United States v. Sierra-Ayala ( 2022 )

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.
A. Standard of Review
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 -