United States v. Soto-Peguero

18-1897P

2020 | Cited 0 times | First Circuit | October 19, 2020

United States Court of Appeals For the First Circuit

No. 18-1897

UNITED STATES OF AMERICA,

Appellee,

v.

ORISTEL SOTO-PEGUERO,

Defendant, Appellant.

APPEAL FROM THE UNITED STATES DISTRICT COURT FOR THE DISTRICT OF MASSACHUSETTS

[Hon. Rya W. Zobel, U.S. District Judge]

Before

Thompson, Kayatta, and Barron, Circuit Judges.

Jane Elizabeth Lee for appellant. Theodore B. Heinrich, Assistant United States Attorney, with whom Andrew E. Lelling, United States Attorney, was on brief, for appellee.

October 19, 2020

BARRON, Circuit Judge. In April 2018, Oristel Soto-

Peguero was convicted in the District of Massachusetts on three

counts related to distribution of heroin in violation of 21 U.S.C.

§ 841(a)(1) and § 846 and one count of discharging a firearm in

furtherance of a drug crime in violation of 18 U.S.C. § 924(c).

The District Court sentenced him to twenty-two years in prison.

Soto-Peguero now argues on appeal that the District Court erred in

denying his motion to suppress certain evidence at trial. He also

asserts that the District Court should not have concluded that he

was eligible for a two-level role enhancement under the United

States Sentencing Guidelines. He thus asks us to vacate his

convictions and resulting sentence. We affirm.

I.

We begin by summarizing the facts in the record, viewing

them in the light most favorable to the suppression ruling. See

United States v. Arnott, 758 F.3d 40 , 43 (1st Cir. 2014). In

January 2015, a Task Force consisting of agents from the federal

Drug Enforcement Agency ("DEA") and officers from several

Massachusetts law enforcement agencies were engaged in an

investigation of potential heroin suppliers in Taunton,

Massachusetts.1 Pursuant to that joint investigation, between

1 We note that this investigation also led to the indictment of Luis Guzman-Ortiz, whom a separate jury found guilty of conspiring with Soto-Peguero to distribute heroin. Guzman-Ortiz successfully filed a motion for acquittal on that charge pursuant

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January and July 2015, Task Force members used a series of wiretaps

to investigate Eddyberto Mejia-Ramos, a suspected local

trafficker.

The wiretaps intercepted a number of conversations

between Mejia-Ramos and Soto-Peguero, which indicated that Soto-

Peguero was supplying Mejia-Ramos with heroin. Members of the

Task Force suspected that Soto-Peguero's girlfriend, Mercedes

Cabral, sometimes transported the drugs to Mejia-Ramos.

On the afternoon of July 6, 2015, Task Force members

intercepted conversations that indicated that Soto-Peguero would

deliver drugs to Mejia-Ramos's home later that day. Specifically,

just before 9 p.m., Mejia-Ramos called Soto-Peguero and asked him

to come at 10 p.m. and "bring something heavy." Soto-Peguero said

in response that he would "send the woman." Then, at 9:38 p.m.,

he called Mejia-Ramos to let him know "the woman is on her way."

Four minutes earlier, Cabral had left the apartment that

she shared with Soto-Peguero. Several Task Force members followed

her as she drove in the direction of Mejia-Ramos's home. They

then enlisted two Massachusetts State Police troopers to conduct

a traffic stop. The troopers pulled Cabral over and determined

that she was driving on a suspended license. In the process of

to Federal Rule of Criminal Procedure 29. For our opinion affirming the District Court's grant of the Rule 29 motion, see United States v. Guzman-Ortiz, ___ F.3d ___, 2020 WL 5542135 (1st Cir. 2020) [No. 19-1349].

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arresting her, they discovered close to a kilogram of heroin in

her pocketbook.

After Cabral's arrest, Special Agent Carl Rideout, the

DEA agent in charge of the Task Force, directed one of its members

to "freeze" Cabral and Soto-Peguero's residence in order to secure

it while he obtained a search warrant. Task Force members

surrounded the apartment. As they tried to gain entry, someone

fired a gun from inside the apartment out the front door. Task

Force members then managed to enter the premises, without a

warrant, and, while there, found substantial evidence of heroin

possession and trafficking.

The following day, Special Agent Rideout applied for a

search warrant for Soto-Peguero's apartment. The affidavit

supporting the search warrant stated that during a "security sweep"

of the apartment, "officers observed in plain view two large brick

shaped objects believed to be kilograms of heroin, one in each

bedroom." Additionally, the affidavit stated, a Task Force member

"moved one of the bricks" and "observed a firearm beneath it."

The Magistrate Judge granted the warrant application.

Task Force members thereafter executed that search

warrant. In doing so, they discovered additional heroin and other

evidence of drug trafficking.

On March 23, 2016, a grand jury in the United States

District Court for the District of Massachusetts issued a

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superseding eight-count indictment. Soto-Peguero was not named in

Counts One or Four,2 but he was charged with six counts: possession

with intent to distribute 100 grams of heroin in violation of 21

U.S.C. §§ 841(a)(1), 841(b)(1)(B)(i) (Count Two); possession with

intent to distribute one kilogram of heroin in violation of 21

U.S.C. §§ 841(a)(1), 841(b)(1)(A)(i) (Count Three); two counts of

conspiring to distribute and possess heroin in violation of 21

U.S.C. § 846 (Counts Five and Six); illegally possessing a firearm

in violation of 18 U.S.C. § 922(g)(1) (Count Seven); and using a

firearm during and in relation to a drug offense in violation of

18 U.S.C. § 924(c) (Count Eight).

Soto-Peguero moved pursuant to the Fourth Amendment of

the United States Constitution to suppress, among other things,

the evidence that law enforcement had found at his apartment,

including both the drugs and gun discovered without a warrant on

the night Task Force members first entered his home, and the

further evidence that law enforcement uncovered pursuant to the

warrant that was later issued. He contended that, as to the first

batch of evidence, "[n]o exigency justified the police's forced

entry" because even if the Task Force had waited to obtain a

warrant, there would have been no "great likelihood that evidence

2 Count One was brought against Cabral and Count Four was brought against Guzman-Ortiz, who was arrested at the same time as Soto-Peguero.

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would [have] be[en] destroyed." He also asserted that even if the

initial entry had been permissible, "the officers' subsequent

decision to search under the auspices of conducting a 'protective

sweep' [was] unsustainable" because "they had no basis to suspect

another person, let alone a dangerous person, was present." In

addition, Soto-Peguero challenged the contention that the drugs

and gun the Task Force recovered during the warrantless entry were

in "plain view" when law enforcement arrived.

Soto-Peguero separately argued that the search warrant

itself was "defective" because it was "based on evidence that was

illegally obtained" during the course of the warrantless entry

into the apartment. He thus contended that the evidence the Task

Force found after obtaining that warrant had to be suppressed

pursuant to the Fourth Amendment as well.

In reply, the United States argued that exigent

circumstances were present at the time of the initial entry into

the apartment because "[i]t was not unreasonable for DEA officers

to fear that Soto-Peguero might conclude that Cabral had been

arrested when Cabral did not arrive in Taunton, did not return

home, and was unable to communicate with Soto-Peguero." The

government also argued that Soto-Peguero "created a distinct

exigency" when he fired a shot through the front door. Moreover,

the government contended that the scope of the protective sweep

was necessary because "having been fired at, the officers were

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entitled to account for the presence and location of the firearm

to ensure safety" and pointed out that Task Force members had

"testified [at the grand jury] that the heroin package in the front

bedroom was in plain view."

Finally, the government contended that, even if the Task

Force members' conduct exceeded that of an appropriate protective

sweep, the exclusionary rule should not apply. The government

argued there was "no doubt but that agents would have sought and

obtained [a warrant] whether or not they observed the kilograms of

heroin in [the] apartment during the sweep," and therefore that

the evidence "inevitably would have been revealed in some other

lawful way." For that proposition, the government relied on the

inevitable discovery doctrine, which provides that evidence

obtained in violation of the Fourth Amendment is admissible "if it

ineluctably would have been revealed in some other (lawful) way, so

long as (i) the lawful means of its discovery are independent and

would necessarily have been employed, (ii) discovery by that means

is in fact inevitable, and (iii) application of the doctrine in a

particular case will not sully the prophylaxis of the Fourth

Amendment." United States v. Zapata, 18 F.3d 971 , 978 (1st Cir.

1994) (internal citations omitted).

Soto-Peguero responded in a separate memorandum,

arguing, among other things, that applying the inevitable

discovery doctrine in this case would, in fact, "sully the

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prophylaxis of the Fourth Amendment." He contended that admitting

the evidence would incentivize police misconduct because it would

"assure[] police that they need not wait for a magistrate's

approval." He argued that this is "what happened here" because

the officers "had little concern about prematurely prying open a

heating vent and rifling through a closed nightstand" since they

were confident a warrant would later issue.

The District Court held a hearing on Soto-Peguero's

motion to suppress and heard testimony from both Soto-Peguero and

Task Force members who were involved in the warrantless entry and

the execution of the search warrant. The focus of that evidentiary

hearing was on the Task Force members' and the defendant's

conflicting accounts regarding what transpired during the

warrantless entry of Soto-Peguero's home. There were three salient

points of disagreement: whether the heroin that law enforcement

found in the front bedroom during the initial entry into the

apartment had been in plain view or was concealed by the cover of

an air vent; whether the heroin found in a black plastic bag in

the rear bedroom that same night had been between the bed and the

nightstand or in a drawer of the nightstand; and whether Special

Agent Meletis, of the DEA, looked inside the black plastic bag

during the warrantless entry, as he testified in the suppression

hearing, or only the next day after having obtained the search

warrant, as he testified before the grand jury in March of 2016.

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Soto-Peguero also testified at the hearing that, while he was

detained on the first floor of his apartment, it sounded "[l]ike

they were breaking stuff" upstairs and that his bed frame had been

intact prior to the search.

Soto-Peguero and the United States then both filed post-

hearing briefs. As relevant here, in addition to renewing the

objections from his motion to suppress, Soto-Peguero elaborated on

his assertion that the District Court "should not excuse the

officers' misconduct by applying the inevitable discovery rule."

In support of that contention, he pointed to what he characterized

as "[t]he fact that at least one officer testified inconsistently

about the scope of his search -- denying and then admitting that

he looked inside a black bag" and to what he contended was the

fact that the "officers[] unreasonabl[y] delay[ed] in seeking the

search warrant" because "they anticipated entering his home that

day," but "rather than bothering to apply for judicial

authorization, they sent more than ten officers to prepare to

'secure' the apartment without a warrant."

In its post-hearing filing, the United States contended

that the inevitable discovery doctrine's requirements were met.

First, the government repeated its contention that "there can be

no doubt but that agents would have sought and obtained [a search

warrant] whether or not they observed the kilograms of heroin in

[the] apartment during the sweep." The United States also

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reiterated that there was "no reason to discredit the testimony of

the officers" who averred that the heroin in the front bedroom was

in plain view. The government then further contended -- in an

argument that appeared to invoke the distinct exception to the

exclusionary rule known as the independent source doctrine, see

Murray v. United States, 487 U.S. 533 , 537 (1988) -- that even "if

the discovery of the heroin and firearm [were] excised from the

affidavit in support of the search warrant, there [was] still

overwhelming probable cause to justify the issuance of the

warrant."

The District Court denied Soto-Peguero's motion to

suppress. United States v. Soto-Peguero, 252 F. Supp. 3d 1 , 14

(D. Mass. 2017). First, the District Court found that exigent

circumstances justified the initial warrantless entry. Id. at 11-

12. The District Court concluded that if Cabral had failed to

return in a timely manner, and if Soto-Peguero had been unable to

reach her, he might have concluded that law enforcement was

"closing in" on him. Id.

The District Court also found that it was reasonable for

the Task Force members to delay in obtaining the warrant, even if

they had probable cause to search the apartment before Cabral

departed with some of the drugs. Id. at 12. Under Supreme Court

precedent, the District Court reasoned, there are "many entirely

proper reasons why police may not want to seek a search warrant as

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soon as the bare minimum of evidence needed to establish probable

cause is acquired." Id. (quoting Kentucky v. King, 563 U.S. 452 ,

466-67 (2011)). And, the District Court further determined, the

fact that "police might have foreseen the eventual entry" was not

enough on its own to "prevent application of the exigent

circumstances doctrine." Id. (quoting United States v. Samboy,

433 F.3d 154 , 160 (1st Cir. 2005)).

The District Court next explained, however, that it was

"not persuaded by the officers' account that a block of heroin was

sticking out of a floor vent." Id. at 13. The District Court

also declined to "resolve the conflicting evidence as to whether

a bag in the back bedroom containing heroin was in a drawer or

next to the bed." Id. "[E]ven accepting the government's version

of events as true," the court held that "manipulating an object in

a vent and opening a bag goes beyond the scope of a protective

sweep." Id.

Nevertheless, the District Court denied Soto-Peguero's

motion to suppress under the inevitable discovery exception to the

exclusionary rule. The District Court concluded that, even if the

Task Force members had not found the heroin or the gun in their

warrantless search of Soto-Peguero's home, they would have found

that evidence after obtaining a search warrant. The District Court

credited Special Agent Rideout's testimony that he would have

pursued a warrant even if no evidence had been uncovered during

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the "protective sweep." Id. And the District Court concluded

that the Task Force had probable cause to support a warrant for

such a search even before a single member entered the apartment.

Id. Therefore, according to the District Court, the government

had "demonstrate[d], to a high degree of probability," that the

evidence inevitably would have been discovered. Id. (alteration

in original) (quoting United States v. Almeida, 434 F.3d 25 , 29

(1st Cir. 2006)).

The District Court did express disapproval of the fact

that Task Force members looked inside the vent and the bag. But,

it went on to conclude that admitting the evidence was "unlikely

to 'erode [Fourth Amendment] protections or encourage police

misconduct.'" Id. at 14 (alteration in original) (quoting Almeida,

434 F.3d at 29 ). Thus, it determined that admitting the evidence

would not "sully the prophylaxis of the Fourth Amendment" and

therefore "the deterrence rationale [did] not justify putting the

police in a worse position than they would have been had no

misconduct occurred." Id. at 13-14 (first quoting Zapata, 18 F.3d

at 978 ; then quoting United States v. Silvestri, 787 F.2d 736 , 740

(1st Cir. 1986)). The District Court therefore denied Soto-

Peguero's suppression motion.

The case proceeded to trial, which lasted six days. On

April 2, 2018, the jury convicted Soto-Peguero on Counts Two,

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Three, Five, and Eight of the indictment, but acquitted him on

Count Six (conspiring with Guzman-Ortiz).3

For the purposes of calculating Soto-Peguero's

sentencing range under the Guidelines, the Presentence

Investigation Report ("PSR") that the United States Office of

Probation prepared grouped the first three counts of conviction

(Counts Two, Three, and Five) separately from the firearm

conviction (Count Eight). The PSR determined that, based on the

quantity of heroin discovered, Soto-Peguero's base offense level

should be set at 32 for the three grouped charges. The PSR also

applied a two-level role enhancement under § 3B1.1(c) of the

Guidelines, because Soto-Peguero "directed his significant other

at the time, Mercedes Cabral, to deliver drugs for him on at least

four separate occasions."

Soto-Peguero objected to the role enhancement both in

his sentencing memorandum and at the sentencing hearing. The

United States argued that Cabral was "clearly directed by Mr. Soto-

Peguero" and that it was "very plain that Mr. Soto-Peguero was

supervising" her activities. The District Court agreed that Soto-

Peguero was "much more the head of the enterprise" than Cabral was

and upheld the role enhancement accordingly.

3 Count Seven was dismissed prior to trial.

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Including the role enhancement, and accounting for the

extent of Soto-Peguero's criminal record, the mandatory 10-year

prison sentence for his firearm charge, and his history of mental

health struggles and childhood abuse, the District Court sentenced

him to a total term of incarceration of 264 months with a five-

year term of supervised release and a $400 special assessment.

The District Court entered judgment on September 12, 2018.

On September 18, 2018, Soto-Peguero filed a timely notice of

appeal. We have jurisdiction over his appeal from his conviction

under 28 U.S.C. § 1291. We have jurisdiction over his appeal from

his sentence under 18 U.S.C. § 3742(a).

II.

When a district court denies a motion to suppress, we

review the legal questions de novo and evaluate the factfinding

for clear error. United States v. Ackies, 918 F.3d 190 , 197 (1st

Cir. 2019).

A.

Soto-Peguero first asserts that the Fourth Amendment

requires suppression of both the evidence the Task Force found the

night of the warrantless entry and the evidence uncovered the

following day pursuant to the search warrant. He contends that

"[t]here was no information [in the warrant application], aside

from the illegally obtained evidence, supporting a finding that

enumerated evidence of contraband or of a crime would be found" at

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his home. Failing that, he argues that, at the very least, the

"closeness" of the question of whether probable cause existed

without the illegally obtained evidence "makes it impossible to

conclude . . . that the Magistrate's decision to issue the warrant

was unaffected by the illegal evidence."

But, Soto-Peguero's focus on the warrant application is

misplaced. The District Court held that the evidence at issue --

both the evidence discovered during the warrantless entry and the

evidence found the following day -- is admissible under the

inevitable discovery doctrine. Under that exception to the

exclusionary rule, "[i]f the prosecution can establish by a

preponderance of the evidence that the information ultimately or

inevitably would have been discovered by lawful means . . . the

evidence should be received." Nix v. Williams, 467 U.S. 431 , 444

(1984). In this case, that means the government must establish

that, had there been no search in violation of the Fourth

Amendment, the officers inevitably would have applied for a

warrant, obtained it, and discovered the evidence in question when

executing that warrant. See United States v. Procopio, 88 F.3d

21 , 27 (1st Cir. 1996) (applying the inevitable discovery doctrine

to admit the illegally uncovered contents of a briefcase where

there was "little reason to doubt that the local police would have

contacted federal agents, even without the information gleaned

during the search," and where it was "even more certain that

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federal agents . . . would have then sought a warrant to search

the briefcase"). Thus, because the Task Force members need not

have actually obtained a warrant to rely on the inevitable

discovery exception, any defects in the warrant that they did

obtain the day after their initial warrantless entry of Soto-

Peguero's apartment are not directly relevant to the question of

whether the evidence at issue must be suppressed. See Silvestri,

787 F.2d at 744 (contemplating situations where a warrantless

search is never followed by a warrant and yet the government relies

on the inevitable discovery doctrine).

Moreover, here, the United States has made the required

showing under the inevitable discovery doctrine. In that regard,

Soto-Peguero does not challenge Special Agent Rideout's testimony

that he would have pursued a warrant regardless of what was found

in securing the apartment. He also does not argue that, if the

Task Force members had delayed entry until they obtained a valid

search warrant, they would not have found the evidence in question

upon its execution.

To the extent that we can read Soto-Peguero's claim that

the warrant application would have been insufficient without the

illegally obtained evidence as an argument that the police did not

have probable cause to search his home before they entered it, we

disagree. Soto-Peguero and Cabral lived together at the searched

location; he spoke to Mejia-Ramos on July 6, indicating that he

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would deliver heroin that day; he told Mejia-Ramos that Cabral was

on her way around 9:38 p.m., four minutes after she had left their

apartment; and Cabral was then stopped with close to a kilogram of

heroin in her pocketbook. We thus agree with the District Court

that "the officers had sufficient probable cause" to substantiate

a search warrant for Soto-Peguero's apartment before the

protective sweep even began. Soto-Peguero, 252 F. Supp. 3d at 13 .

B.

Soto-Peguero separately argues that the District Court

erred in insulating the evidence at issue from the exclusionary

rule by adverting to our precedent that, in analyzing whether to

admit evidence through the inevitable discovery doctrine, we must

also consider whether doing so would "encourage police misconduct"

and thereby "sully the prophylaxis of the Fourth Amendment."

United States v. Hughes, 640 F.3d 428 , 440-41 (1st Cir. 2011)

(quoting Zapata, 18 F.3d at 978 ). In undertaking that inquiry, we

need to "dwell[] closely on the facts" and look toward whether the

record establishes that law enforcement officers intentionally

violated the Fourth Amendment as well as the incentives, if any,

for them to act unconstitutionally. United States v. Scott, 270

F.3d 30 , 45 (1st Cir. 2001); see also Hughes, 640 F.3d at 441 .

But, rather than develop an argument along those precise lines,

Soto-Peguero instead directs our attention to an out-of-circuit

case, United States v. Madrid, 152 F.3d 1034 (8th Cir. 1998).

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There, the Eighth Circuit recognized an exception to the inevitable

discovery doctrine because police behaved egregiously and

"exploited their presence" in the defendant's home. Id. at 1040. Either way, Soto-Peguero's attempt to make the case that the

conduct by law enforcement here precludes us from affirming the

District Court's inevitable discovery ruling fails.

Invoking Madrid, Soto-Peguero cites to a number of

instances of purported misconduct that he argues necessitate

suppression even if the inevitable discovery exception otherwise

would apply. Specifically, he alleges that the Task Force members

"tore the residence apart," "destroy[ed] furniture," "open[ed]

drawers," "open[ed] containers," "pr[ied] the lid off [an] air

conditioning vent," and "used this illegally obtained evidence to

secure the warrant" during their first entry to his apartment. He

also contends that admitting this evidence would "make[] the court

complicit in the officers' false testimony at the suppression

hearing."

Soto-Peguero makes the allegation that Task Force

members "tore the residence apart" and "destroy[ed] furniture" in

support of his Madrid-based argument for the first time on appeal.

Thus, our review of it is at most for plain error. See United

States v. Lara, 970 F.3d 68 , 76 (1st Cir. 2020). We find none, as

the District Court was not asked to make a finding about what, if

any, damage the Task Force members caused in going through the

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apartment during their initial entry and the District Court did

not do so on its own. See United States v. Takesian, 945 F.3d

553 , 563 (1st Cir. 2019) (explaining that "if an error pressed by

the appellant turns on 'a factual finding [he] neglected to ask

the district court to make, the error cannot be clear or obvious

unless' he shows that 'the desired factual finding is the only one

rationally supported by the record below'" (quoting United States

v. Olivier-Diaz, 13 F.3d 1 , 5 (1st Cir. 1993))).

We turn, then, to the aspects of Soto-Peguero's Madrid-

based argument that rely on the remaining allegations of

misconduct. In part, Soto-Peguero relies on the assertion that

the record evidence indicates that Task Force members opened the

drawer of the nightstand and looked inside the floor vent when

they went through the apartment without a warrant. But, even

accepting that the evidence supports that understanding of their

conduct, it still "falls short of the blatant search through

personal effects in Madrid," just as we concluded the last time

that a criminal defendant asked us to follow the Eighth Circuit's

lead. United States v. Dent, 867 F.3d 37 , 41 (1st Cir. 2017); see

id. (holding that when an officer exceeded the scope of a

protective sweep by looking under an air mattress, that did not

bring the case within Madrid's purview).

So, that leaves only Soto-Peguero's contentions that the

inclusion of a description of the evidence turned up during the

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warrantless entry in the warrant affidavit and "the officers' false

testimony" at the suppression hearing satisfy the Madrid standard,

at least when considered in the context of how the officers

conducted themselves at that time. We assume, for the sake of

argument only, that the Eighth Circuit's holding that the officers

in Madrid "exploited their presence" in the defendant's home

extends to encompass this flavor of alleged misconduct. Even

still, here, too, we are not persuaded.

The affidavit attached to the search warrant application

did describe evidence that Task Force members uncovered pursuant

to what that affidavit characterized as a "security sweep." And,

as Soto-Peguero notes, the District Court later found that some of

that evidence was obtained through methods that exceeded the scope

of such a sweep. But, we do not see how this mismatch suffices to

support Soto-Peguero's Madrid-based suppression argument. The

Task Force members had been shot at as they tried to enter the

residence and would later testify that they found the evidence

while trying to secure the apartment and locate the firearm in

question. In such circumstances, we cannot say that the warrant

application's erroneous description of the means by which that

evidence had been acquired constitutes the kind of egregious

conduct that, per Madrid, could justify suppression. Cf. United

States v. Paradis, 351 F.3d 21 , 29 n.7 (1st Cir. 2003) (describing

scenarios in which a protective sweep might properly authorize an

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officer to specifically search for weapons). Consistent with this

conclusion, we note that the District Court made no finding here

that any law enforcement officer involved in the preparation of

the warrant application either knowingly included

unconstitutionally obtained evidence or knowingly misdescribed

that evidence as having been lawfully obtained.

With respect to Soto-Peguero's contention that Madrid

requires suppression here based on his allegation that Task Force

members gave false testimony at the suppression hearing, we are

likewise unpersuaded. The District Court did explain that it was

not fully persuaded by the Task Force members' testimony at the

suppression hearing regarding what happened during the warrantless

entry. But, the District Court also concluded that there was no

basis for finding on this record the kind of egregious or flagrant

official misconduct that would require suppression in order to not

sully the prophylaxis of the Fourth Amendment. Soto-Peguero, 252

F. Supp. 3d at 13 -14. In the face of that ruling and the absence

of any finding by the District Court that the Task Force members

who testified at that hearing did so in bad faith, we see no basis

for requiring suppression even were we to accept Soto-Peguero's

argument that we should adopt the Madrid standard.

Because Soto-Peguero has not succeeded in establishing

that the United States failed to meet the requirements for applying

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the inevitable discovery doctrine, we affirm the District Court's

denial of his motion to suppress.

III.

Soto-Peguero also challenges the fact that the Probation

Office applied a two-level role enhancement to increase the

Guidelines range for his drug possession-related crimes from 168-

210 months to 210-262 months.

Under § 3B1.1(c) of the Guidelines, a defendant's

offense level is increased by two levels if "the defendant was an

organizer, leader, manager, or supervisor in any criminal

activity" involving four or fewer participants. For the

enhancement to apply, the government bears the burden of proving,

by a preponderance of the evidence, that "the criminal enterprise

involved at least two complicit participants (of whom the defendant

may be counted as one)" and that "the defendant, in committing the

offense, exercised control over, organized, or was otherwise

responsible for superintending the activities of, at least one of

those other persons." United States v. Cruz, 120 F.3d 1 , 3 (1st

Cir. 1997). "The determination of an individual's role in

committing an offense is necessarily fact-specific. Accordingly,

appellate review must be conducted with considerable deference."

Id. (internal citation omitted). Even a single instance of

managing the actions of others can substantiate the enhancement.

See United States v. Voccola, 99 F.3d 37 , 44 (1st Cir. 1996).

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Soto-Peguero argues that the entirety of the

government's case for the enhancement is that, on two occasions,

he stated that he was "sending" Cabral. He asserts that, beyond

that, there is nothing in the record to support the conclusion

that he and Cabral "were anything other than equal participants in

criminal activity."

The United States points out that Soto-Peguero had

"scores of communications" with Mejia-Ramos, while Cabral only

interacted with him to ask to which house she should go. On one

occasion, Mejia-Ramos contacted Soto-Peguero and told him the

heroin was poor quality. Soto-Peguero replied: "My woman is on

the way." Later, Cabral retrieved what were presumably the

inferior drugs from Mejia-Ramos's cousin. On another occasion,

after Cabral dropped off a package, Mejia-Ramos called Soto-

Peguero to ask what he had sent. Per the government's

characterization, "both Mejia-Ramos and his cousin treated Cabral

as a mere delivery person and engaged only Soto-Peguero in

important business decisions."

At sentencing, the District Court -- after presiding

over a six-day trial and observing both Soto-Peguero and Cabral

-- concluded that "Soto-Peguero was running the show." He "told

[Cabral] to go to Brockton or wherever it was on a number of

occasions." That was where she "ultimately got caught."

- 23 -

Based on all the evidence cited by the United States,

and accounting for the fact that the District Court had the

opportunity to observe the witnesses and the defendant firsthand,

we cannot conclude that the District Court clearly erred in holding

that the government had shown by a preponderance of the evidence

that Soto-Peguero was managing or supervising Cabral on at least

one occasion. We therefore affirm the District Court's decision.

IV.

As described above, we affirm both Soto-Peguero's

convictions and his sentence.

- 24 -

United States Court of Appeals For the First Circuit

No. 18-1897

UNITED STATES OF AMERICA,

Appellee,

v.

ORISTEL SOTO-PEGUERO,

Defendant, Appellant.

APPEAL FROM THE UNITED STATES DISTRICT COURT FOR THE DISTRICT OF MASSACHUSETTS

[Hon. Rya W. Zobel, U.S. District Judge]

Before

Thompson, Kayatta, and Barron, Circuit Judges.

Jane Elizabeth Lee for appellant. Theodore B. Heinrich, Assistant United States Attorney, with whom Andrew E. Lelling, United States Attorney, was on brief, for appellee.

October 19, 2020

BARRON, Circuit Judge. In April 2018, Oristel Soto-

Peguero was convicted in the District of Massachusetts on three

counts related to distribution of heroin in violation of 21 U.S.C.

§ 841(a)(1) and § 846 and one count of discharging a firearm in

furtherance of a drug crime in violation of 18 U.S.C. § 924(c).

The District Court sentenced him to twenty-two years in prison.

Soto-Peguero now argues on appeal that the District Court erred in

denying his motion to suppress certain evidence at trial. He also

asserts that the District Court should not have concluded that he

was eligible for a two-level role enhancement under the United

States Sentencing Guidelines. He thus asks us to vacate his

convictions and resulting sentence. We affirm.

I.

We begin by summarizing the facts in the record, viewing

them in the light most favorable to the suppression ruling. See

United States v. Arnott, 758 F.3d 40 , 43 (1st Cir. 2014). In

January 2015, a Task Force consisting of agents from the federal

Drug Enforcement Agency ("DEA") and officers from several

Massachusetts law enforcement agencies were engaged in an

investigation of potential heroin suppliers in Taunton,

Massachusetts.1 Pursuant to that joint investigation, between

1 We note that this investigation also led to the indictment of Luis Guzman-Ortiz, whom a separate jury found guilty of conspiring with Soto-Peguero to distribute heroin. Guzman-Ortiz successfully filed a motion for acquittal on that charge pursuant

- 2 -

January and July 2015, Task Force members used a series of wiretaps

to investigate Eddyberto Mejia-Ramos, a suspected local

trafficker.

The wiretaps intercepted a number of conversations

between Mejia-Ramos and Soto-Peguero, which indicated that Soto-

Peguero was supplying Mejia-Ramos with heroin. Members of the

Task Force suspected that Soto-Peguero's girlfriend, Mercedes

Cabral, sometimes transported the drugs to Mejia-Ramos.

On the afternoon of July 6, 2015, Task Force members

intercepted conversations that indicated that Soto-Peguero would

deliver drugs to Mejia-Ramos's home later that day. Specifically,

just before 9 p.m., Mejia-Ramos called Soto-Peguero and asked him

to come at 10 p.m. and "bring something heavy." Soto-Peguero said

in response that he would "send the woman." Then, at 9:38 p.m.,

he called Mejia-Ramos to let him know "the woman is on her way."

Four minutes earlier, Cabral had left the apartment that

she shared with Soto-Peguero. Several Task Force members followed

her as she drove in the direction of Mejia-Ramos's home. They

then enlisted two Massachusetts State Police troopers to conduct

a traffic stop. The troopers pulled Cabral over and determined

that she was driving on a suspended license. In the process of

to Federal Rule of Criminal Procedure 29. For our opinion affirming the District Court's grant of the Rule 29 motion, see United States v. Guzman-Ortiz, ___ F.3d ___, 2020 WL 5542135 (1st Cir. 2020) [No. 19-1349].

- 3 -

arresting her, they discovered close to a kilogram of heroin in

her pocketbook.

After Cabral's arrest, Special Agent Carl Rideout, the

DEA agent in charge of the Task Force, directed one of its members

to "freeze" Cabral and Soto-Peguero's residence in order to secure

it while he obtained a search warrant. Task Force members

surrounded the apartment. As they tried to gain entry, someone

fired a gun from inside the apartment out the front door. Task

Force members then managed to enter the premises, without a

warrant, and, while there, found substantial evidence of heroin

possession and trafficking.

The following day, Special Agent Rideout applied for a

search warrant for Soto-Peguero's apartment. The affidavit

supporting the search warrant stated that during a "security sweep"

of the apartment, "officers observed in plain view two large brick

shaped objects believed to be kilograms of heroin, one in each

bedroom." Additionally, the affidavit stated, a Task Force member

"moved one of the bricks" and "observed a firearm beneath it."

The Magistrate Judge granted the warrant application.

Task Force members thereafter executed that search

warrant. In doing so, they discovered additional heroin and other

evidence of drug trafficking.

On March 23, 2016, a grand jury in the United States

District Court for the District of Massachusetts issued a

- 4 -

superseding eight-count indictment. Soto-Peguero was not named in

Counts One or Four,2 but he was charged with six counts: possession

with intent to distribute 100 grams of heroin in violation of 21

U.S.C. §§ 841(a)(1), 841(b)(1)(B)(i) (Count Two); possession with

intent to distribute one kilogram of heroin in violation of 21

U.S.C. §§ 841(a)(1), 841(b)(1)(A)(i) (Count Three); two counts of

conspiring to distribute and possess heroin in violation of 21

U.S.C. § 846 (Counts Five and Six); illegally possessing a firearm

in violation of 18 U.S.C. § 922(g)(1) (Count Seven); and using a

firearm during and in relation to a drug offense in violation of

18 U.S.C. § 924(c) (Count Eight).

Soto-Peguero moved pursuant to the Fourth Amendment of

the United States Constitution to suppress, among other things,

the evidence that law enforcement had found at his apartment,

including both the drugs and gun discovered without a warrant on

the night Task Force members first entered his home, and the

further evidence that law enforcement uncovered pursuant to the

warrant that was later issued. He contended that, as to the first

batch of evidence, "[n]o exigency justified the police's forced

entry" because even if the Task Force had waited to obtain a

warrant, there would have been no "great likelihood that evidence

2 Count One was brought against Cabral and Count Four was brought against Guzman-Ortiz, who was arrested at the same time as Soto-Peguero.

- 5 -

would [have] be[en] destroyed." He also asserted that even if the

initial entry had been permissible, "the officers' subsequent

decision to search under the auspices of conducting a 'protective

sweep' [was] unsustainable" because "they had no basis to suspect

another person, let alone a dangerous person, was present." In

addition, Soto-Peguero challenged the contention that the drugs

and gun the Task Force recovered during the warrantless entry were

in "plain view" when law enforcement arrived.

Soto-Peguero separately argued that the search warrant

itself was "defective" because it was "based on evidence that was

illegally obtained" during the course of the warrantless entry

into the apartment. He thus contended that the evidence the Task

Force found after obtaining that warrant had to be suppressed

pursuant to the Fourth Amendment as well.

In reply, the United States argued that exigent

circumstances were present at the time of the initial entry into

the apartment because "[i]t was not unreasonable for DEA officers

to fear that Soto-Peguero might conclude that Cabral had been

arrested when Cabral did not arrive in Taunton, did not return

home, and was unable to communicate with Soto-Peguero." The

government also argued that Soto-Peguero "created a distinct

exigency" when he fired a shot through the front door. Moreover,

the government contended that the scope of the protective sweep

was necessary because "having been fired at, the officers were

- 6 -

entitled to account for the presence and location of the firearm

to ensure safety" and pointed out that Task Force members had

"testified [at the grand jury] that the heroin package in the front

bedroom was in plain view."

Finally, the government contended that, even if the Task

Force members' conduct exceeded that of an appropriate protective

sweep, the exclusionary rule should not apply. The government

argued there was "no doubt but that agents would have sought and

obtained [a warrant] whether or not they observed the kilograms of

heroin in [the] apartment during the sweep," and therefore that

the evidence "inevitably would have been revealed in some other

lawful way." For that proposition, the government relied on the

inevitable discovery doctrine, which provides that evidence

obtained in violation of the Fourth Amendment is admissible "if it

ineluctably would have been revealed in some other (lawful) way, so

long as (i) the lawful means of its discovery are independent and

would necessarily have been employed, (ii) discovery by that means

is in fact inevitable, and (iii) application of the doctrine in a

particular case will not sully the prophylaxis of the Fourth

Amendment." United States v. Zapata, 18 F.3d 971 , 978 (1st Cir.

1994) (internal citations omitted).

Soto-Peguero responded in a separate memorandum,

arguing, among other things, that applying the inevitable

discovery doctrine in this case would, in fact, "sully the

- 7 -

prophylaxis of the Fourth Amendment." He contended that admitting

the evidence would incentivize police misconduct because it would

"assure[] police that they need not wait for a magistrate's

approval." He argued that this is "what happened here" because

the officers "had little concern about prematurely prying open a

heating vent and rifling through a closed nightstand" since they

were confident a warrant would later issue.

The District Court held a hearing on Soto-Peguero's

motion to suppress and heard testimony from both Soto-Peguero and

Task Force members who were involved in the warrantless entry and

the execution of the search warrant. The focus of that evidentiary

hearing was on the Task Force members' and the defendant's

conflicting accounts regarding what transpired during the

warrantless entry of Soto-Peguero's home. There were three salient

points of disagreement: whether the heroin that law enforcement

found in the front bedroom during the initial entry into the

apartment had been in plain view or was concealed by the cover of

an air vent; whether the heroin found in a black plastic bag in

the rear bedroom that same night had been between the bed and the

nightstand or in a drawer of the nightstand; and whether Special

Agent Meletis, of the DEA, looked inside the black plastic bag

during the warrantless entry, as he testified in the suppression

hearing, or only the next day after having obtained the search

warrant, as he testified before the grand jury in March of 2016.

- 8 -

Soto-Peguero also testified at the hearing that, while he was

detained on the first floor of his apartment, it sounded "[l]ike

they were breaking stuff" upstairs and that his bed frame had been

intact prior to the search.

Soto-Peguero and the United States then both filed post-

hearing briefs. As relevant here, in addition to renewing the

objections from his motion to suppress, Soto-Peguero elaborated on

his assertion that the District Court "should not excuse the

officers' misconduct by applying the inevitable discovery rule."

In support of that contention, he pointed to what he characterized

as "[t]he fact that at least one officer testified inconsistently

about the scope of his search -- denying and then admitting that

he looked inside a black bag" and to what he contended was the

fact that the "officers[] unreasonabl[y] delay[ed] in seeking the

search warrant" because "they anticipated entering his home that

day," but "rather than bothering to apply for judicial

authorization, they sent more than ten officers to prepare to

'secure' the apartment without a warrant."

In its post-hearing filing, the United States contended

that the inevitable discovery doctrine's requirements were met.

First, the government repeated its contention that "there can be

no doubt but that agents would have sought and obtained [a search

warrant] whether or not they observed the kilograms of heroin in

[the] apartment during the sweep." The United States also

- 9 -

reiterated that there was "no reason to discredit the testimony of

the officers" who averred that the heroin in the front bedroom was

in plain view. The government then further contended -- in an

argument that appeared to invoke the distinct exception to the

exclusionary rule known as the independent source doctrine, see

Murray v. United States, 487 U.S. 533 , 537 (1988) -- that even "if

the discovery of the heroin and firearm [were] excised from the

affidavit in support of the search warrant, there [was] still

overwhelming probable cause to justify the issuance of the

warrant."

The District Court denied Soto-Peguero's motion to

suppress. United States v. Soto-Peguero, 252 F. Supp. 3d 1 , 14

(D. Mass. 2017). First, the District Court found that exigent

circumstances justified the initial warrantless entry. Id. at 11-

12. The District Court concluded that if Cabral had failed to

return in a timely manner, and if Soto-Peguero had been unable to

reach her, he might have concluded that law enforcement was

"closing in" on him. Id.

The District Court also found that it was reasonable for

the Task Force members to delay in obtaining the warrant, even if

they had probable cause to search the apartment before Cabral

departed with some of the drugs. Id. at 12. Under Supreme Court

precedent, the District Court reasoned, there are "many entirely

proper reasons why police may not want to seek a search warrant as

- 10 -

soon as the bare minimum of evidence needed to establish probable

cause is acquired." Id. (quoting Kentucky v. King, 563 U.S. 452 ,

466-67 (2011)). And, the District Court further determined, the

fact that "police might have foreseen the eventual entry" was not

enough on its own to "prevent application of the exigent

circumstances doctrine." Id. (quoting United States v. Samboy,

433 F.3d 154 , 160 (1st Cir. 2005)).

The District Court next explained, however, that it was

"not persuaded by the officers' account that a block of heroin was

sticking out of a floor vent." Id. at 13. The District Court

also declined to "resolve the conflicting evidence as to whether

a bag in the back bedroom containing heroin was in a drawer or

next to the bed." Id. "[E]ven accepting the government's version

of events as true," the court held that "manipulating an object in

a vent and opening a bag goes beyond the scope of a protective

sweep." Id.

Nevertheless, the District Court denied Soto-Peguero's

motion to suppress under the inevitable discovery exception to the

exclusionary rule. The District Court concluded that, even if the

Task Force members had not found the heroin or the gun in their

warrantless search of Soto-Peguero's home, they would have found

that evidence after obtaining a search warrant. The District Court

credited Special Agent Rideout's testimony that he would have

pursued a warrant even if no evidence had been uncovered during

- 11 -

the "protective sweep." Id. And the District Court concluded

that the Task Force had probable cause to support a warrant for

such a search even before a single member entered the apartment.

Id. Therefore, according to the District Court, the government

had "demonstrate[d], to a high degree of probability," that the

evidence inevitably would have been discovered. Id. (alteration

in original) (quoting United States v. Almeida, 434 F.3d 25 , 29

(1st Cir. 2006)).

The District Court did express disapproval of the fact

that Task Force members looked inside the vent and the bag. But,

it went on to conclude that admitting the evidence was "unlikely

to 'erode [Fourth Amendment] protections or encourage police

misconduct.'" Id. at 14 (alteration in original) (quoting Almeida,

434 F.3d at 29 ). Thus, it determined that admitting the evidence

would not "sully the prophylaxis of the Fourth Amendment" and

therefore "the deterrence rationale [did] not justify putting the

police in a worse position than they would have been had no

misconduct occurred." Id. at 13-14 (first quoting Zapata, 18 F.3d

at 978 ; then quoting United States v. Silvestri, 787 F.2d 736 , 740

(1st Cir. 1986)). The District Court therefore denied Soto-

Peguero's suppression motion.

The case proceeded to trial, which lasted six days. On

April 2, 2018, the jury convicted Soto-Peguero on Counts Two,

- 12 -

Three, Five, and Eight of the indictment, but acquitted him on

Count Six (conspiring with Guzman-Ortiz).3

For the purposes of calculating Soto-Peguero's

sentencing range under the Guidelines, the Presentence

Investigation Report ("PSR") that the United States Office of

Probation prepared grouped the first three counts of conviction

(Counts Two, Three, and Five) separately from the firearm

conviction (Count Eight). The PSR determined that, based on the

quantity of heroin discovered, Soto-Peguero's base offense level

should be set at 32 for the three grouped charges. The PSR also

applied a two-level role enhancement under § 3B1.1(c) of the

Guidelines, because Soto-Peguero "directed his significant other

at the time, Mercedes Cabral, to deliver drugs for him on at least

four separate occasions."

Soto-Peguero objected to the role enhancement both in

his sentencing memorandum and at the sentencing hearing. The

United States argued that Cabral was "clearly directed by Mr. Soto-

Peguero" and that it was "very plain that Mr. Soto-Peguero was

supervising" her activities. The District Court agreed that Soto-

Peguero was "much more the head of the enterprise" than Cabral was

and upheld the role enhancement accordingly.

3 Count Seven was dismissed prior to trial.

- 13 -

Including the role enhancement, and accounting for the

extent of Soto-Peguero's criminal record, the mandatory 10-year

prison sentence for his firearm charge, and his history of mental

health struggles and childhood abuse, the District Court sentenced

him to a total term of incarceration of 264 months with a five-

year term of supervised release and a $400 special assessment.

The District Court entered judgment on September 12, 2018.

On September 18, 2018, Soto-Peguero filed a timely notice of

appeal. We have jurisdiction over his appeal from his conviction

under 28 U.S.C. § 1291. We have jurisdiction over his appeal from

his sentence under 18 U.S.C. § 3742(a).

II.

When a district court denies a motion to suppress, we

review the legal questions de novo and evaluate the factfinding

for clear error. United States v. Ackies, 918 F.3d 190 , 197 (1st

Cir. 2019).

A.

Soto-Peguero first asserts that the Fourth Amendment

requires suppression of both the evidence the Task Force found the

night of the warrantless entry and the evidence uncovered the

following day pursuant to the search warrant. He contends that

"[t]here was no information [in the warrant application], aside

from the illegally obtained evidence, supporting a finding that

enumerated evidence of contraband or of a crime would be found" at

- 14 -

his home. Failing that, he argues that, at the very least, the

"closeness" of the question of whether probable cause existed

without the illegally obtained evidence "makes it impossible to

conclude . . . that the Magistrate's decision to issue the warrant

was unaffected by the illegal evidence."

But, Soto-Peguero's focus on the warrant application is

misplaced. The District Court held that the evidence at issue --

both the evidence discovered during the warrantless entry and the

evidence found the following day -- is admissible under the

inevitable discovery doctrine. Under that exception to the

exclusionary rule, "[i]f the prosecution can establish by a

preponderance of the evidence that the information ultimately or

inevitably would have been discovered by lawful means . . . the

evidence should be received." Nix v. Williams, 467 U.S. 431 , 444

(1984). In this case, that means the government must establish

that, had there been no search in violation of the Fourth

Amendment, the officers inevitably would have applied for a

warrant, obtained it, and discovered the evidence in question when

executing that warrant. See United States v. Procopio, 88 F.3d

21 , 27 (1st Cir. 1996) (applying the inevitable discovery doctrine

to admit the illegally uncovered contents of a briefcase where

there was "little reason to doubt that the local police would have

contacted federal agents, even without the information gleaned

during the search," and where it was "even more certain that

- 15 -

federal agents . . . would have then sought a warrant to search

the briefcase"). Thus, because the Task Force members need not

have actually obtained a warrant to rely on the inevitable

discovery exception, any defects in the warrant that they did

obtain the day after their initial warrantless entry of Soto-

Peguero's apartment are not directly relevant to the question of

whether the evidence at issue must be suppressed. See Silvestri,

787 F.2d at 744 (contemplating situations where a warrantless

search is never followed by a warrant and yet the government relies

on the inevitable discovery doctrine).

Moreover, here, the United States has made the required

showing under the inevitable discovery doctrine. In that regard,

Soto-Peguero does not challenge Special Agent Rideout's testimony

that he would have pursued a warrant regardless of what was found

in securing the apartment. He also does not argue that, if the

Task Force members had delayed entry until they obtained a valid

search warrant, they would not have found the evidence in question

upon its execution.

To the extent that we can read Soto-Peguero's claim that

the warrant application would have been insufficient without the

illegally obtained evidence as an argument that the police did not

have probable cause to search his home before they entered it, we

disagree. Soto-Peguero and Cabral lived together at the searched

location; he spoke to Mejia-Ramos on July 6, indicating that he

- 16 -

would deliver heroin that day; he told Mejia-Ramos that Cabral was

on her way around 9:38 p.m., four minutes after she had left their

apartment; and Cabral was then stopped with close to a kilogram of

heroin in her pocketbook. We thus agree with the District Court

that "the officers had sufficient probable cause" to substantiate

a search warrant for Soto-Peguero's apartment before the

protective sweep even began. Soto-Peguero, 252 F. Supp. 3d at 13 .

B.

Soto-Peguero separately argues that the District Court

erred in insulating the evidence at issue from the exclusionary

rule by adverting to our precedent that, in analyzing whether to

admit evidence through the inevitable discovery doctrine, we must

also consider whether doing so would "encourage police misconduct"

and thereby "sully the prophylaxis of the Fourth Amendment."

United States v. Hughes, 640 F.3d 428 , 440-41 (1st Cir. 2011)

(quoting Zapata, 18 F.3d at 978 ). In undertaking that inquiry, we

need to "dwell[] closely on the facts" and look toward whether the

record establishes that law enforcement officers intentionally

violated the Fourth Amendment as well as the incentives, if any,

for them to act unconstitutionally. United States v. Scott, 270

F.3d 30 , 45 (1st Cir. 2001); see also Hughes, 640 F.3d at 441 .

But, rather than develop an argument along those precise lines,

Soto-Peguero instead directs our attention to an out-of-circuit

case, United States v. Madrid, 152 F.3d 1034 (8th Cir. 1998).

- 17 -

There, the Eighth Circuit recognized an exception to the inevitable

discovery doctrine because police behaved egregiously and

"exploited their presence" in the defendant's home. Id. at 1040. Either way, Soto-Peguero's attempt to make the case that the

conduct by law enforcement here precludes us from affirming the

District Court's inevitable discovery ruling fails.

Invoking Madrid, Soto-Peguero cites to a number of

instances of purported misconduct that he argues necessitate

suppression even if the inevitable discovery exception otherwise

would apply. Specifically, he alleges that the Task Force members

"tore the residence apart," "destroy[ed] furniture," "open[ed]

drawers," "open[ed] containers," "pr[ied] the lid off [an] air

conditioning vent," and "used this illegally obtained evidence to

secure the warrant" during their first entry to his apartment. He

also contends that admitting this evidence would "make[] the court

complicit in the officers' false testimony at the suppression

hearing."

Soto-Peguero makes the allegation that Task Force

members "tore the residence apart" and "destroy[ed] furniture" in

support of his Madrid-based argument for the first time on appeal.

Thus, our review of it is at most for plain error. See United

States v. Lara, 970 F.3d 68 , 76 (1st Cir. 2020). We find none, as

the District Court was not asked to make a finding about what, if

any, damage the Task Force members caused in going through the

- 18 -

apartment during their initial entry and the District Court did

not do so on its own. See United States v. Takesian, 945 F.3d

553 , 563 (1st Cir. 2019) (explaining that "if an error pressed by

the appellant turns on 'a factual finding [he] neglected to ask

the district court to make, the error cannot be clear or obvious

unless' he shows that 'the desired factual finding is the only one

rationally supported by the record below'" (quoting United States

v. Olivier-Diaz, 13 F.3d 1 , 5 (1st Cir. 1993))).

We turn, then, to the aspects of Soto-Peguero's Madrid-

based argument that rely on the remaining allegations of

misconduct. In part, Soto-Peguero relies on the assertion that

the record evidence indicates that Task Force members opened the

drawer of the nightstand and looked inside the floor vent when

they went through the apartment without a warrant. But, even

accepting that the evidence supports that understanding of their

conduct, it still "falls short of the blatant search through

personal effects in Madrid," just as we concluded the last time

that a criminal defendant asked us to follow the Eighth Circuit's

lead. United States v. Dent, 867 F.3d 37 , 41 (1st Cir. 2017); see

id. (holding that when an officer exceeded the scope of a

protective sweep by looking under an air mattress, that did not

bring the case within Madrid's purview).

So, that leaves only Soto-Peguero's contentions that the

inclusion of a description of the evidence turned up during the

- 19 -

warrantless entry in the warrant affidavit and "the officers' false

testimony" at the suppression hearing satisfy the Madrid standard,

at least when considered in the context of how the officers

conducted themselves at that time. We assume, for the sake of

argument only, that the Eighth Circuit's holding that the officers

in Madrid "exploited their presence" in the defendant's home

extends to encompass this flavor of alleged misconduct. Even

still, here, too, we are not persuaded.

The affidavit attached to the search warrant application

did describe evidence that Task Force members uncovered pursuant

to what that affidavit characterized as a "security sweep." And,

as Soto-Peguero notes, the District Court later found that some of

that evidence was obtained through methods that exceeded the scope

of such a sweep. But, we do not see how this mismatch suffices to

support Soto-Peguero's Madrid-based suppression argument. The

Task Force members had been shot at as they tried to enter the

residence and would later testify that they found the evidence

while trying to secure the apartment and locate the firearm in

question. In such circumstances, we cannot say that the warrant

application's erroneous description of the means by which that

evidence had been acquired constitutes the kind of egregious

conduct that, per Madrid, could justify suppression. Cf. United

States v. Paradis, 351 F.3d 21 , 29 n.7 (1st Cir. 2003) (describing

scenarios in which a protective sweep might properly authorize an

- 20 -

officer to specifically search for weapons). Consistent with this

conclusion, we note that the District Court made no finding here

that any law enforcement officer involved in the preparation of

the warrant application either knowingly included

unconstitutionally obtained evidence or knowingly misdescribed

that evidence as having been lawfully obtained.

With respect to Soto-Peguero's contention that Madrid

requires suppression here based on his allegation that Task Force

members gave false testimony at the suppression hearing, we are

likewise unpersuaded. The District Court did explain that it was

not fully persuaded by the Task Force members' testimony at the

suppression hearing regarding what happened during the warrantless

entry. But, the District Court also concluded that there was no

basis for finding on this record the kind of egregious or flagrant

official misconduct that would require suppression in order to not

sully the prophylaxis of the Fourth Amendment. Soto-Peguero, 252

F. Supp. 3d at 13 -14. In the face of that ruling and the absence

of any finding by the District Court that the Task Force members

who testified at that hearing did so in bad faith, we see no basis

for requiring suppression even were we to accept Soto-Peguero's

argument that we should adopt the Madrid standard.

Because Soto-Peguero has not succeeded in establishing

that the United States failed to meet the requirements for applying

- 21 -

the inevitable discovery doctrine, we affirm the District Court's

denial of his motion to suppress.

III.

Soto-Peguero also challenges the fact that the Probation

Office applied a two-level role enhancement to increase the

Guidelines range for his drug possession-related crimes from 168-

210 months to 210-262 months.

Under § 3B1.1(c) of the Guidelines, a defendant's

offense level is increased by two levels if "the defendant was an

organizer, leader, manager, or supervisor in any criminal

activity" involving four or fewer participants. For the

enhancement to apply, the government bears the burden of proving,

by a preponderance of the evidence, that "the criminal enterprise

involved at least two complicit participants (of whom the defendant

may be counted as one)" and that "the defendant, in committing the

offense, exercised control over, organized, or was otherwise

responsible for superintending the activities of, at least one of

those other persons." United States v. Cruz, 120 F.3d 1 , 3 (1st

Cir. 1997). "The determination of an individual's role in

committing an offense is necessarily fact-specific. Accordingly,

appellate review must be conducted with considerable deference."

Id. (internal citation omitted). Even a single instance of

managing the actions of others can substantiate the enhancement.

See United States v. Voccola, 99 F.3d 37 , 44 (1st Cir. 1996).

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Soto-Peguero argues that the entirety of the

government's case for the enhancement is that, on two occasions,

he stated that he was "sending" Cabral. He asserts that, beyond

that, there is nothing in the record to support the conclusion

that he and Cabral "were anything other than equal participants in

criminal activity."

The United States points out that Soto-Peguero had

"scores of communications" with Mejia-Ramos, while Cabral only

interacted with him to ask to which house she should go. On one

occasion, Mejia-Ramos contacted Soto-Peguero and told him the

heroin was poor quality. Soto-Peguero replied: "My woman is on

the way." Later, Cabral retrieved what were presumably the

inferior drugs from Mejia-Ramos's cousin. On another occasion,

after Cabral dropped off a package, Mejia-Ramos called Soto-

Peguero to ask what he had sent. Per the government's

characterization, "both Mejia-Ramos and his cousin treated Cabral

as a mere delivery person and engaged only Soto-Peguero in

important business decisions."

At sentencing, the District Court -- after presiding

over a six-day trial and observing both Soto-Peguero and Cabral

-- concluded that "Soto-Peguero was running the show." He "told

[Cabral] to go to Brockton or wherever it was on a number of

occasions." That was where she "ultimately got caught."

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Based on all the evidence cited by the United States,

and accounting for the fact that the District Court had the

opportunity to observe the witnesses and the defendant firsthand,

we cannot conclude that the District Court clearly erred in holding

that the government had shown by a preponderance of the evidence

that Soto-Peguero was managing or supervising Cabral on at least

one occasion. We therefore affirm the District Court's decision.

IV.

As described above, we affirm both Soto-Peguero's

convictions and his sentence.

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