United States v. Sierra-Ayala

39 F.4th 1

• Court: Court of Appeals for the First Circuit
• Decided: July 5, 2022
• Docket: 20-1145P
• Status: Published

Opinion

United States Court of Appeals For the First Circuit

No. 20-1145

UNITED STATES OF AMERICA,

Appellee,

v.

LUIS MIGUEL SIERRA-AYALA,

Defendant, Appellant.

APPEAL FROM THE UNITED STATES DISTRICT COURT FOR THE DISTRICT OF PUERTO RICO

[Hon. Pedro A. Delgado-Hernández, U.S. District Judge]

Before

Barron, Chief Judge, Selya and Lipez, Circuit Judges.

Kevin E. Lerman, with whom Eric Alexander Vos, Federal Public Defender, and Franco L. Pérez-Redondo, Assistant Federal Public Defender, Supervisor, Appeals Division, were on brief, for appellant. Francisco A. Besosa-Martínez, with whom W. Stephen Muldrow, United States Attorney, and Mariana E. Bauzá-Almonte, Assistant United States Attorney, Chief, Appellate Division, were on brief, for appellee.

July 5, 2022 LIPEZ, Circuit Judge. On January 29, 2017, Luis Miguel

Sierra-Ayala was standing near his parents' house in Loíza, Puerto

Rico, holding a black Adidas bag, when officers from the Puerto

Rico Police Department arrived and gave chase to several other

individuals who had been standing nearby. One of the officers

approached Sierra-Ayala and discovered drugs within the bag. After

arresting him, the officer discovered a handgun with an obliterated

serial number on Sierra-Ayala's person. Sierra-Ayala filed a

motion to suppress the evidence recovered during his arrest,

arguing that he was seized in violation of the Fourth Amendment

and that he was coerced into handing over the bag, which he claimed

to be safeguarding for his cousin. After the district court denied

the motion to suppress, Sierra-Ayala was convicted of four offenses

relating to the possession of the weapon and the drugs. Sierra-

Ayala appeals from this conviction, seeking review of the district

court's denial of the motion to suppress and of limitations on

cross-examination imposed during the trial. We affirm.

I.

A. Factual Background

We recite the "facts in the light most favorable to the

district court's ruling" on Sierra-Ayala's motion to suppress,

"noting where relevant [Sierra-Ayala]'s contrary view of the

testimony presented at the suppression hearing." United States v.

Rodríguez-Pacheco, 948 F.3d 1, 3 (1st Cir. 2020) (first quoting

- 2 - United States v. Camacho, 661 F.3d 718, 723 (1st Cir. 2011); and

then quoting United States v. Young, 835 F.3d 13, 15 (1st Cir.

2016)).

1. The January 29, 2017 Operation

On January 29, 2017, officers from the Puerto Rico Police

Department ("PRPD") deployed to a "known drug point" on Melilla

Street in Loíza, Puerto Rico. The operational plan was to conduct

surveillance and to act if the officers observed criminal activity.

Melilla Street is a residential street, with houses on both sides.

The drug point targeted by the PRPD operational plan was in a

wooded area of Melilla Street, near a vacant lot.

At about 8:50 a.m., PRPD officers arrived at the drug

point in six or seven vehicles. Two vehicles were marked with the

PRPD emblem and the rest were unmarked. Sergeant Jesús López-

Maysonet was dressed in plainclothes and traveled with two fellow

officers, Hector Garcia Nieves and Daniel López Garcia, in an

unmarked car. As he arrived at the drug point, the sergeant

observed seven or eight individuals with messenger-style bags. He

testified that, based on his training and experience, this type of

bag is frequently used to carry drugs and weapons. Sergeant López-

Maysonet parked the car he was driving in a yard next to a house.

The three officers then exited the vehicle and identified

themselves as police officers by shouting "police." All but one

of the individuals fled into the adjacent wooded area. As Officers

- 3 - Garcia Nieves and López Garcia chased the fleeing individuals,

other officers were arriving at the site.

Sierra-Ayala was the man who did not flee; he remained

sitting in a plastic chair as Sergeant López-Maysonet approached.

The sergeant testified that Sierra-Ayala was wearing a black

messenger-style bag across his chest. At the initial suppression

hearing before the magistrate judge, López-Maysonet testified that

after he identified himself to Sierra-Ayala as a police officer,

Sierra-Ayala stood up, turned to the right, and showed him the

contents of the bag. Sierra-Ayala testified differently. He

claimed that he was concerned for his safety when Sergeant López-

Maysonet approached him, and that the sergeant directed him to

turn over the bag, which he had been holding in his hands. Sierra-

Ayala testified that he complied with Sergeant López-Maysonet's

request because he did not feel free to disobey the officer's

direction. Ultimately, the magistrate judge credited Sergeant

López-Maysonet's version of the interaction.

When the sergeant looked inside the bag, he saw "a

transparent plastic bag" containing "purple packages that are used

to pack heroin." Upon seeing the packaging, he informed Sierra-

Ayala that he was under arrest, directed him to stand up, and read

him his Miranda rights. Because Sergeant López-Maysonet did not

have handcuffs on his person, he radioed for backup. After Sierra-

Ayala was handcuffed, he patted him down and identified a gun in

- 4 - a holster on the left side of Sierra-Ayala's belt. López-Maysonet

also testified that he retrieved $94 in cash from Sierra-Ayala's

pockets. Sierra-Ayala testified that only $10 belonged to him and

that the remainder of the cash was recovered from the bag belonging

to his cousin.

2. Sierra-Ayala's Involvement

Sierra-Ayala testified at the two suppression hearings

about how he came to be at the drug point on Melilla Street on

January 29, 2017. Because this testimony is relevant to Sierra-

Ayala's motion to suppress, we summarize it here.

Sierra-Ayala grew up in a house on Melilla Street about

five or six houses away from the site of his arrest. Although he

now lives with his wife and two children in a different area of

Loíza, Sierra-Ayala returned to his parents' house on Melilla

Street between 6:00 and 7:00 a.m. on January 29, 2017 to work on

a Nissan Pathfinder that he was keeping and repairing there. On

the morning of his arrest, Sierra-Ayala was waiting for his friend

Jose Carlos, who was going to help him remove the radiator from

the Pathfinder and take him to purchase a replacement.

At about 8:30 a.m., Sierra-Ayala stopped working on his

car and went to buy a soda and cigarettes from his cousin, who

sells refreshments from his grandmother's house. This house is

across the street from Sierra-Ayala's parents' house. Because the

items Sierra-Ayala wished to purchase cost around $3 and his cousin

- 5 - did not have change for Sierra-Ayala's $10 bill, Sierra-Ayala went

off in search of change. He walked toward a group of individuals

further down Melilla Street -- which included another one of

Sierra-Ayala's cousins, Jean Carlos Sirino -- and attempted to get

change from Jean Carlos. While Jean Carlos searched for change,

he passed the bag he was holding to Sierra-Ayala. Sierra-Ayala

testified that the zipper of the bag was closed, and that he had

been holding the bag for "[a]round five seconds" when the PRPD

officers arrived. As discussed above, Sierra-Ayala testified that

the officers' arrival and Sergeant López-Maysonet's approach and

alleged order made him feel that he had no choice but to hand over

the bag.

B. Procedural History

Sierra-Ayala pled not guilty to four charged offenses.

He filed a motion to suppress the gun and drugs discovered by

Sergeant López-Maysonet, arguing that the sergeant lacked

reasonable suspicion to support the initial seizure and that the

discovery of contraband in the bag was coerced.1 Sierra-Ayala

argued that his presence on Melilla Street was not unusual and

that he was not engaged in any suspicious activity when the

officers arrived in their vehicles. In response, the government

1 Sierra-Ayala also sought to suppress his post-arrest statements, on the basis that they were the fruit of an illegal arrest.

- 6 - argued that Sierra-Ayala was not seized at the time Sergeant López-

Maysonet approached him, and that López-Maysonet acquired probable

cause to arrest Sierra-Ayala after Sierra-Ayala voluntarily

displayed the contents of his bag.

1. Initial Suppression Hearing Before the Magistrate Judge

The magistrate judge held a hearing on Sierra-Ayala's

motion to suppress. Sergeant López-Maysonet and Sierra-Ayala were

the only witnesses, and they testified to the facts as outlined

above. During cross-examination, the sergeant testified that he

had forgotten to identify the holster seized from Sierra-Ayala in

two separate reports filed after the arrest.

Prior to defense counsel's cross-examination of Sergeant

López-Maysonet, the government provided the court with information

on four administrative complaints that had been filed against the

sergeant. The magistrate judge determined that only one incident

had the potential to be Giglio material,2 and permitted defense

counsel to cross-examine López-Maysonet about the incident. The

following exchange occurred:

[Defense Counsel]: Sergeant [López-]Maysonet, there was an administrative complaint against you as a result of a theft or loss of monies during a warrant –- execution of a warrant. Is that correct?

2 See Giglio v. United States, 405 U.S. 150, 154-55 (1972) (holding that evidence relevant to the credibility of a government witness must be disclosed); Roe v. Lynch, 997 F.3d 80, 82 (1st Cir. 2021) (reciting the holding of Giglio).

- 7 - [López-Maysonet]: That’s not right.

After Sergeant López-Maysonet reviewed the administrative

complaint, he explained:

[López-Maysonet]: Like I was telling you, I was the supervisor and I did the writ for the Lieutenant [Daniel López García].

[Defense]: Is that administrative complaint as against you or is it as against someone else, the [complaint] in front of you?

[López-Maysonet]: It's against Officer Daniel Lopez [García].

[Defense]: It's not against you?

[López-Maysonet]: No.

[Defense]: Does your name appear in that document?

[López-Maysonet]: It only shows my last name, Lopez Maysonet.

. . .

[Defense]: What is the nature of the allegation?

[López-Maysonet]: The nature of the allegation was that when I was supervising a search and arrest, the person that was subject of the warrant, Mr. Abner Arroyo, . . . gave me some money, I counted the money and then an amount of money went missing. We went to the video, we saw the video again and then there was some money missing when I was counting it and then Officer Lopez Garcia said that he had taken it as a joke in order for us to see what happens when someone else from outside gets involved.

Officer López García was involved in the operation that led to

Sierra-Ayala's arrest. According to Sergeant López-Maysonet,

- 8 - Officer López García "was in the vehicle but was not present at

the arrest. He was in the wooded area while [Sergeant López-

Maysonet] was arresting" Sierra-Ayala.

At the end of the hearing, the magistrate judge directed

the parties to file simultaneous supplemental briefs addressing

whether Sierra-Ayala had a reasonable expectation of privacy in

the contents of the bag.

2. The Magistrate Judge's Report and Recommendation

In its supplemental brief, the government argued that

Sierra-Ayala lacked standing to challenge a Fourth Amendment

violation because he had no privacy interest in the bag.3 The

government noted that Sierra-Ayala testified that his cousin had

passed him the bag and that he had held it for only five to thirty

seconds before the officers arrived. The government also argued

that the court should credit Sergeant López-Maysonet's hearing

testimony rather than Sierra-Ayala's because Sierra-Ayala's

narrative contained several implausibilities.

Sierra-Ayala's supplemental brief argued for the

opposite conclusion. In particular, Sierra-Ayala argued that he

had a possessory interest in the bag in the form of a bailment,

giving rise to a reasonable expectation of privacy, and that

3 As the magistrate judge noted, "standing" for Fourth Amendment purposes is distinct from Article III standing. Byrd v. United States, 138 S. Ct. 1518, 1530 (2018); see also infra Section II.C.

- 9 - Sergeant López-Maysonet's testimony was incredible and

embellished. Sierra-Ayala also reiterated his argument that the

encounter with Sergeant López-Maysonet was a seizure rather than

a consensual encounter, and that López-Maysonet lacked reasonable

suspicion for the stop.

In a Report and Recommendation, the magistrate judge

credited Sergeant López-Maysonet's testimony about how the

incident on January 29 unfolded. The magistrate judge described

López-Maysonet's demeanor and tone as convincing, and his version

of the events as plausible and logical. The judge found Sierra-

Ayala's testimony facially less plausible for several reasons.

First, the magistrate judge expressed skepticism about the

reported price of Sierra-Ayala's intended purchases and the lack

of change for a relatively small bill in a home business selling

inexpensive items. The judge also found the suggestion that

Sierra-Ayala had only been holding the bag for five seconds before

the PRPD officers arrived not credible. The magistrate judge

credited López-Maysonet's testimony that "he said nothing other

than that he was a police officer. Sierra-Ayala then stood up and

showed Lopez the contents of the shoulder bag without any other

prompting."

Finding that Sierra-Ayala voluntarily displayed the

contents of the bag to López-Maysonet, and that the officers' show

of force upon arriving to Melilla Street would not have caused a

- 10 - reasonable person to believe he was not free to leave, the

magistrate judge recommended that the district court find that

Sierra-Ayala was not seized. The Report and Recommendation also

concluded that Sierra-Ayala lacked standing to challenge the

search and seizure of the bag because he lacked a reasonable

expectation of privacy in the bag. The magistrate judge

recommended that the court deny Sierra-Ayala's motion to suppress

for both of these reasons.

Sierra-Ayala objected to the Report and Recommendation

and requested a de novo hearing before the district court.4

Specifically, Sierra-Ayala objected to the magistrate judge's

favorable assessment of Sergeant López-Maysonet's credibility and

to the magistrate judge's conclusions that no Fourth Amendment

seizure occurred and that Sierra-Ayala lacked standing to

challenge the search of the bag.

3. De Novo Hearing Before the District Court

The district court scheduled a de novo hearing in

response to Sierra-Ayala's objection to the Report and

Recommendation. The government subsequently filed a motion to

vacate the de novo hearing, which the district court denied. The

4Under 28 U.S.C. § 636(b)(1), the district court "shall make a de novo determination of those portions of the [Report and Recommendation] to which objection is made." In doing so, the court "may . . . receive further evidence" on the matter, id., including via an evidentiary hearing, see United States v. Lawlor, 406 F.3d 37, 40 (1st Cir. 2005).

- 11 - government then filed a motion to limit the scope of the de novo

hearing to the question of standing, arguing that it presented a

threshold issue because "the legality of the seizure is not

properly before the Court" until Sierra-Ayala establishes

standing. The district court granted that motion two days later,

without waiting for a response from Sierra-Ayala.

At the de novo hearing, Sierra-Ayala and Sergeant López-

Maysonet reiterated much of their testimony from the initial

suppression hearing before the magistrate judge. Sierra-Ayala

testified that when his cousin handed him the bag, it was his

understanding that he "w[as] to hold th[e] bag until [Jean Carlos]

got change for [Sierra-Ayala]," he was "responsible for th[e] bag,"

and it was his understanding that he "could not give it to anyone

else." Sierra-Ayala explained that he "turned [the bag] over to

the police[] because [Sergeant López-Maysonet] told [him] to turn

it over." Sierra-Ayala also testified that he was at the site for

only about five seconds before police arrived, and that his cousin

had never asked him to watch anything in the past. He explained

that the site of his arrest was "[f]our or five houses" away from

his mother's house. Sergeant López-Maysonet reiterated his prior

testimony that Sierra-Ayala had displayed the contents of the bag

to him voluntarily.

After the de novo hearing, the district court

subsequently issued an opinion and order "adopt[ing] the R&R's

- 12 - recommendation as it relates to the issue of standing, and

den[ying] Sierra-Ayala's motion on such basis." The court assumed,

"[f]or purposes of this Opinion and Order, . . . that the

interaction between Sierra-Ayala and Sergeant López[-Maysonet]

occurred the way Sierra-Ayala described it." In other words, the

court assumed that Sergeant López-Maysonet ordered Sierra-Ayala to

display the contents of the bag to him, but nevertheless concluded

that Sierra-Ayala lacked standing to challenge the search.5

In finding that Sierra-Ayala lacked standing, the

district court concluded that Sierra-Ayala was authorized to

possess the bag but that the evidence was insufficient to support

a depositor-depository relationship between Sierra-Ayala and his

cousin.6 Moreover, even if such a relationship existed, the court

concluded that a bailment was not necessarily sufficient to

establish a reasonable expectation of privacy. Instead, the court

found that Sierra-Ayala "undertook no affirmative precautions to

maintain privacy" even though the court assumed, for purposes of

5 As discussed infra, the district court subsequently abandoned this assumption and expressly found that Sierra-Ayala voluntarily displayed the contents of the bag to Sergeant López- Maysonet. 6 "The depositum contract is a civil law concept, existing in Louisiana as well as Puerto Rico, that has some relationship with the common law concept of bailment." Jewelers Mut. Ins. Co. v. N. Barquet, Inc., 410 F.3d 2, 12 (1st Cir. 2005). A depository assumes a duty of care to the depositor to safeguard the object. Id. at 14.

- 13 - the order, that Sierra-Ayala's version of the events was accurate.7

The court observed that "[t]he record is silent on whether [Sierra-

Ayala] had a subjective expectation that the bag was to remain

free from governmental intrusion." Because the court found that

Sierra-Ayala lacked standing to challenge the discovery of the

drugs, it did not make a credibility determination beyond its

assumption, for purposes of resolving the question of standing,

that Sierra-Ayala's testimony accurately described the situation.

4. The District Court's Supplemental Order

After the district court issued its order adopting the

Report and Recommendation with respect to Sierra-Ayala's standing

to challenge the search of the bag, defense counsel sought a

supplemental order on Sierra-Ayala's standing to suppress the gun,

which Sergeant López-Maysonet testified to finding on Sierra-

Ayala's person. The court allowed the parties to address the issue

at a pre-trial status conference. At the conference, defense

counsel argued that Sierra-Ayala's lack of standing to suppress

the contents of the bag was irrelevant to whether he had standing

to challenge the discovery of the gun on his person. Defense

counsel also argued that, even if the court credited Sergeant

López-Maysonet's version of the events, Sierra-Ayala's display of

the bag could not be voluntary under the fruit-of-the-poisonous-

7 Again, according to Sierra-Ayala, he only turned the bag over to Sergeant López-Maysonet after being ordered to do so.

- 14 - tree doctrine because Sierra-Ayala was illegally seized when

Sergeant López-Maysonet approached.

During the status conference, the district court

indicated on multiple occasions that it was crediting Sergeant

López-Maysonet's testimony, rather than Sierra-Ayala's, about how

the encounter unfolded.8 After the status conference, the district

court issued a supplemental order, which summarized the factual

findings the district court had adopted at the status conference:

[T]he defendant was with a group of individuals who ran away when police officers arrived in the area. The defendant, however, stayed in place. One of the officers (Sergeant López[-Maysonet]) approached the defendant, identifying himself as a police officer. The defendant held open and showed the contents of the bag to the officer, who saw a clear plastic bag that had purple packages in it, which the officer knew was the type of packaging used for heroin. The officer placed the defendant under arrest and frisked him, finding the gun.9

The court rejected Sierra-Ayala's argument that he was seized at

the time Sergeant López-Maysonet approached, and concluded that,

because Sierra-Ayala voluntarily displayed the contents of the

bag, the sergeant had probable cause to arrest him. The court

concluded that the discovery of the gun on Sierra-Ayala's person

Defense counsel objected to the court's finding 8 that Sergeant López-Maysonet's approach to Sierra-Ayala was constitutional. In the same order, the district court also indicated that 9

it "[wa]s in agreement with the Magistrate Judge's factual analysis."

- 15 - was therefore a permissible consequence of a constitutional search

incident to arrest.

5. Trial

At the start of the trial, the government sought to

preclude the defense from questioning Sergeant López-Maysonet

about the 2015 incident in which he failed to file a timely report

about the misconduct of his supervisee, Officer Daniel López

García. The government argued that the incident was not relevant

under Giglio. Defense counsel countered that the incident was

relevant to Sergeant López-Maysonet's truthfulness under Federal

Rule of Evidence 608 and his potential bias. Defense counsel also

sought to introduce the sergeant's statements from the suppression

hearing as a prior inconsistent statement.

The district court ruled that defense counsel could not

cross-examine Sergeant López-Maysonet about the incident, noting

that "[López-Maysonet] submitted the report. He did it late.

That's not . . . [Rule] 608 material." The court also precluded

defense counsel from introducing Sergeant López-Maysonet's

testimony at the initial suppression hearing as a prior

inconsistent statement. The court explained that whether López-

Maysonet was "under investigation at the time of the arrest of Mr.

Sierra-Ayala" was "not what was asked of [López-Maysonet] . . . .

Defense counsel was very specific, and they were referring to a

- 16 - complaint as a result of a theft or loss of monies during [the]

execution of a warrant."

The trial commenced after the resolution of these

threshold issues. Sergeant López-Maysonet reiterated his prior

testimony that Sierra-Ayala voluntarily displayed the contents of

the bag to him. Sergeant López-Maysonet also testified to

recovering the holster from Sierra-Ayala's person but acknowledged

that he failed to document it in the investigatory report filed

after the incident. The jury convicted Sierra-Ayala of the four

charged offenses.10 He was sentenced to a term of seventy-two

months of imprisonment. This appeal followed.

C. Claims on Appeal

Appellant seeks review of the district court's denial of

his motion to suppress the drugs and firearm. He argues that the

fruit-of-the-poisonous-tree doctrine applies to the evidence

seized during his encounter with Sergeant López-Maysonet because

the encounter was an unconstitutional seizure. The government

responds that Sierra-Ayala was not seized when Sergeant López-

Maysonet approached and that he voluntarily displayed the contents

of the bag to the sergeant. Alternatively, the government suggests

10The offenses of conviction were: possession of a firearm in furtherance of a drug trafficking crime; possession with intent to distribute a controlled substance (heroin); possession with intent to distribute a controlled substance (crack cocaine); and possession of a firearm with an obliterated serial number.

- 17 - that the interactions between Sierra-Ayala and Sergeant López-

Maysonset constitute a constitutionally permissible investigatory

stop under Terry v. Ohio, 392 U.S. 1 (1968). Moreover, even if

the initial stop of Sierra-Ayala was unconstitutional, the

government contends that the fruit-of-the-poisonous-tree doctrine

does not apply to the items seized because their discovery

comported with Fourth Amendment principles.

Appellant also appeals the district court's decision,

during his trial, to preclude cross-examination of Sergeant López-

Maysonet on certain issues relating to the administrative

complaint in which Sergeant López-Maysonet was named. Appellant

suggests that cross-examination on this issue is relevant to

truthfulness -- i.e., Sergeant López-Maysonet's "dishonest[]"

conduct in belatedly filing a report about the incident -- and

bias -- i.e., that Sergeant López-Maysonet had an incentive to

testify favorably for the government because he was under

investigation. Appellant contends that the district court abused

its discretion in denying cross-examination and that his inability

to adequately impeach Sergeant López-Maysonet's bias and

truthfulness caused his trial to be fundamentally unfair.

- 18 - II.

We address appellant's suppression arguments first.

A. Standard of Review

We review the district court's factual findings at the

suppression hearing for clear error and its legal conclusions de

novo. Rodríguez-Pacheco, 948 F.3d at 6. We are "especially

deferential" to the district court's evaluation of witnesses'

credibility, which we will overturn "only if, after reviewing all

of the evidence, we have a 'definite and firm conviction that a

mistake has been committed.'" United States v. Jones, 187 F.3d

210, 214 (1st Cir. 1999) (quoting United States v. Rostoff, 164

F.3d 63, 71 (1st Cir. 1999)). "Indeed, absent objective evidence

that contradicts a witness's story or a situation where the story

itself is so internally inconsistent or implausible that no

reasonable factfinder would credit it, 'the ball game is virtually

over' once a district court determines that a key witness is

credible." United States v. Guzmán-Batista, 783 F.3d 930, 937

(1st Cir. 2015) (citation omitted) (quoting Rivera-Gómez v. de

Castro, 900 F.2d 1, 4 (1st Cir. 1990)).

B. The Seizure

The Fourth Amendment prohibits "unreasonable searches

and seizures." U.S. Const. amend. IV. Evidence acquired in

violation of the Fourth Amendment is subject to the exclusionary

rule. Camacho, 661 F.3d at 724. But "[n]ot every interaction

- 19 - between a police officer and a citizen constitutes a seizure

triggering Fourth Amendment protections." United States v. Ford,

548 F.3d 1, 4 (1st Cir. 2008); see also Florida v. Royer, 460 U.S.

491, 497-98 (1983) (plurality opinion). Instead, a seizure occurs

where the "totality of the circumstances" shows that officers have

"'restrained the liberty of a citizen' through 'physical force or

[a] show of authority.'" Camacho, 661 F.3d at 725 (quoting Terry,

392 U.S. at 19 n.16). Courts evaluate the "'coercive effect of

[an] encounter' by asking whether 'a reasonable person would feel

free to decline the officers' requests or otherwise terminate the

encounter.'" Id. (quoting Brendlin v. California, 551 U.S. 249,

255 (2007)).

Here, appellant was clearly seized when Sergeant López-

Maysonet approached him at the site on Melilla Street. Immediately

preceding Sergeant López-Maysonet's approach, an unmarked vehicle

had pulled up in a yard beside a house. Three officers exited the

vehicle, yelling "police." The officers chased after six or seven

fleeing individuals -- individuals who had not been observed

engaging in criminal activity prior to the officers' pursuit.

Additional police officers and vehicles arrived at the site as the

two pursuing officers ran into the woods. A reasonable person,

observing this show of police authority, would not feel free to

leave. The heavy police presence and rapidity with which officers

pursued the fleeing individuals "objectively communicate[d] that

- 20 - [law enforcement] [wa]s exercising [its] official authority to

restrain the individual[s'] liberty of movement." United States

v. Fields, 823 F.3d 20, 25 (1st Cir. 2016) (second and fourth

alterations in original) (emphasis omitted) (quoting United States

v. Cardoza, 129 F.3d 6, 16 (1st Cir. 1997)).

Even where an encounter with law enforcement rises to

the level of a seizure, however, the Supreme Court has recognized

certain exceptions to the protections of the Fourth Amendment.

The government argues that even if Sierra-Ayala was seized when

Sergeant López-Maysonet approached him, the Terry exception

applies. See 392 U.S. at 30-31. Under Terry, "a police officer

may briefly detain an individual for questioning if the officer

'reasonably suspects that the person apprehended is committing or

has committed a crime.'" Camacho, 661 F.3d at 726 (quoting Arizona

v. Johnson, 555 U.S. 323, 326 (2009)). The reasonable suspicion

standard requires "a 'particularized and objective basis' for

suspecting the person stopped of criminal activity," id. (quoting

Ornelas v. United States, 517 U.S. 690, 696 (1996)), that is "both

objectively reasonable and 'grounded in specific and articulable

facts,'" id. (quoting United States v. Hensley, 469 U.S. 221, 229

(1985)). Critically, "the individual facts, taken in the

aggregate," must be "sufficient to trigger a reasonable suspicion

that some criminal activity was afoot -- and that the defendant

- 21 - was involved." United States v. Ruidíaz, 529 F.3d 25, 30 (1st

Cir. 2008) (emphasis added).

In arguing that Sergeant López-Maysonet possessed

reasonable suspicion to justify a Terry stop of Sierra-Ayala, the

government points to three facts: (1) the location of the stop,

which Sergeant López-Maysonet described as a "known drug point"

based on his training and experience; (2) the fact that several

individuals were carrying messenger-style bags, which Sergeant

López-Maysonet testified were "used to carry controlled substances

and weapons"; and (3) the flight of several individuals upon the

arrival of police.

The location of a stop in a "high crime area" may be one

factor relevant to the Terry analysis. Illinois v. Wardlow,

528 U.S. 119, 124 (2000); United States v. Wright, 485 F.3d 45, 54

(1st Cir. 2007). But the Supreme Court has made clear that "[a]n

individual's presence in an area of expected criminal activity,

standing alone, is not enough to support a reasonable,

particularized suspicion that the person is committing a crime."

Wardlow, 528 U.S. at 124 (emphasis added). Although "unprovoked

flight" or "nervous, evasive behavior" may provide reasonable

suspicion justifying an investigatory stop, id. at 124; see also

United States v. Aitoro, 446 F.3d 246, 252 (1st Cir. 2006), Sierra-

Ayala -- unlike the other individuals present -- neither fled nor

acted evasively as Sergeant López-Maysonet approached, see

- 22 - Camacho, 661 F.3d at 726. Nor is Sierra-Ayala's possession of a

black messenger-style bag enough to tip the scale toward reasonable

suspicion. Even if messenger-style bags are commonly used in drug

transactions, as Sergeant López-Maysonet testified, they are also

useful for any number of legitimate purposes. Sergeant López-

Maysonet did not observe individuals using the bags in a way that

a "reasonably prudent and experienced police officer would have

recognized . . . as consistent with the consummation of a drug

deal." United States v. Rabbia, 699 F.3d 85, 90 (1st Cir. 2012).

The totality of the circumstances here does not provide

an "objectively reasonable, particularized basis for suspecting

[Sierra-Ayala] of criminal activity." Camacho, 661 F.3d at 726

(emphasis added); see also United States v. Wright, 582 F.3d 199,

220 (1st Cir. 2009) (Lipez, J., dissenting) ("[T]he reasonable

suspicion justifying a Terry stop must be more than an 'inchoate

and unparticularized suspicion or "hunch,"' and it must be

specifically focused on the individual under scrutiny." (citation

omitted) (quoting Terry, 392 U.S. at 27)). The most that can be

said is that Sierra-Ayala was standing near a known drug point --

close to his parents' home -- while holding a bag that can be used

to transport drugs, weapons, gym clothes, or any number of other

objects. See Camacho, 661 F.3d at 726 ("'The men were walking

normally on a residential sidewalk and displayed no apprehension

or nervousness when the officers approached,' and Camacho's

- 23 - responses to [the officer]'s questions 'were direct and non-

evasive.'" (quoting the district court)). He did nothing

reasonably suggestive of criminal activity.

C. The Search and Arrest

Our conclusion that Sergeant López-Maysonet lacked

reasonable suspicion to justify the initial seizure of Sierra-

Ayala does not end the inquiry. The government argues that an

intervening voluntary act -- Sierra-Ayala's display of the

contents of the bag to Sergeant López-Maysonet -- provided

independent probable cause to arrest Sierra-Ayala, rendering any

lack of reasonable suspicion prior to the voluntary act irrelevant

to suppression.11

Appellant offers two arguments in response. First,

appellant contends that the district court clearly erred in

concluding that he spontaneously and voluntarily displayed the

contents of the bag to Sergeant López-Maysonet, thereby obviating

11The government also argues that we need not reach the merits of Sierra-Ayala's suppression arguments because Sierra-Ayala lacks standing to challenge the search of the bag. We do not address the standing issue. Unlike Article III standing, Fourth Amendment "standing" is not jurisdictional, and courts may address whether a seizure or search was adequately supported -- by reasonable suspicion or probable cause and exigent circumstances -- before resolving whether a defendant has standing to challenge the search or seizure. Byrd, 138 S. Ct. at 1530-31. The district court's written order concluded that Sierra-Ayala lacked standing to challenge the discovery of the drugs, and denied the motion to suppress on that basis. Subsequently, the district court also made the factual finding that Sierra-Ayala acted voluntarily in displaying the contents of the bag to Sergeant López-Maysonet.

- 24 - the need for probable cause for a search. Second, appellant argues

that even if the district court properly concluded that he acted

"voluntarily," suppression of the drugs and the firearm is

nevertheless appropriate under the fruit-of-the-poisonous-tree

doctrine. We consider these arguments in turn.

1. A Voluntary Act

At the suppression hearings, the parties presented

opposing testimony on the issue of voluntariness. Sierra-Ayala

testified that Sergeant López-Maysonet observed the contents of

the bag only because he ordered Sierra-Ayala to turn the bag over.

Sierra-Ayala argued then, and argues again on appeal, that Sergeant

López-Maysonet's coercive inspection of the bag was a search within

the meaning of the Fourth Amendment, to which Sierra-Ayala did not

consent. See Royer, 460 U.S. at 497 ("[W]ithout a warrant to

search Royer's luggage and in the absence of probable cause and

exigent circumstances, the validity of the search depended on

Royer's purported consent."). The government, on the other hand,

argues that Sierra-Ayala voluntarily showed Sergeant López-

Maysonet the contents of the bag, such that López-Maysonet's

observation of the bag's contents was not an illegal search under

the Fourth Amendment.

Where the government defends the validity of a search

based on an individual's consent, the government "has the burden

of proving that the necessary consent was obtained and that it was

- 25 - freely and voluntarily given, a burden that is not satisfied by

showing a mere submission to a claim of lawful authority." Royer,

460 U.S. at 497. Sergeant López-Maysonet testified that Sierra-

Ayala "freely and voluntarily" showed him the bag, without any

prompting. After hearing Sierra-Ayala's competing testimony, the

magistrate judge made the factual finding that Sierra-Ayala

voluntarily displayed the bag's contents to Sergeant López-

Maysonet. The Report and Recommendation identified several

factors supporting the magistrate judge's determination that

López-Maysonet's testimony on this point was credible.12 The

district court adopted this factual finding in a written order,

after a de novo suppression hearing and subsequent status

conference that addressed the voluntariness issue.

Although appellant offers several arguments for why the

lower court's credibility assessment of the competing testimony on

voluntariness was wrong,13 he does not identify "objective evidence

12 These factors include López-Maysonet's tone and demeanor and the logic and plausibility of his version of the events, as compared to the inconsistencies and implausibilities of Sierra- Ayala's version of events. The magistrate judge specifically found implausible Sierra-Ayala's testimony regarding the prices of the goods he sought to purchase and the "story . . . that he was literally caught holding the bag." 13Specifically, Sierra-Ayala argues that the district court overlooked the generally implausible nature of Sergeant López- Maysonet's testimony, the nonsensical logic of Sierra-Ayala's supposedly voluntary action, Sergeant López-Maysonet's evasiveness during testimony, and Sergeant López-Maysonet's disciplinary history.

- 26 - that contradicts [Sergeant López-Maysonet's] story." Guzmán-

Batista, 783 F.3d at 937. Nor was Sergeant López-Maysonet's

testimony "so internally inconsistent or implausible that no

reasonable factfinder would credit it." Id. Because appellant's

evidentiary arguments do not leave us with a "definite and firm

conviction" that the district court erred in crediting Sergeant

López-Maysonet's testimony, Jones, 187 F.3d at 214 (quoting

Rostoff, 164 F.3d at 71), the district court did not clearly err

in concluding that Sierra-Ayala displayed the drugs to Sergeant

López-Maysonet without prompting from the sergeant. See United

States v. Casellas-Toro, 807 F.3d 380, 390 (1st Cir. 2015) (noting

that the voluntariness of a consent search is a factual

determination for the district court); accord United States v.

Coraine, 198 F.3d 306, 308 (1st. Cir. 1999). Upon observing the

drugs in the bag due to this voluntary act, Sergeant López-Maysonet

acquired probable cause to arrest Sierra-Ayala and to conduct a

search of him incident to arrest.

Ordinarily, this conclusion would end our inquiry and

warrant affirmance of the district court's order denying Sierra-

Ayala's motion to suppress. But because appellant also argues

that his "voluntary" act is inextricably linked to the initial

unconstitutional seizure that precipitated his display of the bag,

we next address whether suppression is warranted under the fruit-

of-the-poisonous-tree doctrine.

- 27 - 2. Fruit of the Poisonous Tree

The fruit-of-the-poisonous-tree doctrine is an extension

of the Fourth Amendment exclusionary rule that requires "indirect

fruits" recovered after an initial Fourth Amendment violation to

be suppressed if they "bear a sufficiently close relationship to

the underlying illegality." Camacho, 661 F.3d at 729 (quoting New

York v. Harris, 495 U.S. 14, 19 (1990)). Because the exclusionary

rule "is a 'prudential' doctrine" whose "sole purpose . . . is to

deter future Fourth Amendment violations," Davis v. United States,

564 U.S. 229, 236-37 (2011) (quoting Pa. Bd. of Prob. & Parole v.

Scott, 524 U.S. 357, 363 (1998)),14 suppression as fruit of the

poisonous tree is not appropriate where "the connection between

the illegal police conduct and the discovery and seizure of the

evidence is 'so attenuated as to dissipate the taint,'" Camacho,

661 F.3d at 729 (quoting Segura v. United States, 468 U.S. 796,

805 (1984)). "The notion of the 'dissipation of the taint'

attempts to mark the point at which the detrimental consequences

of illegal police action become so attenuated that the deterrent

effect of the exclusionary rule no longer justifies its cost."

United States v. Cordero-Rosario, 786 F.3d 64, 75 (1st Cir. 2015)

14As the Court emphasized in Davis, "[e]xclusion is 'not a personal constitutional right,' nor is it designed to 'redress the injury' occasioned by an unconstitutional search." 564 U.S. at 236 (quoting Stone v. Powell, 428 U.S. 465, 486 (1976)).

- 28 - (quoting Brown v. Illinois, 422 U.S. 590, 609 (1975) (Powell, J.,

concurring)).

In the context of a "voluntary" confession after an

illegal arrest, to which appellant analogizes his situation,

courts examine "[t]he temporal proximity of the arrest and the

confession, the presence of intervening circumstances, and,

particularly, the purpose and flagrancy of the official

misconduct" to determine whether suppression of the statements is

warranted under the fruit-of-the-poisonous tree doctrine. Brown,

422 U.S. at 603-04 (citations and footnote omitted). And, of

closer relevance to the situation here, we have held that the

fruit-of-the-poisonous-tree doctrine may be implicated where an

individual's "voluntary" consent to a search of his belongings

followed an initial Fourth Amendment violation that "significantly

influenced his decision to consent." United States v. Navedo-

Colón, 996 F.2d 1337, 1339 (1st Cir. 1993).15 The "key inquiry"

is "whether, granting establishment of the primary illegality, the

evidence to which instant objection is made has been come at by

exploitation of that illegality or instead by means sufficiently

distinguishable to be purged of the primary taint." Cordero-

15Whether the initial illegality "play[ed] a significant role in obtaining appellant's consent" is a factual question for the district court. Navedo-Colón, 996 F.2d at 1339; see also Cordero- Rosario, 786 F.3d at 73, 78 (remanding for the district court to make the factual finding after reversing the holding "that the searches . . . did not violate the Fourth Amendment").

- 29 - Rosario, 786 F.3d at 75-76 (emphasis added) (quoting Wong Sun v.

United States, 371 U.S. 471, 488 (1963)); accord United States v.

Delgado-Pérez, 867 F.3d 244, 257-58 (1st Cir. 2017).16

Applying these principles, we conclude that the

circumstances of this case do not warrant suppression of the

evidence recovered from Sierra-Ayala as fruits of the poisonous

tree. To start, we recognize that this case differs from the

consented-to search at issue in Navedo-Colón, where the district

court assumed without deciding that the initial alleged illegality

(an illegal x-ray) was unlawful. 996 F.2d at 1338. Here, in

contrast, the district court concluded that Sierra-Ayala was not

seized, and thus it did not consider the fruit-of-the-poisonous-

tree issue. Nevertheless, the district court made factual findings

that give us sufficient information to determine whether Sierra-

Ayala's display of the bag was "obtained by exploitation of the

underlying illegality." See Cordero-Rosario, 786 F.3d at 78

(remanding where "we lack[ed] sufficient information to determine

whether [the] consent was obtained by exploitation of the

underlying illegality"); Navedo-Colón, 996 F.2d at 1338-39

16 Although "[h]ow appellant's mind worked at the time -- whether or not the [initial illegality] significantly influenced" his action -- is a factual determination for the district court that we review for clear error, Navedo-Colón, 996 F.2d at 1339, "[i]n determining the outcome under the attenuation doctrine, the court of appeals does not defer to the district court." United States v. Paradis, 351 F.3d 21, 32 (1st Cir. 2003). In other words, our review is de novo.

- 30 - (holding that although the district court did not "explicitly deny

a causal connection between the x-ray and appellant's consent," a

"[f]air[] read[ing]" of its opinion "indicates that the court

asked, and answered, the correct causal question in deciding

whether to suppress evidence of consent").

Even assuming a causal connection between the voluntary

display of the bag and the initial illegal seizure effected by the

arriving officers' show of authority due to their temporal

proximity, the facts found by the district court do not support

the conclusion that "the causal link . . . is so tight that the

evidence acquired pursuant to that [voluntary act] must be

suppressed." Delgado-Pérez, 867 F.3d at 257 (quoting Cordero-

Rosario, 786 F.3d at 76); see also United States v. Serrano-

Acevedo, 892 F.3d 454, 460 (1st Cir. 2018) (indicating that

suppression is not warranted where the causal link between an

initial illegality and subsequent consent is "sufficiently

attenuated"). Nothing about the behavior of the officers at the

scene generally, or Sergeant López-Maysonet's particular actions

towards Sierra-Ayala, can be read as "exploit[ing]" the primary

illegality, Cordero-Rosario, 786 F.3d at 78, to induce Sierra-

Ayala to display the contents of the bag. See United States v.

Smith, 919 F.3d 1, 12 (1st Cir. 2019) ("'[T]he purpose and

flagrancy of the official misconduct' . . . 'is the most important

part of the analysis "because it is tied directly to the rationale

- 31 - underlying the exclusionary rule, deterrence of police

misconduct."'" (first quoting Cordero-Rosario, 786 F.3d at 76; and

then quoting United States v. Stark, 499 F.3d 72, 77 (1st Cir.

2007))).

According to Sergeant López-Maysonet's testimony, which

the district court credited, Officers Lopez Garcia and Garcia

Nieves, upon arriving at the site, exiting their vehicle, and

announcing themselves as law enforcement, chased several

individuals into the woods as other officers arrived. Sergeant

López-Maysonet "was behind Officer [Garcia Nieves] when [he]

noticed an individual that remained sitting down on a plastic

chair, so [Sergeant López-Maysonet] turned and . . . identified

[him]self as a police officer and the individual stood up facing

[him], . . . turned to the right and . . . opened [the bag he was

holding] and showed [López-Maysonet] the contents." To be sure,

the officers' cumulative show of force as they pursued the fleeing

individuals contributed to the seizure of Sierra-Ayala. But

chasing other fleeing individuals cannot be interpreted as

exploiting the illegal seizure to induce the seized individual to

surrender evidence. Cf. Wardlow, 528 U.S. at 124 (unprovoked

flight may provide reasonable suspicion to investigate fleeing

individuals). Nor was turning towards Sierra-Ayala and

identifying himself as a police officer while the other officers

pursued those in flight flagrant misconduct by Sergeant López-

- 32 - Maysonet. See Smith, 919 F.3d at 12 (distinguishing the

"professional and polite" interactions at issue from the "extreme

tactics the Supreme Court [has] deemed coercive").

Any number of scenarios could have followed Sergeant

López-Maysonet's identification of himself as law enforcement,

including an order from the sergeant to hand over the bag -- which

likely would have been deemed to exploit the initial seizure --

but also a notification that Sierra-Ayala was free to go -- which

clearly would not. But, as the district court found, nothing

exploitative happened: Sergeant López-Maysonet "just identified

himself, and [Sierra-Ayala] gave him the bag." These facts render

this case quite unlike Camacho, where we suppressed evidence under

the fruit-of-the-poisonous-tree doctrine after police officers

engaged in aggressive questioning of Camacho after an illegal stop

and "[t]he only intervening action by Camacho between the illegal

stop and the frisk [that precipitated the discovery of evidence]

was removing his hands from his pockets at [an officer]'s

direction." 661 F.3d at 729-30. Sierra-Ayala's intervening

volitional act, in the absence of exploitative behavior by López-

Maysonet, renders the discovery of the drugs sufficiently

attenuated so as to dissipate the taint of the initial unlawful

seizure. Hence, we affirm the district court's denial of Sierra-

Ayala's motion to suppress. See United States v. Rivera, 825 F.3d

59, 64 (1st Cir. 2016) ("[B]ecause of the de novo component to our

- 33 - review, we can affirm on any ground appearing in the

record . . . .").

III.

We now turn to appellant's appeal of the limitations the

district court imposed on the cross-examination of Sergeant López-

Maysonet.

The Confrontation Clause of the Sixth Amendment

"guarantees criminal defendants the right to cross-examine those

who testify against them." United States v. Jiménez-Bencevi, 788

F.3d 7, 20 (1st Cir. 2015) (quoting United States v. Vega Molina,

407 F.3d 511, 522 (1st Cir. 2005)). But this right is not

unlimited. Although it encompasses "the right to cross-examine

the government's witness about his bias against the defendant and

his motive for testifying," id. at 21 (quoting United States v.

Ofray–Campos, 534 F.3d 1, 36 (1st Cir. 2008)), trial judges may

circumscribe the extent of cross-examination, within "reasonable

limits[,] . . . based on concerns about . . . harassment,

prejudice, confusion of the issues, the witness'[s] safety, or

interrogation that is repetitive or only marginally relevant," id.

(quoting Delaware v. Van Arsdall, 475 U.S. 673, 679 (1986)).

Consequently, we review de novo properly preserved challenges to

a district court's decision as to whether a defendant had

"sufficient leeway to establish a reasonably complete picture of

- 34 - the witness'[s] veracity, bias, and motivation" despite the

limitations on cross-examination. United States v. Sandoval, 6

F.4th 63, 88 (1st Cir. 2021) (quoting Jiménez-Bencevi, 788 F.3d at

21). Provided this initial threshold is met, we review the

specific limitations imposed by the district court for abuse of

discretion. Jiménez-Bencevi, 788 F.3d at 21.

B. Discussion

Appellant does not contend that he was denied a

reasonable opportunity to impeach Sergeant López-Maysonet.

Instead, appellant argues that the district court abused its

discretion by preventing defense counsel from questioning Sergeant

López-Maysonet about the disciplinary incident involving Officer

López García, and about Sergeant López-Maysonet's testimony about

the incident at the suppression hearing. Because appellant objects

to a restriction on the manner or scope of cross-examination, our

review begins at the second stage of the Confrontation Clause

inquiry and we review the restrictions imposed by the court for

abuse of discretion. Appellant must show that the limitations on

cross-examination were "clearly prejudicial" to establish an abuse

of discretion. United States v. Rosario-Pérez, 957 F.3d 277, 297

(1st Cir. 2020) (quoting Ofray-Campos, 534 F.3d at 37). "The

ultimate question is whether 'the jury is provided with sufficient

information . . . to make a discriminating appraisal of a

- 35 - witness's motives and bias.'" Id. (quoting United States v.

Landrón-Class, 696 F.3d 62, 72 (1st Cir. 2012)).

Under Federal Rule of Evidence 608(b), "extrinsic

evidence is not admissible to prove specific instances of a

witness's conduct in order to attack or support the witness's

character for truthfulness," but the district court "may, on cross-

examination, allow them to be inquired into if they are probative

of the character for truthfulness or untruthfulness." The district

court precluded questioning about the administrative complaint

against Sergeant López-Maysonet because it found neither the fact

of the complaint nor López-Maysonet's answers at the suppression

hearing probative of his character for truthfulness or for his

bias. Even assuming that cross-examination on these issues would

be probative of Sergeant López-Maysonet's character for

truthfulness or bias, however, the district court's preclusion of

questioning was not clearly prejudicial to appellant because

defense counsel was able to impeach López-Maysonet's character for

truthfulness and bias17 by questioning him about inconsistencies

between his testimony and his incident report.18

17 Appellant's theory of Sergeant López-Maysonet's bias is that the existence of the administrative complaint about the late filing of a report gave him an incentive to lie during his testimony so as not to jeopardize his career. But, beyond this speculative assertion, appellant does not identify a connection between the administrative complaint and the sergeant's testimony in this case to support this theory of bias. 18 Specifically, defense counsel questioned Sergeant López-

- 36 - See United States v. Fortes, 619 F.2d 108, 118 (1st Cir. 1980)

("The court need not permit unending excursions into each and every

matter touching upon veracity if a reasonably complete picture has

already been developed."). Because appellant has not established

that the limits on cross-examination were clearly prejudicial, we

conclude that the district court did not abuse its discretion.

Affirmed.

Maysonet about why he did not list a holster among the items seized from Sierra-Ayala in the post-arrest inventory report. Defense counsel also asked Sergeant López-Maysonet about his failure to identify a twenty-five-cent coin in the inventory report.

- 37 -