F.3d 75 , 83 (1st Cir. 2010)). "This multi-factor
analysis makes the road to success under the plain error standard
rather steep; hence, reversal constitutes a remedy that is granted
sparingly." United States v. Gelin, 712 F.3d 612 , 620 (1st Cir.
2013). This appeal, however, falls within the realm of those
infrequent cases in which reversal is warranted.
As stated above, Rivera premises his challenge on the
district court's failure to instruct the jury that the government
needed to prove drug quantity beyond a reasonable doubt. The
reasonable-doubt standard, stemming from the Fifth Amendment’s Due
regarding the burden of persuasion and the failure to instruct the jury that drug quantity needed to be determined beyond a reasonable doubt. Accordingly, Rivera concedes in his supplemental brief that the plain-error standard applies to the Alleyne issue concerning the jury instructions.
Process Clause, is interwoven with the Sixth Amendment’s promise of
a jury verdict. See Sullivan v. Louisiana, 508 U.S. 275 , 278
(1993) ("It would not satisfy the Sixth Amendment to have a jury
determine that the defendant is probably guilty, and then leave it
up to the judge to determine . . . whether he is guilty beyond a
reasonable doubt."). It is therefore well settled that, in a
criminal case, a vital part of a judge's responsibilities is to
provide the "reasonable doubt" charge to the jury. See Dunn v.
Perrin, 570 F.2d 21 , 25 (1st Cir. 1978) (citing In re Winship, 397
U.S. 358 , 364 (1970)). Indeed, where a trial judge fails to
instruct the jury that all the elements of the charged crime must
be proven beyond a reasonable doubt, a finding of reversible plain
error may be proper. See United States v. Hellman, 560 F.2d 1235 ,
1236 (5th Cir. 1977); United States v. Howard, 506 F.2d 1131 , 1133-
34 (2d Cir. 1974).
Prior to the Supreme Court's decision in Apprendi v. New
Jersey, 530 U.S. 466 (2000), this court did not consider "drug
quantity" to be an element of the offense for purposes of the
penalties prescribed in 21 U.S.C. § 841(b)(1). See, e.g., United
States v. Eirby, 262 F.3d 31 , 36 (1st Cir. 2001). Rather, "drug
quantity" was considered to be a "sentencing factor" that the
sentencing judge could determine by a preponderance of the
evidence. See id. (explaining that pre-Apprendi, the specific drug
quantities in § 841(b)(1)'s penalty scheme did not have to be
charged in the indictment or found by the jury).
In Apprendi, the Supreme Court held that "[o]ther than
the fact of a prior conviction, any fact that increases the penalty
for a crime beyond the prescribed statutory maximum must be
submitted to a jury, and proved beyond a reasonable doubt." 530
U.S. at 490. Two years later, in Harris v. United States, 536 U.S.
545 (2002), the Supreme Court declined to extend the Apprendi rule
to facts that increase only the mandatory minimum sentence. See
id. at 565-69. While this appeal was pending, however, the Supreme
Court expressly overruled Harris in Alleyne, holding that any fact
that increases the mandatory minimum is an element that must be
submitted to the jury and proved beyond a reasonable doubt. See
Alleyne, 133 S. Ct. at 2155, 2162-63.24 Here, Alleyne applies
retroactively to Rivera's claims on appeal. See Griffith v.
Kentucky, 479 U.S. 314 , 328 (1987) ("[A] new rule for the conduct
of criminal prosecutions is to be applied retroactively to all
cases . . . pending on direct review or not yet final . . . .");
Pena, 2014 WL 448439 , at *6 ("The Alleyne rule applies to cases
pending on direct appeal at the time it was decided."); United
States v. Doe, No. 12-2304, 2013 WL 6697824 , at *12 (1st Cir. Dec.
20, 2013) ("As Alleyne was decided during the pendency of [the
defendant's] appeal, we apply it here."); Harakaly, 734 F.3d at 94
24 We examine the development of the Supreme Court's jurisprudence from Apprendi to Alleyne in more detail in United States v. Pena, No. 12-2289, 2014 WL 448439 , at *4-*6 (1st Cir. Feb. 5, 2014).
On Counts One and Two, Rivera was convicted of conspiring
and attempting to possess cocaine with the intent to distribute it.
See 21 U.S.C. §§ 841(a)(1), 846. Section 841 prohibits, among
other things, possession with intent to distribute a controlled
substance. Id. § 841(a)(1). In § 841, subsection (b) prescribes
the penalties for violations of subsection (a). Id. § 841(a)-(b).
For possession with intent to distribute cocaine, paragraph §
841(b)(1) sets out three different ranges of prison terms,
depending on the quantity of cocaine involved. Id. § 841(b)(1)(A)-
For an indeterminate quantity of cocaine, there is no
mandatory minimum term of imprisonment, and the maximum term is
twenty years. Id. § 841(b)(1)(C). If the violation involves 500
grams or more of a substance containing cocaine, the permissible
prison terms range from a minimum of five years to a maximum of
forty years. Id. § 841(b)(1)(B). If the violation of § 841(a)
involves five kilograms or more of a substance containing cocaine,
as charged in the indictment here, then the highest statutory range
of sentences applies: the mandatory minimum is ten years'
imprisonment, and the maximum term is life in prison. Id. §
Under Alleyne, then, the "drug quantity" question in this
case -- whether the offense involved at least five kilograms of a
substance containing cocaine -- aggravated the statutory sentencing
range, and was thus an element of the aggravated crime that was
required to be determined by the jury beyond a reasonable doubt.
See Alleyne, 133 S. Ct. at 2161 ("A fact that increases a
sentencing floor, thus, forms an essential ingredient of the
offense . . . . [T]he core crime and the fact triggering the
mandatory minimum sentence together constitute a new, aggravated
crime, each element of which must be submitted to the jury.").
In this case, the jury determined that more than five
kilograms of cocaine were involved, triggering the aggravated
sentencing range (ten years to life) under subparagraph (A). See
21 U.S.C. § 841(b)(1)(A). Based on this finding, the district
court sentenced Rivera to the mandatory minimum of ten years'
imprisonment. See id. Although the jury returned a special
verdict form indicating their finding that "more than 5 kilograms
of purported cocaine" were involved in the case, however, the trial
judge failed to instruct the jury that they were required to make
this special finding beyond a reasonable doubt. Nor can we assume
that the jury likely made such an inference, given that they were
never instructed that "drug quantity" was an element of any of the
offenses of conviction.
Nevertheless, the government argues that the special jury
verdict and its accompanying instructions cured the instructional
defect. Specifically, the government posits that the initial jury
instructions unequivocally established the government's duty to
prove each element of the underlying offense beyond a reasonable
doubt. The government thus reasons that "the district court's
[post-verdict special] instruction that deliberation would be under
the same 'terms and conditions' also called on the jury to accord
drug quantity the same treatment as the other elements of the
offense, . . . which comported with Alleyne." This argument is
flawed for at least two reasons.
First, it presumes that the jurors understood that the
court posed the special question because "drug quantity" was an
element of the underlying crime. Nothing in the record supports
that presumption. The instructions accompanying the special
question were tersely given, with the court only stating that the
jury would be asked to answer another question. The court neither
explained why the special question was being asked nor how the
jury's answer would bear in the case. Moreover, the special jury
verdict form was submitted to the jurors after they had: (1)
deliberated pursuant to the initial jury instruction; (2) rendered
a guilty verdict; and (3) been told by the court that they were
about to be dismissed. Having discharged their duties as initially
explained by the court, and without the benefit of any guidance as
to the reasons for or relevance of the new question being asked,
the jurors had no cause to understand the special verdict question
as involving another element of the offense.
Indeed, given the timing and manner in which the question
was presented, the jurors understandably may have failed to
appreciate that the additional question represented something more
than an inconsequential afterthought standing in the way of heading
home. With nothing to discredit the reasonable inference that the
jury placed little weight on the "special" question, we cannot find
that they were sufficiently put on notice of its critical import to
the case. Cf. United States v. DeMasi, 40 F.3d 1306 , 1317 (1st
Cir. 1994) (framing the dispositive inquiry in a challenge to a
district court's "beyond reasonable doubt" charge as "whether there
is a reasonable likelihood that the jury understood the
instructions to allow [a] conviction based on proof insufficient to
meet the [beyond-a-reasonable-doubt] standard" (internal quotation
Second, the government's argument places undue weight on
the phrase "under the same terms and conditions." In the
government's view, this phrase properly conveyed to the jury that
its post-verdict deliberation required a determination that the
government had proven drug quantity beyond a reasonable doubt. The
government, however, fails to articulate how such a broad phrase
conveyed such a specific message.
To be sure, the initial jury instructions properly
conveyed to the jury that it needed to find all the elements of the
underlying crime beyond a reasonable doubt. But, as stated above,
and consistent with the Supreme Court precedent applicable at the
time of trial, no one told the jury that "drug quantity" was an
element of the crime. Indeed, even the government's appellate
attorneys insist in their brief that "[d]rug quantity was not an
element of the offense here." Yet the government argues, in the
same breath, that the jury would have necessarily understood that
the special verdict question was required to be determined beyond
a reasonable doubt, based on the interplay of two instructions: (1)
the initial instruction that the jury must find the defendants
guilty beyond a reasonable doubt for "any essential element of a
crime charged," and (2) the subsequent instruction that the special
verdict question was "like another deliberation under the same
terms and conditions." To accept such an inconsistent argument
would strain credulity.
Similarly, the district court judge -- after giving the
instructions at issue, and immediately after the jury left the
courtroom to consider the special verdict question -- stated to
counsel that: "I can understand the Apprendi concerns . . . but in
a case like this one . . . I don't think you need a special
verdict. I'm doing it for the simple purpose of pleasing you, if
you will. I don't think you need that at all." If the district
judge himself -- consistent with the then-governing case law -- did
not believe that "drug quantity" was an element required to be
proved to the jury beyond a reasonable doubt, and did not
explicitly instruct the jury otherwise, then we cannot presume that
the jury made this inferential leap on its own initiative.
The initial jury instructions involved many different
"terms and conditions," spanning twenty pages of the trial
transcript. The government has failed to identify a single record
entry that would allow us to properly link the phrase "under the
same terms and conditions" back to the beyond-a-reasonable-doubt
standard explained to the jury in the initial instructions. Such
imprecise language was insufficient to do the heavy lifting
necessary to protect Rivera's Sixth Amendment right.
The government relies on United States v. Avilés-Colón,
536 F.3d 1 (1st Cir. 2008), and United States v. Pérez-Ruiz, 353
F.3d 1 (1st Cir. 2003), for the proposition that a verdict form
need not explicitly state that the beyond-a-reasonable-doubt-
standard governs the verdict, if the jury instructions sufficiently
conveyed the same information. This reliance is misplaced. On the
contrary, both cases weigh heavily against the government.
In Avilés-Colón, we rejected the proposition that a
verdict form needed to explicitly state that the beyond-a-
reasonable-doubt standard would govern the jury's deliberations,
when the jury instructions at issue were "suitably focused" and
properly "conveyed the need to make the finding with that level of
certainty." 536 F.3d at 27. Unlike this case, however, the
instruction in Avilés-Colón adequately framed "drug quantity" as an
essential element of the case and made the necessary linkage with
the reasonable-doubt standard. The relevant portion of the
instruction speaks for itself:
For you to find the defendant guilty of this crime, you must be convinced that the Government has proved each of the following beyond a reasonable doubt: . . . fourth, that the quantity of the substance was at least one kilogram or more of heroin, five kilograms or more of cocaine, and a detectable amount of marijuana.
Id. at 26 n.20.
Pérez-Ruiz provides no better help for the government, as
it also makes plain that jury instructions must provide a clear
linkage between the beyond-a-reasonable-doubt standard and the
proof that must be marshaled in connection with the elements of the
crime. See Pérez-Ruiz, 353 F.3d at 16, 19-20 (vacating the
appellant's sentence, in the context of an enhanced sentencing
range for a particular quantity of drugs, when the jury
instructions failed to "forge the necessary link" between the "drug
types and quantities" alleged in the indictment and "the
requirement that these facts be proven beyond a reasonable doubt").
The instructional error in this case, moreover, is not
mitigated by the fact that Rivera's ten-year sentence happened to
also fall within the statutory range (zero to twenty years of
imprisonment) for an indeterminate quantity of cocaine. See
Alleyne, 133 S. Ct. at 2162 (reasoning that when a fact "aggravates
the legally prescribed range of allowable sentences, it constitutes
an element of a separate, aggravated offense that must be found by
the jury, regardless of what sentence the defendant might have
received if a different range had been applicable"). The Alleyne
Court emphasized that whether a defendant could have received the
same sentence without the aggravating fact "is no answer" and "is
beside the point." See id. ("Indeed, if a judge were to find a
fact that increased the statutory maximum sentence, such a finding
would violate the Sixth Amendment, even if the defendant ultimately
received a sentence falling within the original sentencing range
(i.e., the range applicable without that aggravating fact).").
Under these circumstances, reversal is warranted even on
plain-error review.25 Given Alleyne's clear holding that facts
which increase mandatory minimum sentences must be submitted to the
jury and found beyond a reasonable doubt, see id. at 2163, it was
an obvious error to fail to properly instruct the jury that they
were required to determine the special verdict question beyond a
reasonable doubt. And since the district court sentenced Rivera to
the enhanced mandatory minimum sentence of ten years -- based on an
aggravating fact (drug quantity) that was not found beyond a
reasonable doubt, and for which scant evidence was presented -- the
25 See Rodriguez, 675 F.3d at 64. As we have previously noted, "[i]t may seem strange to talk about plain error, given how Alleyne came down after [the] defendants argued these consolidated appeals to us." United States v. Acosta-Colón, No. 10-1076, 2013 WL 6654386 , at *15 n.12 (1st Cir. Dec. 18, 2013). Nonetheless, we apply Alleyne's holding retroactively under the plain-error standard. See id.
error affected Rivera's substantial rights and the outcome of his
Likewise, we cannot say that the error did not "'distort
the fairness or integrity of the lower court proceedings in some
extreme way.'" See Rodriguez, 675 F.3d at 64 (quoting Kinsella,
622 F.3d at 83). The evidence on the "drug quantity" question here
was far from overwhelming and uncontroverted. See Cotton, 535 U.S.
at 631-33 (applying the fourth prong of the plain-error test, and
stating that where evidence of a statutory element -- such as drug
quantity -- is "'overwhelming'" and "'essentially uncontroverted,'"
there is "'no basis for concluding that the error seriously
affected the fairness, integrity or public reputation of judicial
proceedings'" (quoting Johnson v. United States, 520 U.S. 461 , 470
(1997)) (internal quotation marks and alteration omitted)); cf.
Harakaly, 734 F.3d at 95-97 (holding that an Alleyne error was
harmless when "the evidence of the triggering drug quantity was
overwhelming"); Pérez-Ruiz, 353 F.3d at 17-20 (vacating the
appellant's sentence after concluding that the government failed to
26 Indeed, at sentencing, the district court acknowledged that the statutory minimum may be "high" and representative of "an imperfect system," but stated that the court was nonetheless bound by the minimum. The court remarked to Rivera's counsel that: "If you find a case that says I can do away with the statutory minimum," or any case saying that "I can do what I want other than the statutory minimum, we'll deal with it. But you know very well that the statutory minimum is the statutory minimum. It's a fact." Later, the court explicitly stated that it was sentencing Rivera "to the statutory mandatory minimum on the drug count, which is 120 months."
show "overwhelming evidence" of drug quantity at trial and thus
failed to demonstrate that the Apprendi error was harmless).
While the exhibits in this case include photographs of
seven "bricks" and a duffel bag, the video of the transaction shows
only the four "bricks" that the purported buyer placed on top of
the coffee table. The video is not clear as to whether Rivera saw
or handled more than four "bricks." There was no discussion on the
video or in the preceding phone calls as to the quantity of drugs
to be transacted, and there was no testimony presented that Rivera
or Delgado were told the quantity of purported drugs involved. The
"bricks" involved in this case were fake drugs, and no evidence was
presented as to their actual weight. For example, if the seven
bricks actually weighed 0.7 kilograms each, their total weight
would be 4.9 kilograms -- just shy of the five kilograms necessary
for conviction of the aggravated offense. Therefore, as in
Pérez-Ruiz, this is not "a case in which the evidence tying the
defendant to the charged conspiracy involved drugs that were
indisputably in excess of the requisite amounts." See Pérez-Ruiz,
353 F.3d at 19.
Under these circumstances, we do not consider the
evidence of the drug quantity involved to be "overwhelming" or
"essentially uncontroverted." See Cotton, 535 U.S. at 633.
Compare Harakaly, 734 F.3d at 95-97 (finding the drug-quantity
evidence to be overwhelming when "[t]he delivery that the police
intercepted, taken alone, was nearly four times the triggering
amount," and when the defendant himself "acknowledged
responsibility for a quantity of drugs that far exceed[ed] the
triggering amount"), with Pérez-Ruiz, 353 F.3d at 17-20 (evidence
that the conspiracy involved at least five kilograms of cocaine was
not overwhelming when "actual drug quantities" were mentioned "only
three times during the trial" -- including testimony from one
witness that he supplied the drug ring with more than fifteen
kilograms of cocaine, and testimony from a DEA agent that he
estimated that the drug ring distributed "over 150 kilograms of
In sum, the record supports Rivera's contention that the
district court plainly erred in failing to instruct the jury that
the drug quantity question required a finding beyond a reasonable
doubt. In light of this instructional error, under Alleyne,
Rivera's sentence cannot stand. See Alleyne, 133 S. Ct. at 2163-
To the extent that Rivera claims entitlement to a new
trial altogether in light of this error, however, he is mistaken.
The district court's instructional error invalidates Rivera's
ten-year mandatory minimum sentence under the enhanced penalty set
out in § 841(b)(1)(A), but it does not call into question the
validity of his underlying conspiracy and attempt convictions under
§§ 846 and 841(a).
Neither conspiracy nor attempt includes "drug quantity"
as an element of the core offense. Under § 846, any person who
either attempts or conspires to commit a drug offense shall be
subject to the same penalties as the target offense. 21 U.S.C.
§ 846. We have previously held that a conviction for criminal
attempt under § 846 requires proof of only two elements: "(1) an
intent to engage in criminal conduct and (2) conduct constituting
a 'substantial step' toward the commission of the substantive
offense that strongly corroborates the criminal intent." United
States v. Dworken, 855 F.2d 12 , 17 (1st Cir. 1988) (emphasis
omitted); United States v. Rivera-Sola, 713 F.2d 866 , 869 (1st Cir.
To secure a conspiracy conviction under § 846, the
government must prove that: "(1) a conspiracy existed; (2) the
defendant had knowledge of the conspiracy; and (3) the defendant
knowingly and voluntarily participated in the conspiracy." United
States v. Maryea, 704 F.3d 55 , 73 (1st Cir. 2013) (citing
Dellosantos, 649 F.3d at 116). Accordingly, the government need
not prove a particular drug quantity in order to secure a
conviction for the core offenses of conspiracy or attempt to commit
a drug crime. See, e.g., United States v. Daniels, 723 F.3d 562 ,
564, modified in part on reh'g, 729 F.3d 496 (5th Cir. 2013)
("[D]rug quantity is not an essential element of a conspiracy
offense."); United States v. Yeje-Cabrera, 430 F.3d 1 , 12-13 (1st
Cir. 2005) (rejecting the argument "that unless the jury has found
a specific quantity of drugs, a defendant cannot be guilty of
conspiracy"); United States v. Gómez-Rosario, 418 F.3d 90 , 104 (1st
Cir. 2005) ("No specific drug quantity needs to be proven for a
jury to convict a defendant of conspiracy to possess with intent to
Therefore, under Apprendi and Alleyne, drug quantity is
an element for purposes of the aggravated penalties under §§
841(b)(1)(A) and 841(b)(1)(B), but it is not an element necessary
for conviction of the core offenses under §§ 841(a) and 846. See
Daniels, 723 F.3d at 573 ("[W]here a defendant may be subject to
enhanced statutory penalties because of drug quantity or type, the
requisite fourth 'element' under Apprendi is not a formal element
of the conspiracy offense."); United States v. González-Vélez, 466
F.3d 27 , 35 (1st Cir. 2006) ("The quantity of drugs is not an
element of conspiracy under § 846, nor is it an element of the
underlying controlled substances offense under § 841(a)(2).");
United States v. Collins, 415 F.3d 304 , 314 (4th Cir. 2005) ("Guilt
of the substantive offense defined in § 841(a) is not dependent
upon a determination of the amount or type of narcotics
distributed."); United States v. Toliver, 351 F.3d 423 , 430 (9th
Cir. 2003), abrogated on other grounds by Blakely v. Washington,
542 U.S. 296 (2004) ("[D]rug quantity and type need only be treated
as 'functional equivalent[s]' of formal elements of an offense when
a particular drug type or quantity finding would expose a defendant
to an increased maximum statutory sentence, as they do not
constitute formal elements of separate and distinct offenses under
In Alleyne itself, the defendant was charged, among other
things, with using or carrying a firearm in relation to a crime of
violence, under 18 U.S.C. § 924(c)(1)(A). Alleyne, 133 S. Ct. at
2155. That provision carries a default minimum of five years'
imprisonment. 18 U.S.C. § 924(c)(1)(A)(i). However, it also
includes two enhanced penalties if additional aggravating facts are
found: a minimum of seven years of imprisonment "if the firearm is
brandished," and a minimum of ten years "if the firearm is
discharged." Id. § 924(c)(1)(A)(ii)-(iii). The jury indicated on
the verdict form that Alleyne had used or carried the firearm, but
did not indicate that the gun was "brandished." Nonetheless, the
district court found by a preponderance of the evidence that
Alleyne had brandished the gun, and thus sentenced him to seven
years' imprisonment. The Supreme Court held that the Sixth
Amendment requires that the sentencing enhancement for brandishing
the gun must be found by the jury beyond a reasonable doubt.
Alleyne, 133 S. Ct. at 2163-64. Despite the fact that
"brandishing" was an "element" not found by the jury beyond a
reasonable doubt, however, the Court did not vacate Alleyne's
conviction. Rather, it "remand[ed] the case for resentencing
consistent with the jury's verdict." Id. at 2164.
Thus, Alleyne in effect recognizes a distinction between
"core crimes" and "aggravated crimes." See id. at 2161. In order
to subject a defendant to the enhanced penalty of an aggravated
crime, the aggravating element must be submitted to the jury and
found beyond a reasonable doubt. See id. at 2161-63. Failure to
do so invalidates the conviction as to the aggravated crime, but
does not necessarily undermine the defendant's conviction for the
core crime. See id. at 2161-64 (vacating the defendant's sentence
for the "aggravated crime" of brandishing a firearm -- when that
aggravating element was found by the judge rather than the jury --
and remanding for resentencing consistent with the jury's verdict
of guilty on the "core crime" of using or carrying a firearm); see
also United States v. McCloud, 730 F.3d 600 , 604 (6th Cir. 2013)
("[T]he discussion in Alleyne to the effect that brandishing is an
element rather than a sentencing factor was for purposes of the
Court's Sixth Amendment analysis; it did not mean that Alleyne's
conviction had to be reversed.").
Here, as in Alleyne, the enhanced penalty for the
aggravated offense is unavailable due to the absence of a beyond-a-
reasonable-doubt jury determination on the aggravating element;
however, the convictions on the core offenses remain sound.
Accordingly, Rivera's valid attempt and conspiracy convictions,
without more, subject him to the default statutory range of
penalties under § 841(b)(1)(C), regardless of the drug quantity
When faced with similar Apprendi and Alleyne claims,
circuit courts have likewise reasoned that a successful appellant
is not entitled to a new trial, but rather is only entitled to
resentencing under the default penalty provision, § 841(b)(1)(C).
See, e.g., Daniels, 723 F.3d at 572 (concluding, post-Alleyne, that
the government's failure to prove drug quantity under § 841(b) does
not undermine conspiracy convictions under §§ 846 and 841(a), but
rather "only affects the sentence"); United States v. Kelly, 519
F.3d 355 , 363 (7th Cir. 2008) ("[T]he remedy for a failure of proof
that a defendant possessed a particular amount or type of cocaine
would not be to grant him a judgment of acquittal or a new trial,
but rather to remand for re-sentencing subject to the default
statutory maximum term of twenty years."); Gómez-Rosario, 418 F.3d
at 108-09 (affirming the defendant's conviction, but remanding for
resentencing when the district court had improperly considered at
sentencing facts not found by the jury, including the amount of
heroin involved); Collins, 415 F.3d at 314 ("Because the conviction
of conspiracy to violate § 841(a) is sound, remanding for a new
trial is not the appropriate remedy."); Pérez-Ruiz, 353 F.3d at 17
("Because the issue of drug type and quantity was not properly
submitted to the jury, the statutory maximum remained at 20 years."
(citing 21 U.S.C. § 841(b)(1)(C))); Toliver, 351 F.3d at 431
("[A]lthough the government failed to prove any of the specific
drug quantities or that cocaine base/crack was involved in the
conspiracy, the defendants were not entitled to a judgment of
acquittal; rather, the district court was restricted in the maximum
sentence it could impose."); cf. Pena, 2014 WL 448439 , at *9
(collecting cases that found error under Apprendi and Alleyne and
remanded to the district court for resentencing).
The determination that Rivera is not entitled to a
retrial does not end our inquiry into the proper remedy, however.
At a minimum, under Alleyne, Rivera is entitled to resentencing
under § 841(b)(1)(C)'s default sentencing range. But Rivera's
interests are not the only interests implicated here. In light of
the reversal for procedural error, the government also has an
interest in potentially retrying Rivera for the aggravated crime
charged in the indictment. Cf. United States v. Tateo, 377 U.S.
463 , 466 (1964) ("Corresponding to the right of an accused to be
given a fair trial is the societal interest in punishing one whose
guilt is clear after he has obtained such a trial. It would be a
high price indeed for society to pay were every accused granted
immunity from punishment because of any defect sufficient to
constitute reversible error in the proceedings leading to
Because the Alleyne error here was an instructional
error, the Double Jeopardy Clause does not prohibit retrial. See
U.S. Const. amend. V.; Burks v. United States, 437 U.S. 1 , 14-15
(1978) (noting that the Double Jeopardy Clause bars retrial for
reversals due to insufficient evidence, but not reversals for
procedural trial errors such as incorrect jury instructions);
United States v. Lanzotti, 90 F.3d 1217 , 1220-24 (7th Cir. 1996)
(same); see also Tateo, 377 U.S. at 466 (explaining that where
procedural defects at trial constitute reversible error, "the
practice of retrial serves defendants' rights as well as society's
interest"). Accordingly, we believe the proper remedy is that
employed by the Fourth Circuit in Collins, which involved a failure
to submit the question of individualized drug quantity to the jury.
See Collins, 415 F.3d at 313-15.
The jury in Collins found the defendant guilty of a § 846
conspiracy to distribute crack cocaine in violation of § 841(a).
Id. at 314. The Collins district court, however, erred by failing
to properly instruct the jury regarding the determination of drug
quantity; this error affected the appropriate sentencing range
under § 841(b). Id. at 312-15. Since "[g]uilt of the substantive
offense defined in § 841(a) is not dependent upon a determination
of the amount or type of narcotics distributed," the Fourth Circuit
held that the defendant's conspiracy conviction remained valid.
Id. at 314. On that basis, the defendant was not entitled to a
retrial. Id. However, the Fourth Circuit further reasoned that it
would be inconsistent with the Sixth Amendment and Apprendi to
remand the case and permit the district court upon resentencing to
determine the quantity of cocaine for purposes of the penalties
outlined in § 841(b). Id.
For those reasons, the Fourth Circuit withheld judgment
on the conspiracy count, giving the government thirty days to
request that the court order one of two remedies: (1) affirm the
conspiracy conviction and remand for resentencing under the default
penalty provision set out in § 841(b)(1)(C), or (2) reverse the
conspiracy conviction and remand for a new trial. Id. at 315, 317.
In analogous contexts, our sister circuits have at times employed
the same remedy, giving the government the option to consent to
resentencing under a lesser sentencing range, in lieu of a remand
for a new trial. See United States v. Garcia, 37 F.3d 1359 , 1371
(9th Cir. 1994), receded from on other grounds by United States v.
Jackson, 167 F.3d 1280 (9th Cir. 1999); United States v. Orozco-
Prada, 732 F.2d 1076 , 1084 (2d Cir. 1984); Brown v. United States,
299 F.2d 438 , 440 (D.C. Cir. 1962).
We therefore will withhold judgment as to the conspiracy
and attempt counts for thirty days, during which time the
government can request either (1) that we affirm Rivera's
convictions and remand for resentencing under § 841(b)(1)(C) -- for
which there is no mandatory minimum term of imprisonment, and a
statutory maximum of twenty years -- or (2) that we vacate Rivera's
convictions and remand for a new trial, allowing the question of
drug quantity to be properly submitted to a jury.
C. Rivera's Remaining Challenges
Rivera also lodges a number of other challenges to his
conviction. Because Rivera is not entitled to a new trial on the
basis of the Alleyne error discussed above, we must consider the
additional issues that he raises on appeal: (1) that the district
court abused its discretion in denying a trial continuance, thus
violating Rivera's right to a fair trial and effective assistance
of counsel; (2) that the denial of a continuance deprived Rivera of
effective assistance of counsel at voir dire, abrogating his right
to a fair and impartial jury; and (3) that a series of evidentiary
errors cumulatively undermined Delgado's right to a fair trial.
Each of these contentions are examined in turn.
1. The Denial of a Trial Continuance
Rivera argues that the district court abused its
discretion in refusing to grant a brief continuance of the trial
date, and that this refusal violated his rights to a fair trial and
effective assistance of counsel. Although we are persuaded that
several factors weighed strongly in favor of granting the requested
continuance, we find no prejudice and thus ultimately decline to
grant Rivera relief on this issue.
The defendants were indicted on September 9, 2010. The
district court appointed Attorney Ramon L. Garay-Medina as Rivera's
counsel on October 19, 2010. The court held two status conferences
with counsel in the case: the first conference was held on November
2, 2010, during which the court scheduled the final status
conference for November 16, 2010. At that final status conference,
the court scheduled the jury trial to begin three weeks later, on
December 7, 2010. On Friday, December 3, 2010, the court advanced
the trial date by one day, rescheduling trial for 9:00 a.m. on
Monday, December 6, 2010. On that same Friday before trial, the
government filed a motion in limine to preclude the defendants from
(1) alluding to an entrapment defense during opening statements,
without first making a proffer of "some hard evidence" supporting
both elements of the entrapment defense, and (2) making any
arguments aimed at jury nullification. According to the record,
the district court neither set a deadline for a response from the
defense nor entertained oral argument on the government's motion,
which the court granted -- without explanation -- shortly before
trial on December 6, 2010.
Early in the morning on the day of trial, Rivera's
counsel filed an "emergency motion" for a one-week continuance so
as "to allow completion of the investigation, and/or preparation
for trial." In that motion, counsel complained that at the final
status conference held November 16, 2010, the court scheduled trial
for December 7, 2010, despite the protestations of "[b]oth
attorneys" that "they needed more time to adequately prepare for
this trial." Additionally, the motion described a number of other
criminal trials and cases for which Rivera's counsel was then
responsible. The motion noted that on December 3, 2010 -- the
Friday preceding the Monday trial -- the government provided
significant impeachment evidence to the defendants, amounting to
"more than 600 pages of documentation (including sanitized reports
that affect the investigation in preparation for trial)."27 Counsel
asserted that he worked "in preparation for trial during the whole
weekend," but that he "ha[d] not been able to complete reviewing
the additional material provided." Rivera suggested that the
government would not be prejudiced by a one-week delay, given that
the government "had years to investigate these cases, and prepare
them for trial." The motion also sought a court order requiring
27 Rivera's appellate brief clarified that this production included 689 pages of documents that were material to the defense (the "Brady/Giglio materials"), which the government was required to disclose to the defense pursuant to Brady v. Maryland, 373 U.S. 83 (1963) and Giglio v. United States, 405 U.S. 150 (1972). Rivera notes that the disclosure included: (1) 509 pages of payment records for Officers I and II; (2) eighteen pages of redacted FBI reports "about an investigation into a stolen car and gun ring among [Puerto Rico] undercover police, indicating that it found [Officer II]'s version of the events less than reliable"; and (3) a 162-page Puerto Rico police file of misconduct investigations against Officer I. These investigations of Officer I included two investigations from 2000, one from 2002, and a case filed in 2010 that arose from his role as an undercover agent in 2006.
the government to provide Rivera with unredacted versions of the
reports disclosed on December 3, 2010.
Immediately after the case was called for trial on
December 6, 2010, counsel for the defense asked to approach the
bench. Rivera's counsel informed the court that he had filed a
motion to continue earlier that morning. It is apparent from the
transcript that the district court had not read Rivera's motion and
had no knowledge of the government's Friday-afternoon disclosures.28
Rivera's counsel was given a brief opportunity to explain that
despite working all weekend, he and his client were not able to
complete discussions of the Brady/Giglio documents provided to the
defense by the government on Friday. Counsel noted that "[f]or
example, there is information involving the confidential services,
that there are complaints before the Supreme Court of Puerto Rico
for fabricating cases against people." Without further discussion,
the court immediately replied:
Well, let me say this: We are not going to cross that bridge before we get there. If there is an issue, a real issue that surfaces in the middle of trial that requires me to deal with it and give you whatever remedy we
28 The district court's responses indicated not only that it had failed to read the motion and consider the arguments raised therein, but also that it was not even aware that such a motion had been filed. The court inquired, "What are the circumstances? When was the motion filed?" The court repeated the question "[w]hat are the circumstances?" two more times, and also asked "What materials are we talking about? What is it you discovered? What is it that you discovered late?"
need, we'll deal with it. But a continuance is out of the question.
Given the perfunctory nature of the in-court discussion on this
issue, and without the benefit of having read Rivera's motion, the
district court denied the continuance without first learning the
scope, volume, or precise nature of the disclosed documents.
Shortly thereafter, the court addressed the potential jurors and
began the process of selecting a jury.
b. Applicable Law and Analysis
Trial courts are granted broad discretion in scheduling
trials and ruling on motions for continuances. United States v.
Maldonado, 708 F.3d 38 , 42 (1st Cir. 2013). While that discretion
is limited by a defendant's constitutional rights to testimony by
defense witnesses and effective assistance of counsel, United
States v. Orlando-Figueroa, 229 F.3d 33 , 39-40 (1st Cir. 2000),
"'only an unreasoning and arbitrary insistence upon expeditiousness
in the face of a justifiable request for delay violates the right
to the assistance of counsel.'" Maldonado, 708 F.3d at 42 (quoting
Morris v. Slappy, 461 U.S. 1 , 11-12 (1983)). Accordingly, a
district court's denial of a motion to continue trial is reviewed
for abuse of discretion. United States v. Rosario-Otero, 731 F.3d
14 , 18 (1st Cir. 2013). Under this standard, we will not disturb
such a decision if reasonable minds could disagree about the proper
ruling. See Maldonado, 708 F.3d at 42.
In evaluating a denial of a continuance, we consider
"'the reasons contemporaneously presented in support of the request
for the continuance.'" Rosario-Otero, 731 F.3d at 18 (quoting West
v. United States, 631 F.3d 563 , 568 (1st Cir. 2011)). We may also
consider a number of other relevant factors, including: the amount
of time needed for preparation compared to the actual time
available; how diligently the movant used the time available, and
whether the movant contributed to his or her perceived predicament;
the complexity of the case; other available assistance; the
probable utility of a continuance; the extent of any inconvenience
to others (including the court, witnesses, and the opposing party);
and the likelihood of injustice or unfair prejudice resulting from
the denial of a continuance. Id.; West, 631 F.3d at 568 (citing
United States v. Saccoccia, 58 F.3d 754 , 770 (1st Cir. 1995)). We
consider this final factor to be essential, overturning the denial
of a continuance only when the movant identifies specific, concrete
ways in which the denial resulted in "substantial prejudice" to his
or her defense. See United States v. Pacheco, 727 F.3d 41 , 45 (1st
Cir. 2013); Maldonado, 708 F.3d at 42; United States v. Espinal-
Almeida, 699 F.3d 588 , 615 (1st Cir. 2012); United States v.
Rodriguez-Marrero, 390 F.3d 1 , 22 (1st Cir. 2004); Saccoccia, 58
F.3d at 770.
Rivera complains that the abbreviated trial schedule left
his counsel only twelve work days to prepare for trial.29 At that
time, his trial counsel was responsible for eleven ongoing criminal
cases before the district court, ten of which were older than
Rivera's case, and six of which were pending trial. Rivera argues
that the hurried trial schedule and the denial of his motion for a
one-week continuance violated his rights to a fair trial and
effective assistance of counsel. In Rivera's view, three
developments occurred on December 3, 2010 (the Friday before trial)
that increased the prejudice of this denial: (1) the trial court
advanced the trial date by one day, from Tuesday, December 7 to
Monday, December 6; (2) the government filed a motion in limine
seeking to prohibit the defense from alluding to an entrapment
defense or a jury nullification argument; and (3) that afternoon,
the government delivered a nearly 700-page ream of partially-
redacted Brady/Giglio materials to the defense.30
29 As previously noted, on November 16, 2010, the district court held the second and final status conference in the case. At that status conference, the court first set a date for trial: December 7, 2010 -- just three weeks later. Rivera argues that the court imposed this date despite protestations from both defense counsel that they needed more time to prepare for trial. Due to the Thanksgiving holiday, and the one-day advancement, the schedule left Rivera only twelve business days to prepare. 30 Such materials are required to be disclosed to the defense when the government has in its possession evidence, including impeachment evidence, that is material to either guilt or punishment. See Giglio, 405 U.S. at 154; Brady, 373 U.S. at 87. The materials disclosed by the government included significant potential impeachment evidence concerning Officers I and II -- two
Rivera argues that the eleventh-hour production of
Brady/Giglio materials "promised a wealth of material with which to
impugn the credibility and motives of both of the [government's]
chief trial witnesses." Due to the limited time available to
review these materials, Rivera maintains that trial counsel for the
defendants were not able to put the materials to good use. Rivera
asserts that the defense thus failed to effectively establish,
among other things, that Officer I: (1) was paid over $47,000 in
benefits in excess of his police salary as compensation for his
"active pursuit" of new targets for Operation Guard Shack; (2) used
telephone calls and meetings to show his productivity to ensure the
renewal of his $1,400 in monthly payments from the FBI; and (3)
"convinced the FBI to give him a chance as an undercover agent
after getting into too much (162 pages['] worth) [of] hot water as
a local undercover officer." The last-minute disclosure also
included impeachment evidence regarding Officer II, including prior
misconduct investigations into allegations that he had abused his
undercover position to engage in criminal activities like theft and
Noting that the district court made no findings and gave
no explanation for denying the continuance, Rivera argues that any
inconvenience to the court and the opposing party from a brief
of the government's star witnesses, not just in this case, but presumably in multiple cases resulting from Operation Guard Shack.
continuance would have been minimal, given that the government had
just three witnesses -- all of whom were government agents. Rivera
further maintains that the resulting prejudice was not limited to
trial counsel's inability to put the Brady/Giglio material to good
use, but rather that the denial resulted in systemic prejudice due
to trial counsel's ineffective assistance throughout the trial.31
Rivera concludes that as a result of the district court's "'myopic
31 Throughout his brief, Rivera obliquely alludes to the allegedly ineffective assistance of his trial counsel, particularly in those sections challenging the denial of the continuance and the manner in which voir dire was conducted. However, Rivera does not squarely present ineffective assistance of counsel as a separate issue for our review on this direct appeal. Therefore, we need not consider the issue independently here. See, e.g., United States v. Williams, 630 F.3d 44 , 50 (1st Cir. 2010). Moreover, we do not generally address ineffective assistance claims on direct appeal, but instead require them to be raised on collateral review. See United States v. Neto, 659 F.3d 194 , 203 (1st Cir. 2011); United States v. Martinez-Vargas, 321 F.3d 245 , 251 (1st Cir. 2003) ("The law is firmly settled in this circuit that, as a general rule, fact-specific claims of ineffective assistance of counsel, not raised below, cannot be aired for the first time on direct appeal."). We deviate from this general practice and consider such claims on direct appeal "'only when such scrutiny of the factual record is unnecessary because the attorney's ineffectiveness is manifestly apparent from the record.'" Neto, 659 F.3d at 203 (quoting United States v. Rivera–González, 626 F.3d 639 , 644 (1st Cir. 2010)) (internal quotation marks and alteration omitted). While the record before us seems to contain at least some evidence suggesting a lack of diligence and a subpar performance on the part of Rivera's trial counsel, an ineffective assistance claim was not raised separately on direct appeal, and the record and arguments have not been not sufficiently developed on the issue. Therefore, we decline to find ineffective assistance of counsel at this time, without prejudice to Rivera's right to assert that claim in the district court through an application for collateral relief. See 28 U.S.C. § 2255; see also Neto, 659 F.3d at 203; Martinez-Vargas, 321 F.3d at 251.
insistence upon expeditiousness,'" his trial counsel was physically
present but unable to participate as an effective advocate.
(quoting Ungar v. Sarafite, 376 U.S. 575 , 589 (1964)).
For its part, the government responds that Rivera's
counsel was not diligent because he made his request for a
continuance on the first day of trial, inconveniencing the court,
the potential jurors, and the government. The government reasons
that "36 hours was sufficient time to review [the Brady/Giglio
documents] in preparation for trial." Noting that "[t]he defense
was aware of the trial date as early as November 16, 2010,
notwithstanding its single-day advancement," the government argues
that twenty days was sufficient time to prepare for a trial that
both sides agree was neither lengthy nor complex in terms of
witnesses and exhibits. Further, the government maintains that
Rivera's assertions of his counsel's ineffectiveness due to the
denial of the continuance are "speculative and insufficient to show
prejudice," and constitute a thinly-veiled ineffective assistance
of counsel claim that should not be considered on direct appeal.
Finally, the government argues that the defense's decisions may
have been the result of a deliberate strategy, and the "more likely
reason" for Rivera's conviction was the "overwhelming evidence" of
his guilt, including the video.
We agree with Rivera that several relevant factors
militated strongly in favor of granting a continuance. First, we
find that the time needed for effective preparation exceeded the
time actually available. While Rivera concedes that the case was
neither lengthy nor complex in terms of witnesses and exhibits, we
agree with him that the case involved difficult, time-intensive
questions with respect to the limits of any potentially applicable
entrapment or derivative entrapment defense, and the means
available with which to present such a defense. From the time that
a trial date was first scheduled to the day trial began, the
defense was left with only twelve business days to prepare. Rivera
asserts -- and the government has not disputed -- that at the final
status conference, the district court ignored protestations from
both defense counsel that they needed more time to prepare for
trial. To add insult to injury, without consulting the parties or
providing any explanation, on the Friday before trial the court
advanced the trial date by one day, to commence on Monday -- the
next business day.
The final blow was delivered that same Friday afternoon
by the government, when it dumped nearly 700 pages of Brady/Giglio
materials on the defense. The government has provided no
explanation or excuse for making such a voluminous disclosure on
the eve of trial, without providing the defense even a single
business day to review the redacted, 689-page production. Nor do
we think a valid excuse exists here, given that: (1) Operation
Guard Shack began as early as July 2008; (2) some of the underlying
impeachment documents, including FBI documents dated in the summer
of 2008, were in the government's possession since near the
beginning of the operation; and (3) the sham transaction for which
Rivera and Delgado were prosecuted, and which involved Officers I
and II, took place on July 24, 2009 -- one year and four months
before trial. Under these circumstances, and in the absence of any
explanation from the government, we fail to see how the eleventh-
hour provision of the Brady/Giglio disclosures here could reflect
anything other than ineptitude or strategic gamesmanship. For that
reason, the government's argument that "36 hours was sufficient
time to review [the documents] in preparation for trial" rings
The evidence before us is mixed on how diligently
Rivera's trial counsel used the twenty days (twelve of which were
business days) available to prepare for trial. Though Rivera
asserts that at the final status conference he requested more time
to prepare for trial, he waited until 3:22 a.m. on the date of
trial to file a written motion for continuance, thus contributing
to his own predicament. However, this factor is mitigated at least
in part by the developments of Friday, December 3, including the
last-minute advancement of the trial date and the government's
extensive Brady/Giglio disclosures that afternoon, which
significantly changed the landscape on the eve of trial. The
assertions by Rivera's trial counsel -- that despite having worked
all weekend, he was unable to fully review the Brady/Giglio
materials and effectively prepare for trial -- weigh in favor of
the probable utility of a one-week continuance to finish trial
preparations in light of these new disclosures.
While a one-week continuance would have resulted in some
minor inconvenience, that inconvenience is attenuated by several
facts. First, as noted by Rivera, the government had only three
witnesses, all of whom were government agents. Moreover, the
government itself, through its last-minute Brady/Giglio
disclosures, was responsible for one of the significant reasons for
a continuance. The inconvenience to the court was diminished by
the fact that the court had another trial scheduled for the same
day. Earlier that morning, the court dismissed the jury in the
other case, postponing that trial until the conclusion of Rivera's
case.32 Given also that (1) this was a relatively short, three-day
trial; (2) the district court originally set a brief, accelerated
trial schedule; and (3) no prior continuances were granted in the
case, the extent of any inconvenience stemming from a one-week
continuance would have been minimal. In sum, we find that the
32 Immediately after the bench conference in which the court denied Rivera's motion for a continuance, the court addressed the Delgado/Rivera jury: "Members of the jury, I'm sorry that I had you waiting. I had to -- I had to select a jury for another case earlier today, this morning. . . . And I did that, and I sent those people away to start that trial after we conclude this one. So now we are going to select a jury for this one and start it right away."
balance of the foregoing factors weighed overwhelmingly in favor of
granting the continuance.
Considering also that the district court did not review
Rivera's written motion, did not review the Brady/Giglio materials
disclosed, did not inquire regarding the quantity or specific
nature of the production, did not ask the government the reason for
the extreme tardiness of the disclosure, did not weigh the relevant
factors on the record, and did not entertain more than a cursory
argument on the issue, it would seem that the district court's
denial constituted "'an unreasoning and arbitrary insistence upon
expeditiousness in the face of a justifiable request for delay.'"
See Maldonado, 708 F.3d at 42 (quoting Morris, 461 U.S. at 11-12).
Nonetheless, we must consider one final factor: whether
Rivera suffered prejudice as a result of the denial. See, e.g.,
Maldonado, 708 F.3d at 42; Espinal-Almeida, 699 F.3d at 615-16;
Saccoccia, 58 F.3d at 770. "When Brady or Giglio material surfaces
belatedly, 'the critical inquiry is not why disclosure was delayed
but whether the tardiness prevented defense counsel from employing
the material to good effect.'" Pérez-Ruiz, 353 F.3d at 8 (quoting
United States v. Devin, 918 F.2d 280 , 290 (1st Cir. 1990)). To
demonstrate prejudice and overturn a verdict in the delayed
disclosure context, an appellant must show both: (1) some specific
prejudice beyond a mere assertion; and (2) that "there is a
reasonable probability that, had the evidence been disclosed to the
defense in a timeous manner or had the trial court given the
defense more time to digest it, the result of the proceeding would
have been different." Id. at 8-9.
Here, while we do not doubt that the defense would have
been better prepared to impeach the government's witnesses if there
had been more time to digest the Brady/Giglio materials, Rivera has
failed to show a reasonable probability that the outcome of his
case would have been any different if the trial court had granted
the one-week continuance. See id. Rivera cites several facts from
the Brady/Giglio disclosures -- including the undercover officers'
compensation for the operation, and investigations into prior
misconduct by Officers I and II -- that would have allowed Rivera
to further "impugn the credibility and motives of both of the chief
witnesses." However, Delgado's counsel was in fact able to impeach
Officer I's credibility by asking him, among other things, about
his FBI compensation for participating in Operation Guard Shack; in
response, Officer I testified that he received approximately $1,400
per month. During cross-examination of the Special Agent, Rivera's
trial counsel was able to ask about the alleged misconduct of both
Officers I and II prior to their involvement with Operation Guard
Shack. Therefore, the defense did in fact use the information from
the disclosures to impeach the testimony of Officers I and II.
Accordingly, in essence Rivera's claim is that -- were he given
more time to review the materials -- he would have undertaken the
same trial strategy but would have done a somewhat better job of
attacking the government witnesses' credibility.
Rivera has failed to explain how, if the Brady/Giglio
materials had been disclosed earlier or if the continuance had been
granted, he would have employed a different, more effective trial
strategy. See, e.g., United States v. Lemmerer, 277 F.3d 579 , 588
(1st Cir. 2002) (stating that an appellant cannot rely on "'wholly
conclusory assertions'" but must make at least "'a prima facie
showing of a plausible strategic option which the delay
foreclosed'" (quoting Devin, 918 F.2d at 290)); United States v.
Josleyn, 99 F.3d 1182 , 1196 (1st Cir. 1996) ("[A] principal concern
in delayed disclosure cases [is] whether the failure to supply the
information in a seasonable fashion caused the defense to change
its trial strategy." (emphasis added)).
And even if all the Brady/Giglio information had been
more effectively presented to the jury, there is not a reasonable
probability that the jury would have found that the government
failed to satisfy the elements of the offenses of conviction beyond
a reasonable doubt. Rivera does not even allege that he could have
used the Brady/Giglio material to prevent the government from
meeting its burden of proof on any element of an offense of
conviction. Moreover, he does not challenge the district court's
ruling that the entrapment defense applied only to Delgado. Nor
does Rivera argue before us now that the Brady/Giglio material
provided a factual basis for a valid derivative entrapment defense,
or indeed, any other defense.33 The information contained in the
disclosure fails to vitiate the video evidence of Rivera's
participation in the sham transaction, which was corroborated by
his codefendant's admissions at trial as well as the incriminating
testimony provided by all three witnesses for the government.
Given that Rivera does not specifically articulate how
the Brady/Giglio material at issue would have allowed him to either
(1) effectively challenge the government's burden of proof on any
element of an offense of conviction, (2) establish a foundation for
a viable defense, or (3) employ a different, more effective trial
strategy, he has failed to show a reasonable probability that the
trial's outcome would have been any different if the court had
granted his motion for a continuance. See Pérez-Ruiz, 353 F.3d at
8-9. Therefore, Rivera has failed to demonstrate specific and
substantial prejudice, and -- although we are indeed troubled by
what appears to be the district court's blind allegiance to speed
over careful consideration of Rivera's justifiable request for a
brief continuance -- his claim on this issue must ultimately fail.
See Maldonado, 708 F.3d at 42-44; Pérez-Ruiz, 353 F.3d at 8-9.
33 As this issue was not raised on appeal, we express no opinion here as to whether an entrapment or derivative entrapment defense was available to Rivera. See Williams, 630 F.3d at 50 (stating that underdeveloped arguments are deemed waived on appeal).
2. Voir Dire
Rivera further argues that the court's voir dire was
inadequate to protect his right to a fair and impartial jury and to
intelligently exercise his peremptory challenges. For the reasons
described below, we find no merit to this claim.
Rivera explicitly concedes that the court did not
improperly refuse to ask specific questions of the jurors and did
not generally employ improper procedures during voir dire. Rather,
he argues that the court's "race to trial left his counsel
apparently incapable of participating in any way, either by
suggesting issues to the Court or requesting follow up questions
about issues likely to create significant prejudice [to] his right
to a fair trial." In support of this argument, Rivera notes that
his trial counsel proposed no questions, and in fact, "did nothing"
during the voir dire process.
Rivera further argues that there were four substantive
issues that did not receive adequate attention at voir dire: (1)
the trial court should have asked more specific questions about the
jurors' knowledge of Operation Guard Shack, instead of asking just
one question concerning whether they knew about "the facts of the
case"; (2) although the court asked whether any juror worked (or
had a family member who worked) for a law-enforcement agency, the
court should have "inquired  further" into the issue; (3) the
court should have asked the jurors regarding the fact that the
video of the sham transaction included references to the San Juan
mayor as a "cokehead," which could have prejudiced jurors who
supported the mayor against the defendants; and (4) the court
should have explored the jurors' attitudes regarding homosexuality,
given that the government later presented evidence and argument
suggesting that Rivera was romantically interested in a male
Trial courts have "'broad discretion'" -- "'subject only
to the essential demands of fairness'" -- in determining how to
conduct voir dire. United States v. Misla-Aldarondo, 478 F.3d 52 ,
60 (1st Cir. 2007) (quoting Real v. Hogan, 828 F.2d 58 , 62 (1st
Cir. 1987)). The Supreme Court has "repeatedly emphasized" that
jury selection "is 'particularly within the province of the trial
judge.'" Skilling v. United States, 130 S. Ct. 2896 , 2917 (2010)
(quoting Ristaino v. Ross, 424 U.S. 589 , 594–95 (1976)).
Accordingly, "[n]o hard-and-fast formula dictates the necessary
depth or breadth of voir dire," id., and we review the trial
judge's voir dire questioning for abuse of discretion, United
States v. Sherman, 551 F.3d 45 , 49 (1st Cir. 2008) (citing United
States v. Bergodere, 40 F.3d 512 , 517 (1st Cir. 1994)). We grant
"'special deference'" to the district court's determination of jury
impartiality. Id. at 51 (quoting United States v. Moreno Morales,
815 F.2d 725 , 733 (1st Cir. 1987)).
We find no such abuse of discretion here. First, as
previously noted, the trial court did not refuse to ask any
questions requested by Rivera's counsel. Counsel requested no
questions, and even if he had, the court was entitled to "cover
the substance of the appropriate areas of concern by framing its
own questions in its own words." Real, 828 F.2d at 62 (finding
that a trial court need not "pose every voir dire question
requested by a litigant"). The record shows -- and Rivera does not
dispute -- that the court asked a series of questions to identify
potential biases and inquired as to whether prospective jurors
could be fair and impartial in deciding the case. See Sherman, 551
F.3d at 52. Thus, we find no abuse of discretion in the general
manner in which the district court chose to conduct voir dire.
We further find no merit to Rivera's four specific
allegations of deficiencies in the voir dire process. With respect
to the first two alleged deficiencies, Rivera admits that the
district court asked about each issue. While the court did not
refer to Operation Guard Shack during voir dire, it did review the
facts alleged in the indictment with the prospective jurors, and
added that the two defendants "were police officers from Puerto
Rico at the time the facts of this case allegedly occurred." The
court then asked if any of the potential jurors "have heard of
something that may be related to the facts of this case." No one
responded in the affirmative.
The court also asked if any prospective jurors were law-
enforcement officers, or had "close relatives who are law-
enforcement officers, police officers." None of the prospective
jurors indicated that they were law-enforcement officers
themselves; several told the court that they had family members who
worked in law enforcement, but that this relationship would not
affect their ability to be fair and impartial. Given that the
trial court inquired into both these issues, and in the absence of
a specific showing of prejudice or more developed argumentation, we
do not find that the district court abused its discretion in the
breadth and depth of its questioning.
With respect to Rivera's final two specific allegations
of error, regarding disparaging comments concerning the mayor of
San Juan and statements implicating Rivera's sexuality, Rivera
concedes that the district court had no reason to know that either
of these facts might become an issue in the trial. Hence, the
court could not have exceeded its "broad discretion" when it failed
to ask prospective jurors about specific facts unknown to the
court, unraised by the parties, and not yet at issue. See
Misla-Aldarondo, 478 F.3d at 60. On this record, Rivera has not
shown that the district court abused its discretion in conducting
voir dire and selecting a jury.
3. Alleged Evidentiary Errors
Finally, Rivera alleges five evidentiary errors, which
he argues cumulatively undermined his right to a fair trial. We
begin by examining each individual alleged error in turn.
a. Testimony on Suspicion of Prior Corrupt Acts
The first alleged evidentiary error identified by Rivera
concerns the testimony of the government's first witness, the FBI
Special Agent who helped set up the reverse sting. The Special
Agent testified that he was responsible for preparing the "bricks,"
the undercover apartment, and the video equipment to record the
sham transaction. Though he did not object at trial, Rivera now
complains that the Special Agent was permitted to testify that,
before approaching a target for a reverse sting, undercover agents
must have had a "reasonable suspicion" that the target was "corrupt
or involved in illegal activities or believed to be involved in
illegal activities." Rivera asserts that such testimony was not
relevant and was overwhelmingly prejudicial. He argues that the
testimony served only to suggest to the jury -- without any
supporting evidence -- that Rivera had committed some crime or
similar bad act before becoming involved in the reverse sting.
Because Rivera failed to object at trial, we review the
trial court's admission of the testimony for plain error. See
United States v. Powers, 702 F.3d 1 , 10 (1st Cir. 2012). The
plain-error test is an "exacting standard." See Long v. Fairbank
Reconstruction Corp., 701 F.3d 1 , 5 (1st Cir. 2012) ("To establish
plain error, a party must show that there was error, that it was
plain, and that it affected the party's substantial rights; an
appellate court may then notice the error only if it 'seriously
affect[ed] the fairness, integrity, or public reputation of
judicial proceedings.'" (quoting United States v. Borrero–Acevedo,
533 F.3d 11 , 15 (1st Cir. 2008))).
Rivera's argument misses the mark. The government
presented no evidence that the FBI targeted Rivera, or that any
government agents approached him to recruit him for the
transaction. Rivera was approached by his partner Delgado, who in
turn was approached by Officer I. Thus, the allegedly prejudicial
effects of which Rivera complains concerned whether the undercover
agents had a reasonable suspicion of Delgado, not Rivera. Contrary
to Rivera's argument, the Special Agent's testimony did not suggest
that Rivera himself had previously committed some crime or similar
bad act. While Rivera and Delgado were charged with conspiracy and
aiding and abetting each other, Rivera fails to explain how the
implication that the government agents may have had a reasonable
suspicion of Delgado affected Rivera's substantial rights.
Given that the two codefendants were tried together, we
do not think it improbable that an evidentiary error pertaining to
one defendant could impact the rights of the other, or that a
suggestion of corruption or criminality on the part of Delgado
could implicate Rivera by association. However, Rivera fails to
connect the dots of such a theory, or explain how this alleged
error meets the standard for plain-error review. Even assuming
that it was error to admit the testimony, Rivera has not
demonstrated that such an error was "plain," affected his
"substantial rights," and "seriously affected" the fairness,
integrity, or public reputation of the trial. See Long, 701 F.3d
at 5. Thus, his cursory argument has fallen short of the "rather
steep" road to success under the "exacting" plain-error standard.
See Gelin, 712 F.3d at 620; Long, 703 F.3d at 5.
Rivera further alleges that the Special Agent's testimony
regarding reasonable suspicion of corruption or illegal activities
violated Federal Rules of Evidence 403, 404(b), 405, 602, 701, and
802. Apart from reciting these conclusory allegations, however,
Rivera fails to specifically explain how the Special Agent's
testimony violated these evidentiary rules. We need not consider
such bare assertions on appeal. See Zannino, 895 F.2d at 17 ("It
is not enough merely to mention a possible argument in the most
skeletal way, leaving the court to do counsel's work, create the
ossature for the argument, and put flesh on its bones.").
b. Sexual Orientation Evidence
Secondly, Rivera argues that the introduction of evidence
of the defendants' respective sexual orientations violated Federal
Rules of Evidence 402 and 403 and violated his right to a fair
trial. Rivera challenges the admission of two categories of such
evidence: (1) evidence of Delgado's sexual orientation, and (2)
evidence of Rivera's sexual orientation. Where there was a proper
objection at trial, we review the district court's evidentiary
ruling for abuse of discretion; where no such objection was made,
we review for plain error. See Powers, 702 F.3d at 10.
i. Delgado's Sexual Orientation
We begin with the introduction of evidence regarding
Delgado's sexual orientation. Because the defense properly
objected to this evidence at trial, we review the admission of this
testimony for abuse of discretion. See id.
During the government's redirect examination of its first
witness (the Special Agent referred to above), the government
inquired as to whether the Special Agent knew "what Raquel
Delgado's civil status is." Delgado's counsel objected to the
questioning as irrelevant and outside the scope of Delgado's cross-
examination. Seeking to inquire further as to the reasons for
Delgado's divorce, the government proffered that "the agent
interviewed Ms. Delgado's ex-husband, and he told him that they got
divorced because she was having an affair with a female Sergeant."
The court sustained the objection, explaining that "in the context
of what we have in the case right now, it is extremely prejudicial,
beyond the facts of the case."
Later in the trial, as previously described, Delgado
testified that she had romantic affairs with Officer I, first in
2005, and then during the summer of 2009 when she was rejecting his
persistent invitations of part-time employment. Delgado testified
that in 2005, she and Officer I "had a sporadic relationship"
during which they went on dates, visited each other's homes, and
"slept together several times." She further testified that weeks
after the sham transaction, she and Officer I again had sexual
intercourse. An important component of Delgado's defense, theory
of the case, and trial strategy was that Officer I improperly
induced her to participate in the sham transaction by appealing to
their long-lasting friendship and romantic relationship.
Delgado's ex-husband also testified for the defense,
stating -- among other things -- that he and Delgado "were
boyfriend and girlfriend for almost three years, and we were
legally married for five years." He testified that he and Delgado
had children together, but eventually divorced and stopped
communicating regularly except through their children.
During its cross-examination of Delgado's ex-husband, the
government asked: "In fact, didn't you tell the FBI if they wanted
to know any details about Raquel Delgado's wife -- or rather life,
you would have to ask her girlfriend, San Juan Municipal female
Sergeant Wanda Rivera?" Delgado's counsel objected, and the court
responded: "Overruled. Isn't that what you told the agents? . . .
You have to answer the question, sir. That's not an answer. You
have to answer the question." In response, Delgado's ex-husband
answered: "What I said was that if he wanted -- if they wanted to
know about Mrs. Delgado, they should ask her friends, and Mrs.
Wanda Rivera, who would have direct information."
The government immediately pressed the point further:
"Wait a minute. You didn't tell the FBI that when you divorced
Raquel Delgado, she was having an affair with Sergeant [Rivera]."
At this point, the court overruled another objection from Delgado's
counsel, who then requested a sidebar. The court explained its
reasoning to Delgado's counsel as follows:
[N]ow it's relevant, because you are -- you are intimating in your evidence . . . that there is a man-woman relationship between the witness and your client. And I think the jury should consider whether there was a lesbian relationship between this woman and somebody else, because one thing is kind of inconsistent with the other. Usually lesbians or gay people don't cross lines to the opposite sex. Don't you think?
Counsel disagreed, and the court responded, "Well, that's what I
understand. . . . That's what I've learned and seen in my 67 years
Delgado's counsel argued that the government was trying
to elicit statements regarding Delgado's sexual orientation in
order to divert the jury's attention from facts relevant to the
defense of entrapment -- whether she had a predisposition to commit
a crime or if she was improperly induced -- to a matter (her sexual
orientation) that had no bearing on the case. Counsel continued:
"She could have a perfect relationship with this man. She had it
for 16 years. And she also had a relationship with a woman. And
that doesn't make her a criminal. . . . It doesn't make it
impossible to concede she had another male relationship." The
court replied, "[b]ut it is kind of inconsistent." When Delgado's
counsel began to argue that the evidence was "extremely
prejudicial" under Rule 403, the court concluded: "well if you're
asking under 403, the balancing is that it's relevant. Overruled."
With that, the bench conference concluded, and the government
continued asking the witness about Delgado's same-sex relationship.
The inadequacy of the district court's faulty reasoning
and Rule 403 "balancing" on this issue should be immediately
obvious from the excerpts of the trial transcript referenced above.
Nonetheless, we will spell out a few of the concerns here. The
competing arguments were effectively presented by Delgado's counsel
(in favor of exclusion) and the district court (in favor of
admission). To the extent that the disputed testimony had any
relevance to a fact of consequence in determining the case, such
putative relevance was predicated on the idea that Delgado's one
alleged homosexual relationship made it somewhat less probable that
she also engaged in a heterosexual romantic relationship with
Officer I, which in turn had some bearing on her entrapment
defense. See Fed. R. Evid. 401 ("Evidence is relevant if: (a) it
has any tendency to make a fact more or less probable than it would
be without the evidence; and (b) the fact is of consequence in
determining the action.").
Whatever limited probative value this evidence might have
had in isolation, however, was further undercut by the undisputed
testimony of Delgado's ex-husband that the two had children
together and maintained an eight-year heterosexual relationship --
including three years of dating and five years of marriage.
Regardless of what the district judge may have previously "learned
and seen in [his] 67 years of age" about "lesbians or gay people
[not] cross[ing] lines to the opposite sex," there was specific,
uncontroverted testimony in this very case that Delgado maintained
an eight-year heterosexual relationship with her ex-husband.
No evidence was presented that Delgado was not interested
in sexual relationships with men, or even that she preferred women
to men as sexual partners. Accordingly, evidence of one
relationship with another woman had -- at best -- marginal
relevance to the question whether she had a sexual relationship
with Officer I. Moreover, Delgado's entrapment defense did not
hinge solely on the sexual nature of her relationship with Officer
I, but rather also on testimony that the two had been friends since
middle school, and that Officer I appealed to this relationship and
solicited her on a near-daily basis for approximately one month
before she acquiesced to provide security for the sham transaction.
As evinced in part by the government's persistence in
hammering the largely irrelevant point of Delgado's same-sex
relationship, evidence of homosexuality has the potential to
unfairly prejudice a defendant. See, e.g., United States v.
Yazzie, 59 F.3d 807 , 811 (9th Cir. 1995) ("[E]vidence of
homosexuality can be extremely prejudicial . . . ."); United States
v. Ham, 998 F.2d 1247 , 1252 (4th Cir. 1993) ("We accept without
need of extensive argument that implications of . . . homosexuality
. . . unfairly prejudice a defendant." (footnote omitted)); State
v. Ford, 926 P.2d 245 , 250 (Mont. 1996) ("There will be, on
virtually every jury, people who would find the lifestyle and
sexual preferences of a homosexual or bisexual person
offensive. . . . [O]ur criminal justice system must take the
necessary precautions to assure that people are convicted based on
evidence of guilt, and not on the basis of some inflammatory
personal trait."); ABA Standards for Criminal Justice, Prosecution
Function and Defense Function, Standard 3–5.8(c), p. 106 (3d ed.
1993) ("The prosecutor should not make arguments calculated to
appeal to the prejudices of the jury."). Given the extremely low
probative value of the evidence pertaining to Delgado's same-sex
relationship, we think it patently obvious that its minimal
probative value was substantially outweighed by the dangers of
unfair prejudice, confusing the issues, and misleading the jury.
See Fed. R. Evid. 403.
It is true that "[w]e give great deference to a district
judge's balancing of probative value versus unfair prejudice."
United States v. Breton, No. 12-2293, 2014 WL 30517 , at *10 (1st
Cir. Jan. 6, 2014). This is the case "even when a judge does not
expressly explain the Rule 403 balancing process on the record."
Id. But while our review of a trial court's Rule 403 decision is
deferential, it "is not completely without bite." Espeaignnette v.
Gene Tierney Co., Inc., 43 F.3d 1 , 5 (1st Cir. 1994). Here, we
find that the trial court abused its discretion because, for the
reasons explained above, the court made a serious mistake in
weighing the danger of unfair prejudice against the testimony's
minimal probative value. See id.; see also Corporate Techs., Inc.
v. Harnett, 731 F.3d 6 , 10 (1st Cir. 2013).
That determination does not end the inquiry, however.
See Espeaignnette, 43 F.3d at 9. We may not disturb the verdict if
the error was harmless -- that is, if it did not affect Rivera's
substantial rights. See id.; see also Fed. R. Evid. 103(a); Fed.
R. Crim. P. 52(a). For an evidentiary error of non-constitutional
dimension, the error is harmless if we "can say 'with fair
assurance, after pondering all that happened without stripping the
erroneous action from the whole, that the judgment was not
substantially swayed by the error.'" United States v. Melvin, 730
F.3d 29, 39 (1st Cir. 2013) (quoting United States v. Sasso, 695
F.3d 25 , 29 (1st Cir. 2012)); Espeaignnette, 43 F.3d at 9. We have
such fair assurance here.
For many of the same reasons that the testimony at issue
was not highly probative of a fact of consequence in determining
the action, the testimony was unlikely to have substantially swayed
the jury's verdict as to Rivera. On the theory espoused by the
government and the district court, evidence of Delgado's sexual
orientation was introduced to impugn one aspect of Delgado's
testimony on the improper inducement element of her entrapment
defense -- whether she had a romantic or sexual relationship with
Officer I. Delgado's sexual orientation has little to do with
whether the elements of the offenses were satisfied as to Rivera or
whether Rivera had a viable defense. The trial testimony and video
provide damning evidence that Rivera participated in the sham
transaction and satisfied the elements of the offenses of
conviction. Furthermore, as previously discussed, Rivera does not
challenge the district court's ruling that no entrapment or
derivative entrapment defense was available to him. For those
reasons, the district court's error in allowing testimony as to
Delgado's sexual orientation was harmless as to Rivera, and we will
not disturb the judgment below on the basis of this error. See
Fed. R. Evid. 103(a); Fed. R. Crim. P. 52(a); Espeaignnette, 43
F.3d at 9.
ii. Rivera's Sexual Orientation
Turning to evidence of Rivera's sexual orientation, we
next consider his argument that what he deems to be "homosexual
banter" in the video of the sham transaction -- coupled with
testimony and argument which suggested that he was sexually
interested in Officer III, the male undercover agent playing the
role of the buyer -- sent a clear message to the jury about
Rivera's homosexuality in order to "prey on long-standing and
deeply rooted prejudices about homosexuals as deviants, miscreants,
sinners and criminals." Specifically, Rivera directs our attention
to three types of allegedly improper references to his sexual
orientation at trial: (1) the "homosexual banter" among the
participants depicted in the video of the sham transaction; (2) the
testimony by Officer I that Rivera wanted the phone number of
Officer III in order to give him a present and "get in touch with
him" after the sham transaction;34 and (3) the testimony by Officer
34 During its opening statement, the government referenced this expected testimony from Officer I, arguing that Rivera "was so comfortable with the situation, he want[ed] a phone number of the buyer" -- Officer III -- after the deal was over. Indeed, the government continued to stress that after the sham transaction was completed, Rivera contacted Officer I "several times" because he wanted Officer III's phone number. At that point, Rivera's counsel objected, and asked to approach the bench. The court overruled the objection without sidebar, explanation, or further discussion, instructing the government to "[g]o ahead." The government continued: "[Rivera] wants his phone number because he has a souvenir for him and wants to go out with him." Given the objection at trial, we review the district court's admission of this statement in the government's opening for abuse of discretion. See Powers, 702 F.3d at 10; see also McPheeters v. Black & Veatch
II that "Angel [Rivera] was kind of interested in the guy, the
other guy that was there" (presumably referring to Officer III).
There were no objections at trial to these three types of evidence
of Rivera's sexual orientation, so we review their admission for
plain error. See Powers, 702 F.3d at 10.
Even if it was error to admit the foregoing evidence and
argument, such an error will not permit us to overturn Rivera's
conviction if the error was harmless. See Fed. R. Crim. P. 52(a);
see also Landrón-Class, 696 F.3d at 68; United States v. York, 572
F.3d 415 , 429 (7th Cir. 2009) ("Under either a plain error standard
or an abuse-of-discretion standard, if those errors were harmless,
[appellant's] conviction will stand."). Here, we find that "it is
highly probable" that any error in allowing evidence of Rivera's
sexual orientation did not affect the verdict; thus, any such error
was harmless. See Pridgen, 518 F.3d at 91.
We agree with Rivera that evidence of his homosexuality
was "relevant to nothing." However, that same irrelevance cuts
against him on the harmless-error analysis here. Rivera's sexual
orientation had absolutely nothing to do with whether his conduct
satisfied the elements of the offenses of conviction, or whether he
had a valid defense. Rivera fails to explain -- under the
particular facts of this case -- precisely how evidence of his
Corp., 427 F.3d 1095 , 1102 (8th Cir. 2005) ("We review a district court's management of opening statements for an abuse of discretion.").
homosexuality affected the jury's guilty verdict regarding his
participation in the sham transaction.
Unlike Delgado, Rivera did not seek to support an
entrapment defense by presenting testimony and argument that an
undercover agent improperly induced him to participate in the
transaction by means of a romantic or sexual relationship. And
Rivera makes no argument that the government's evidence was
otherwise so weak that evidence of his homosexuality was likely to
have tipped the scales against him. Particularly given the highly
incriminating evidence here -- including the video recording and
the testimony of the government witnesses and his codefendant --
there is a high probability that the alleged error concerning
Rivera's homosexuality did not affect the verdict. See id.
Therefore, any such error was harmless and cannot serve to overturn
his conviction. See id.; see also Fed. R. Crim. P. 52(a); Landrón-
Class, 696 F.3d at 68; York, 572 F.3d at 429-30.
c. Requiring Delgado to Admit the Charges
In his third allegation of evidentiary error, Rivera
argues that the district court violated his right to a fair trial
when it required his codefendant Delgado to testify whether she
admitted all the allegations of the indictment. He further
maintains that "[t]he Court's sua sponte insistence on requiring
Delgado to admit her culpability to the charge that she conspired
with [Rivera] demolished the presumption of innocence to him, no
matter how she answered."
Delgado testified in her own defense at trial. During
direct examination by her counsel, with regard to the sham
transaction, Delgado admitted that she "understood that what
[Officer I] was doing was not something legal," and that she
expected that she and Rivera would each make $2,000 for their
participation. Delgado also testified that "[a]fter all this
insistence" from Officer I, she contacted Rivera, and together they
"decided to go to the place" of the transaction. She further
responded in the affirmative when her counsel asked, "Now, you were
aware those were narcotics? You realized it was something wrong
you were doing?" There were no objections to any of this
The government began its cross-examination of Delgado by
immediately asking whether she admitted to participating in the
drug transaction. She agreed, saying, "I've admitted I did it, as
I said, and I repeat, because of [Officer I's] insistence and
because of the relationship, the sentimental or romantic
relationship I had with him and my trust in him." Hearing that,
the government pressed her further: "So you admit every count in
this Indictment; is that correct?" Delgado responded, "I was
there, I repeat, I didn't --." The district judge cut her short,
interjecting, "[t]he question is whether -- we want an answer
whether you admit all the charges that are against you in this
accusation. That's all."
Delgado's counsel objected, arguing that the question
improperly elicited an answer as to the charges, although Delgado
had already entered a plea. The court overruled the objection, and
the government continued to press the point, asking whether she did
the things alleged in the indictment. Delgado continued to respond
that she "was there, and [her actions were] wrong." She admitted
that she knew the transaction involved drugs, but she did not admit
that she knew the type of drug or the quantity involved. Again,
Rivera's counsel did not object to this line of questioning.
On appeal, Rivera argues that the district court erred
by not "remain[ing] alert" to his right against self-incrimination
when Delgado waived her own right in her testimony at trial. In
Rivera's view, the district court "demolished the presumption of
[his] innocence" when it forced Delgado to admit the charges on the
stand, requiring Rivera "to rebut this powerfully incriminating
evidence." Rivera further complains that no appropriate curative
instruction was given, and argues that this was a plain error of
We agree with Rivera that it was highly improper -- for
not just the prosecution, but especially for the trial judge
himself -- to ask Delgado on the stand whether she admitted all the
charges against her. See, e.g., United States v. Levine, 180 F.3d
869, 872 (7th Cir. 1999) (stating that "the judge [must] make it
clear to the jury that neither the questioner nor the witness
defines the elements of the offense"); United States v. Espino, 32
F.3d 253 , 257 (7th Cir. 1994) (finding the question whether the
defendant was "admitting the conspiracy" to be improper because it
required a conclusion about the legal consequences of the
defendant's conduct, and not just about the predicate facts for
such a conclusion -- namely, the existence of a conspiratorial
agreement). Even assuming an error of constitutional dimension
with respect to the questions asked of Delgado, however, we find
that the government has met its burden of proving beyond a
reasonable doubt that the error did not influence Rivera's verdict.
See Melvin, 730 F.3d at 39 (quoting Sasso, 695 F.3d at 29).
With respect to the relevant testimony elicited from
Delgado on cross, she did not ultimately yield to the demands of
the prosecution and the district court to state a legal conclusion
as to whether she was guilty of the counts charged in the
indictment. Nor did she make any factual admissions that were
materially different from her testimony on direct examination.
Delgado's testimony, on both direct and cross, was consistent with
her theory of the case -- namely, that she participated in the sham
transaction, but that she was entitled to an entrapment defense
because she was improperly induced by Officer I. Therefore, the
exchange of which Rivera complains did not alter the nature or
extent of the evidence before the jury. We are convinced beyond a
reasonable doubt that the introduction of Delgado's redundant
testimony on cross did not influence the verdict; hence, any error
on this issue was harmless. See id.
d. Restriction of Cross-Examination, and Opinion Testimony from Lay Witnesses
Lastly, Rivera seeks to piggyback on Delgado's arguments
regarding two final alleged evidentiary errors: (1) that the
district court unduly restricted cross-examination to issues raised
on direct, thereby refusing to allow proper impeachment questions;
and (2) that the court erred by admitting inadmissible lay opinion
testimony from Delgado's ex-husband.
Rivera's brief devotes a grand total of five sentences to
addressing these two issues. And two of those five sentences
merely state that Rivera adopts the relevant arguments presented in
Delgado's brief. Rivera was certainly entitled to join in
Delgado's brief or to adopt by reference parts of her brief. See
Fed. R. App. P. 28(i). However, "[a]doption by reference cannot
occur in a vacuum and the arguments must actually be transferable"
from Delgado's case to Rivera's appeal. See United States v.
Brown, 669 F.3d 10 , 16 n.5 (1st Cir. 2012). "In this context,
issues that are averted to in a perfunctory manner absent developed
argumentation are waived." Id. Here, as in Brown, Rivera's
attempt to join Delgado's arguments on these two errors was
"textbook perfunctory -- he offered no explanation as to why her
arguments pertained to him." See id.
Delgado's argument on the first issue focused on her
claim that the improper limitations on the cross-examination of
Officer I "prevented Delgado  from presenting important evidence
that aided her in establishing her only defense, that she was
entrapped by [Officer I] into participating in the offense
conduct." With respect to the second issue, Delgado argued that
the admission of improper lay opinion testimony from her ex-husband
"cannot be considered harmless since precisely the matter [on]
which he expressed an opinion o[r] belief concerned the most
crucial ultimate issue of fact at trial; that the jury should
reject Delgado['s] entrapment defense based on his opinion as to
what he would do under similar circumstances." Thus, both issues
concern Delgado's sole defense of entrapment.
As previously discussed, Rivera does not appeal the
district court's ruling that no such defense was available to him.
Having failed to "'connect the arguments adopted with the specific
facts pertaining' to him," Rivera has not properly adopted
Delgado's arguments. See United States v. De La Paz-Rentas, 613
F.3d 18 , 29 (1st Cir. 2010) (quoting United States v. Bennett, 75
F.3d 40 , 49 (1st Cir. 1996)). For that reason, Rivera has waived
these two issues. See Brown, 669 F.3d at 16 n.5. Moreover, even
without a finding of waiver, we are convinced that any alleged
error with respect to these two evidentiary issues was harmless.
See Melvin, 730 F.3d at 39.
e. Cumulative Error
Having found that none of the five evidentiary errors
alleged by Rivera are individually cause for relief, we turn
finally to his claim that these errors cumulatively undermined his
right to a fair trial. We have previously accepted the
"theoretical underpinnings" of such a cumulative-error claim --
namely, that "[i]ndividual errors, insufficient in themselves to
necessitate a new trial, may in the aggregate have a more
debilitating effect." United States v. Sepulveda, 15 F.3d 1161 ,
1195-96 (1st Cir. 1993). In examining such claims, we weigh the
trial errors "against the background of the case as a whole, paying
particular weight to factors such as the nature and number of the
errors committed; their interrelationship, if any, and combined
effect; how the district court dealt with the errors as they arose
(including the efficacy -- or lack of efficacy -- of any remedial
efforts); and the strength of the government's case." Id. at 1196.
Rivera was entitled "to a fair trial, not to a mistake-
free trial." See id. Considering the nature of the errors here,
we find that these errors were largely tangential to facts material
to the jury's adjudication of Rivera's guilt. As previously
described, the government's case against Rivera was strong; it
included testimony by three government agents involved in the
sting, as well as a video depicting Rivera's participation in the
sham transaction. Moreover, Rivera's codefendant Delgado testified
that she and Rivera participated in the transaction. On this
record, we cannot say that the five alleged evidentiary errors
cumulatively "call into doubt the reliability of the verdict and
'the underlying fairness of the trial.'" See United States v.
Sanabria, 645 F.3d 5 05, 519 (1st Cir. 2011) (quoting United States
v. Meserve, 271 F.3d 314 , 332 (1st Cir. 2001)). Therefore, like
his individual allegations of evidentiary error, Rivera's
cumulative-error claim must also fail.
Based on the foregoing, Delgado's convictions are vacated
and her case is remanded for a new trial.
With respect to Rivera's case, for the reasons described
above, his sentence cannot stand in light of the Supreme Court's
decision in Alleyne. We therefore withhold judgment on his
convictions for thirty days, during which time the government can
request either that we affirm Rivera's convictions and remand for
resentencing under 21 U.S.C. § 841(b)(1)(C), or that we vacate
Rivera's convictions and remand for a new trial, allowing the
question of drug quantity to be properly submitted to a jury
applying the beyond-a-reasonable-doubt standard.
Vacated and remanded in part, and judgment withheld in