United States v. Villa-Guillen
U.S. Court of Appeals for the First Circuit
United States v. Villa-Guillen, 102 F.4th 508 (1st Cir. 2024)
United States v. Villa-Guillen
Opinion
United States Court of Appeals
For the First Circuit
No. 21-1545
UNITED STATES,
Appellee,
v.
RICARDO A. VILLA-GUILLEN,
Defendant, Appellant.
APPEAL FROM THE UNITED STATES DISTRICT COURT
FOR THE DISTRICT OF PUERTO RICO
[Hon. Francisco A. Besosa, U.S. District Judge]
Before
Rikelman, Hamilton,* and Thompson,
Circuit Judges.
Rachel Brill for appellant.
David C. Bornstein, Assistant United States Attorney, 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.
May 17, 2024
* Of the Seventh Circuit, sitting by designation.
RIKELMAN, Circuit Judge. After a short trial consisting
of almost no physical evidence, a jury convicted Ricardo
Villa-Guillen ("Villa") of conspiring to traffic cocaine from
Puerto Rico to the continental United States, in violation of 18
U.S.C. §§ 841(a)(1) and 846. On appeal, Villa alleges an array of
errors in the district court proceedings. We agree with Villa
that two of the district court's evidentiary rulings led to
prejudicial error. Those rulings involved types of evidence that
are likely to lead a jury astray -- the admission of a letter
discussing Villa's potential interest in a plea deal, which the
government claimed was tantamount to a confession, and the
admission of testimony suggesting that Villa was more likely to
have committed this crime because he had supposedly participated
in a different drug transaction (for which he was never charged).
We therefore reverse and order a new trial.
I. BACKGROUND
A. Relevant Facts
"Because we review the challenged evidentiary rulings
using a balanced approach, 'objectively viewing the evidence of
record,' we present the background facts in a similarly balanced
manner." United States v. Irizarry-Sisco, 87 F.4th 38, 41-42(1st Cir. 2023) (quoting United States v. Velazquez-Fontanez,6 F.4th 205, 212
(1st Cir. 2021)); accord Lech v. von Goeler,92 F.4th 56, 61
(1st Cir. 2024) (citation omitted). In recounting the facts,
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we draw from the testimony of the government's witnesses. See
Irizarry-Sisco, 87 F.4th at 42.
Villa began working as a cocaine courier or "mule" around
2005, after learning that his childhood friend, José
Herrera-Olavarría ("Herrera"), was part of a trafficking
organization run by Humberto Concepción-Andrades ("Concepción").
Concepción transported narcotics from Puerto Rico to New York,
relying on corrupt Transportation Security Agency and airline
employees who helped his couriers circumvent security screenings
to check suitcases containing cocaine onto commercial flights to
New York City.1 The couriers then boarded the same flights,
retrieved the suitcases at baggage claim upon arrival, and
transported the suitcases to designated hotels in the New York
area. Once at the hotels, couriers received instructions to
transfer the cocaine to distributors; couriers also would collect
money from prior sales, and one trial witness suggested that
sometimes couriers would travel to New York only to collect money,
not to deliver drugs. According to Herrera, between 2005 and 2007,
Villa acted as a courier in Concepción's operation seven or eight
times, five or six of which were in Herrera's presence.
1 On a trafficking day, Concepción would provide suitcases
filled with cocaine and tagged with U.S. Department of Agriculture
inspection stickers to the couriers near the airport.
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Around 2009, the start date of the conspiracy charged in
this case, Herrera took on a greater role in Concepción's operation
and began organizing cocaine shipments on Delta flights. Herrera
claimed that Villa was a courier on three of his shipments between
2009 and 2013. After arriving in New York, Villa would travel to
the destination hotel by taxi, usually driven by Harold Domínguez.2
By the time Villa completed those trips, he had served
as a courier about ten times, and the organization's leadership
required Villa to change roles out of concern he might otherwise
be recognized. Accordingly, Villa became a "watcher,"
recommending new couriers to the organization and keeping an eye
on them during their trips to New York. Herrera recounted that
Villa served as a watcher on two trips. In addition, Herrera
claimed, Villa invested his own money in five shipments, purchasing
one or two kilograms of cocaine in Puerto Rico and paying haulage
fees of $2,000 per kilogram for Herrera's couriers to transport
the cocaine to New York; Villa would then keep the profit on those
sales.
2 Domínguez began transporting Herrera's couriers around New
York in 2010. He received $400 for each trip.
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B. Legal Proceedings
In June 2017, a federal grand jury in the District of
Puerto Rico returned a superseding indictment charging Villa,
Concepción, Herrera, and five others with conspiracy to possess
with intent to distribute five kilograms or more of cocaine in
violation of 21 U.S.C. §§ 841(a)(1) and 846.3 The alleged
conspiracy took place from "2009 through December 2013," and
"included, but was not limited to," traveling or arranging travel
"on commercial flights that departed from the Luis Munoz-Marin
International Airport in Carolina, Puerto Rico to the continental
United States with kilograms of cocaine concealed inside
suitcases." The indictment also alleged that the conspirators
"mailed controlled substances to the continental United States."
Villa was arrested in July 2017 and ordered held without bail.
One after another, Villa's co-defendants struck plea
agreements, but after unsuccessful negotiations, Villa went to
trial. The government's trial evidence consisted of three days of
testimony from five witnesses, including Herrera and Domínguez.4
The only physical or documentary evidence the government
3 The first indictment had not named either Villa or
Concepción as defendants.
4Domínguez was not charged in the conspiracy but had entered
into a plea agreement and a cooperation agreement in connection
with separate federal charges.
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introduced were photographs: some identified several of Villa's
co-conspirators, one depicted money found during a collateral
incident, and several showed suitcases from another courier's
cocaine shipment that had been seized at John F. Kennedy (JFK)
Airport. Villa did not testify, nor did the defense put on other
evidence.
The government's first witness after opening statements
was Guillermo Salas, a paid Drug Enforcement Agency (DEA)
informant. Salas testified that Villa had tried to purchase eleven
kilograms of cocaine from him in a sham drug sale in March 2012
near Miami. After agreeing with Villa to the terms of the sale by
phone, Salas met Villa and two other men in the Miami area and
instructed Villa to follow him to a nearby warehouse to consummate
the transaction. A DEA task force tracked the convoy as it
traveled to the site of the ostensible deal, and after seeing Villa
make an illegal lane change, DEA agents pulled his vehicle over.
While a task-force agent spoke to Villa, a drug-detection dog
"alerted" to the passenger side of the vehicle, prompting a search
that produced two white plastic bags containing $296,014 wrapped
in "quick-count" bundles.5 The officers did not find cocaine in
5Guillermo Cuba, a police officer involved in the Florida
incident, testified that "quick-count" bundles of cash are
commonly used in "money laundering and drug trafficking." The
government's Exhibit 14 showed a photograph of the seized money.
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the vehicle and did not arrest Villa or his associates, nor was
Villa separately charged in connection with the incident.
Guillermo Cuba testified after Salas. Cuba, a Miami-Dade police
officer assigned to the DEA task force involved in the sting
operation, largely corroborated Salas's account of the Florida
incident (collectively, "the Florida testimony"). Villa objected
to all the Florida testimony, contending that it was irrelevant
and unfairly prejudicial. The district court overruled his
objections and denied post-trial motions based on those
objections.
Domínguez testified next, focusing on Villa's courier
activities between 2009 and 2012. Villa sought to cross-examine
Domínguez about statements he made to the grand jury that were
inconsistent with his trial testimony. But the district court
limited the scope of the cross-examination on the ground that it
would involve "impeachment by omission."
Next, Dustin Genco, a New York City police officer
assigned to a DEA Task Force, testified about the arrest at JFK
Airport in August 2010 of a courier named Mapula, who was carrying
fifteen kilograms of cocaine. (Herrera later testified that Villa
had invested in two of those kilograms of cocaine.) At the time,
Mapula was working as a mule to pay off a debt he owed Herrera for
losing three kilograms of cocaine while facilitating a previous
drug sale in New York. Genco also identified six government
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exhibits, which consisted of photographs of the suitcases from
which Mapula's cocaine had been seized. He offered no testimony
about Villa.
Herrera, the government's final witness, testified
across two days of trial. Herrera described the structure and
operations of the conspiracy and Villa's roles within it, including
that Villa had been a "mule," a "watcher," and an "investor" in
ten shipments of twenty to twenty-five kilograms of cocaine each.
At the close of its case, the government asked to read
into evidence a redacted version of a letter Villa had written to
the court seeking information about a pending motion. In the
letter, Villa stated that he "ha[d] expressed . . . [his] desire
to reach an agreement with the Government." Villa had continuously
objected under Federal Rule of Evidence 403 to the letter's
admission, but the district court overruled his objection. After
the letter was read to the jury, the court took judicial notice of
it and later instructed the jury on the meaning and effect of
judicial notice. Following approximately three hours of
deliberation, the jury found Villa guilty. The district court
sentenced Villa to 300 months' imprisonment and five years'
supervised release, and Villa timely appealed.
II. STANDARD OF REVIEW
We review preserved objections to a district court's
evidentiary rulings for abuse of discretion. United States v.
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Monteiro, 871 F.3d 99, 110(1st Cir. 2017). Although this standard of review affords latitude to the district court's judgment calls, it is "not a 'rubber stamp.'" Colón Cabrera v. Esso Standard Oil Co. (P.R.),723 F.3d 82, 88
(1st Cir. 2013) (quoting Negrón-Almeda v. Santiago,528 F.3d 15, 21
(1st Cir. 2008)). Rather, we must carefully examine the record to ascertain whether "a material factor deserving significant weight [was] ignored, . . . an improper factor [was] relied upon, or . . . all proper and no improper factors [were] assessed, but the court [made] a serious mistake in weighing them," including whether the district court made "[a]n error of law." Lech,92 F.4th at 63-64
(citations omitted). Even so, an "error does not require reversal if it was harmless," meaning "it can be said that the judgment was not substantially swayed by the error." United States v. Burgos-Montes,786 F.3d 92, 114
(1st Cir. 2015) (citation and
internal quotation marks omitted).
III. DISCUSSION
A. Villa's Letter to the Court
Right before it began its deliberations, the jury heard
about Villa's letter to the district court, which the government
described in its closing argument as tantamount to a confession.
Villa contends on appeal, as he vigorously insisted before the
district court, that the letter was inadmissible under Rule 403
because its minimal probative value was substantially outweighed
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by the risk of unfair prejudice. We agree and explain in detail
below why we conclude that the error in admitting the letter was
not harmless.
To put the letter in context, in 2019, Villa had filed
a suppression motion in a separate proceeding before the same
federal district court judge. Although a magistrate judge had
conducted a hearing on the motion and submitted a written
recommendation to the district court, several months had passed
without the district court entering an order on the motion.
Understandably, Villa was interested in the disposition of the
suppression motion, and he personally wrote to the court seeking
an update. He explained that he had a "desire to reach an agreement
with the Government" and hoped the court would rule promptly
because Villa would be "in the best disposition to make a fair,
reasonable and intelligent agreement once [he knew] the decision
about the Suppression of Evidence." The letter was filed on the
dockets of both this case and the other proceeding.
Villa nonetheless maintained his innocence of the
charges filed in this case and went to trial. The government
sought to introduce the letter shortly after trial began, and the
letter's admissibility became an intensely contested topic at
sidebar throughout trial. After multiple rounds of argument about
the letter's evidentiary value, the district court ultimately
decided to let the letter in. The court believed the letter was
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"relevant because Villa's assertions convey a consciousness of
guilt," and the court thought its admission was fair because Villa
sent the "incriminating letter to the Court on his own accord."
The court also noted that we had affirmed its ruling admitting
what it considered to be a similar letter in a different case,
although the earlier case did not involve a Rule 403 objection.
See United States v. Bauzó-Santiago, 867 F.3d 13, 21 (1st Cir.
2017).6
At the government's suggestion, the court admitted a
redacted version of Villa's letter, stripped of references to the
suppression motion, the other criminal proceeding, Villa's
pretrial detention, and discussions with Villa's attorney. The
version that was ultimately read aloud to the jury contained only
the bolded language below:
Honorable Judge Besosa
I extend the most cordial greetings to all the
personnel of the courtroom you so well
preside.
I am writing you this letter because I am going
through a bad time with a lot of frustration
amidst the legal proceedings I am facing.
I respectfully and heartily request the
notification of the decision made regarding
6 The appellant in Bauzó-Santiago had offered "no 403-based
argument . . . on appeal," so we lacked occasion to decide whether
the letter in that case should have been excluded on the grounds
Villa now asks us to consider. 867 F.3d at 21.
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the Suppression Hearing held last December 21,
2018 and February 20, 2019. Case No. 17-608.
In many occasions, I have expressed to my
legal representation my desire to reach an
agreement with the Government. I am in the
best disposition to make a fair, reasonable
and intelligent agreement once I know the
decision about the Suppression of Evidence to
agree and take the best decision regarding the
same. Case No. 16-526.
Thank you for your usual[] attention,
Cordially,
Ricardo Villa Guillen
[signature]
50384-069
MDC Guaynabo[.]
Thus, as redacted, the letter focused on Villa's "desire to reach
an agreement with the Government."
The government read the redacted letter into evidence,
after which the court took judicial notice of its contents. The
court then explained the meaning and effect of judicial notice by
reading the jury instruction it had prepared in accordance with
Federal Rule of Evidence 201(f).7 The instruction stated:
I believe that the contents of the letter the
Defendant sent to the Court, which I read to
7 "In a criminal case," a court taking judicial notice of an
adjudicative fact "must instruct the jury that it may or may not
accept the noticed fact as conclusive." Fed. R. Evid. 201(f).
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you,[8] can be so accurately and readily
determined that it cannot be reasonably
disputed. You may, therefore, reasonably
treat this fact as proven, even though no
other evidence has been presented on this
point.
As with any fact, however, the final decision
whether or not to accept it is for you to
decide. You are not required to agree with
me.
The ruling admitting the letter falls among the "rare
and 'extraordinarily compelling circumstances'" where we conclude
that we must reverse the district court's judgment about the
outcome of the balancing test under Rule 403. United States v.
Gonyer, 761 F.3d 157, 164(1st Cir. 2014) (citation omitted). We begin with the letter's minimal probative value. It is of course black-letter law that the threshold for relevance "is low, and it permits the introduction of evidence that 'has any tendency to make a fact more or less probable.'" Ward v. Schaefer,91 F.4th 538, 544-45
(1st Cir. 2024) (quoting Fed. R. Evid. 401). Yet even
against this permissive standard, we struggle to see the relevance
of Villa's interest in reaching a plea agreement to the question
of whether he was in fact guilty of trafficking narcotics as part
of the charged conspiracy.
8 The government, not the court, read the letter, but we have
reproduced the wording provided to the jury.
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To start, we reject the government's contention that
Villa's bare interest in a possible plea agreement is relevant to
establishing his guilt. "[T]here are a number of reasons why a
defendant might choose to plead guilty." Thore v. Howe, 466 F.3d
173, 185(1st Cir. 2006). Indeed, "a defendant's decision to plead guilty may have any number of other motivations" aside from consciousness of guilt, "including shock, avoidance of financial and emotional cost, and hope for a lesser sentence."Id.
(quoting Haring v. Prosise,462 U.S. 306, 318-19
(1983)). Our precedent has sensibly applied this principle. For example, when a defendant enters a "knowing, intelligent and voluntary" guilty plea that otherwise complies with the requirements of Rule 11 of the Federal Rules of Criminal Procedure, he may still later withdraw that plea if he presents previously unavailable evidence indicating that he "might actually be innocent." United States v. Newbert,504 F.3d 180, 183, 187
(1st Cir. 2007); see also United States v. Fonseca,49 F.4th 1, 7
(1st Cir. 2022) (recognizing that defendants may withdraw knowing, voluntary pleas based on a "serious claim of actual innocence" (citation omitted)). In other words, federal law acknowledges that an innocent defendant might nevertheless plead guilty. An initial plea is "not dispositive of [a defendant's] guilt." Newbert,504 F.3d at 187
n.5.
If an innocent defendant might plead guilty, then the
same defendant might logically explore the possibility of striking
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a bargain with the government. We can easily conceive of sensible
reasons for doing so. For instance, although "[g]uilty defendants
generally know that they are guilty, and are aware of the likely
evidence against them," innocent defendants might engage in plea
discussions because they lack "information about the state's
evidence," making it difficult for the innocent to "forecast the
likely trial outcome." Stephanos Bibas, Plea Bargaining Outside
the Shadow of Trial, 117 Harv. L. Rev. 2463, 2493-94 (2004). Such a defendant, despite his innocence, might prefer the certainty of a plea deal over "the risk of [a] high statutory sentence[]" if he is convicted after a trial. Rachel E. Barkow, Separation of Powers and the Criminal Law,58 Stan. L. Rev. 989
, 1034 (2006); cf. Blackledge v. Allison,431 U.S. 63, 71
(1977) (recognizing that by pleading guilty, a "defendant avoids . . . the anxieties and uncertainties of a trial"). Thus, we agree that "the fact that [a defendant] sought to engage in plea negotiations . . . is no more indicative of guilt than [of] a desire to pre-empt prosecution or to limit his exposure to a lengthy sentence." United States v. Gotti,457 F. Supp. 2d 395, 402
(S.D.N.Y. 2006). Absent "any detailed admission of criminal conduct," the "vague" interest in a possible plea deal reflected in Villa's letter is at best marginally probative of Villa's guilt as to the charged conspiracy.Id.
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Even if the letter had some probative value, however,
Rule 403 contemplates that evidence may still be excluded "if its
probative value is substantially outweighed by a danger
of . . . unfair prejudice." United States v. García-Sierra, 994
F.3d 17, 32(1st Cir. 2021) (quoting Fed. R. Evid. 403). Because "by design, all evidence is meant to be prejudicial," a district court's rulings under Rule 403 must avoid "only 'unfair' prejudice." United States v. Morales-Aldahondo,524 F.3d 115, 119-20
(1st Cir. 2008) (quoting United States v. Varoudakis,233 F.3d 113, 122
(1st Cir. 2000)). Still, even "concededly relevant evidence" should be excluded if it would otherwise "lure the factfinder into declaring guilt on a ground different from proof specific to the offense charged." García-Sierra,994 F.3d at 33
(quoting United States v. DiRosa,761 F.3d 144, 153
(1st Cir. 2014)); see also Old Chief v. United States,519 U.S. 172, 180
(1997) (same).
Here, the prejudice side of the Rule 403 scale weighed
decisively against admission, particularly given the government's
framing of the letter as a confession. The unduly prejudicial
effect begins with the letter's contents. In redacted form, the
letter read: "I am writing you this letter . . . amidst the legal
proceedings I am facing. . . . In [sic] many occasions, I have
expressed . . . my desire to reach an agreement with the
Government." Thus, the redacted letter excluded Villa's opening
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request for an update on the suppression motion and necessarily
skewed the jury's perception of Villa's purpose in sending the
letter in the first place.
To make things worse, by obscuring many other details in
the letter, the redactions further highlighted Villa's potential
interest in a plea. These redactions are the polar opposite of
the redactions we approved in the letter at issue in
Bauzó-Santiago. There, a defendant had penned a letter to the
court explicitly indicating that he "accepted [his] responsibility
as to guilt," and the letter was "redacted to remove any reference
to plea bargaining" before it was presented to the jury. 867 F.3d
at 17(emphasis added). As we explained, the jury could then infer guilt "from [the defendant's] admission to the charged crime," not "simply from his interest in pleading guilty."Id.
at 21 n.4. The redactions here accomplished the reverse: They encouraged the jury to infer guilt from Villa's interest in a plea agreement. And nowhere in Villa's letter -- redacted or not -- was there the type of explicit acceptance of guilt or admission to the charged crime that was crucial to our analysis in Bauzó-Santiago. Cf.id. at 16, 21-22
.
The government offers two responses. First, the
government contends that Villa never objected to the redactions.
We disagree. Throughout the proceedings, Villa objected to the
introduction of the letter in any form (with or without the
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redactions). Second, the government argues that the redactions
were made in an effort to respond to Villa's concern that the
unredacted letter was unduly prejudicial because of its references
to another case, Case 17-608. But as Villa points out, that simply
suggests that even an unredacted version of the letter should have
been excluded under Rule 403.
Additionally, the "prejudice and confusion was not
mitigated by the instructions provided to the jury."
García-Sierra, 994 F.3d at 32. To the contrary, the district
court's instruction on judicial notice compounded the unfairness
to Villa. As a reminder, after the government read the redacted
letter to the jury, the district court took judicial notice of it
(at the government's request). The court then explained to the
jury how it should understand the taking of judicial notice by
reading the instruction it planned to give, which stated, in
relevant part:
I believe that the contents of the letter the
Defendant sent to the Court, which I read to
you, can be so accurately and readily
determined that it cannot be reasonably
disputed. You may, therefore, reasonably
treat this fact as proven, even though no
other evidence has been presented on this
point.
As with any fact, however, the final decision
whether or not to accept it is for you to
decide. You are not required to agree with
me.
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(Emphases added.) The court's wording was a far cry from judicial
notice of the mere fact that a defendant's letter "was entered on
the district court's docket as entry ninety-four," which we upheld
in Bauzó-Santiago. 867 F.3d at 23(emphasizing that the noticed fact was "the letter's docketing"). Rather, the court's explanation "reasonably [could have] be[en] understood as an instruction that the contents of the letter [we]re true" rather than the mere fact that "the judge believed the letter was filed on the docket."Id. at 22-23
(emphasis added); cf. United States v. Watson,695 F.3d 159, 165
(1st Cir. 2012) (affirming judicial
notice over Rule 403 objection where the notice was "narrowly
confined to the material necessary for" the jury to understand the
noticed fact). And the jury heard that instruction not once, but
twice: immediately after the government introduced the letter, and
then again during the court's formal reading of all the
instructions.
The district court, for its part, agreed that the letter
did not establish Villa's legal culpability, noting at sidebar
that if the letter "were an admission or a conf[es]sion, I wouldn't
allow it." Yet the government asked the jury to draw precisely
that prejudicial inference from the letter. Cf. Watson, 695 F.3d
at 165 (finding no unfair prejudice where "the judge explicitly
forbade the government from intimating" an inflammatory
inference). In its closing argument, the government explained
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that the letter was "an admission," and tantamount to "the
Defendant saying, 'I admit to what I have done, and I am in the
best position to come to an agreement with the Government in
regards to what I have done.'"
We thus agree with Villa that the district court's
instruction combined with the government's argument indicated that
the "natural and intuitive" inference to draw from the letter was
that Villa's interest in a plea agreement meant he was guilty.
García-Sierra, 994 F.3d at 34. The jury should not have been "permitted to draw the inference of . . . guilt from the fact that," at the time he wrote the letter, Villa desired to "engage[] in plea discussions." Gotti,457 F. Supp. 2d at 402
. Because the
letter's de minimis probative value was substantially outweighed
by the unfairly prejudicial effect of its contents, particularly
in light of the redactions, we conclude that its admission was an
abuse of discretion.
Finally, we cannot agree that the introduction of the
letter was harmless. "An error will be treated as harmless only
if it is 'highly probable' that the error did not contribute to
the verdict." United States v. Kilmartin, 944 F.3d 315, 338 (1st
Cir. 2019) (citation omitted). This "case-specific inquiry"
directs us to consider "the centrality of the tainted material,
its uniqueness, its prejudicial impact, the uses to which it was
put during the trial, the relative strengths of the parties' cases,
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and any telltales that furnish clues to the likelihood that the
error affected the factfinder's resolution of a material issue."
Id.(quoting United States v. Piper,298 F.3d 47, 57
(1st Cir.
2002)).
Here those factors all point to prejudice. Villa's
defense throughout trial was that Herrera and Domínguez were lying
about his involvement to curry favor with the government in the
disposition of their own criminal troubles. And the government
relied on the letter in its closing argument to rebut exactly this
defense, arguing that the letter "corroborated the testimony of
Harold Dom[í]nguez and Jose Herrera" about Villa's role in the
conspiracy. By the government's own framing, the evidence on this
point was not "overwhelming." United States v. Ford, 839 F.3d 94,
110(1st Cir. 2016). And the government was right on that score. It pointed to only one other piece of evidence for corroboration: Mapula's arrest at JFK, transporting a shipment that included two kilograms of cocaine in which Villa allegedly had invested. But it was Herrera who connected Mapula to Villa by testifying that Villa was an investor in that shipment. The government did not present to the jury any physical evidence -- airline tickets, hotel reservations, cell phone records, seized drugs, or anything else -- tying Villa to the conspiracy. Cf. United States v. Colon,744 F.3d 752, 759
(1st Cir. 2014) (holding that any instructional
error relating to confession was harmless, in part because
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confession was "buttressed by physical evidence"). The letter,
accordingly, was the only evidence wholly independent of Villa's
alleged co-conspirators' testimony.9
What's more, the government, faced with multiple options
for how to present the letter to the jury in closing, chose to
style the letter as a confession, enhancing the prejudicial nature
of the letter in two important ways. First, the "presentation of
improper material at the end of trial 'magnifie[s]' its prejudicial
effect because it is 'freshest in the mind of the jury when [it]
retire[s] to deliberate.'"10 Zapata v. Vasquez, 788 F.3d 1106,
1122(9th Cir. 2015) (alterations in original) (citation omitted). Second, and more fundamentally, the government invoked the unique power of confessions to influence a jury's perception of a defendant's culpability. A defendant's confession is "probably the most probative and damaging evidence that can be admitted against him[,] . . . so much so that we may justifiably doubt [the jury's] ability to put [it] out of mind even if told to do so." Arizona v. Fulminante,499 U.S. 279, 296
(1991) (quoting Bruton v.
9As we will explain momentarily, the testimony from Guillermo
Salas and Guillermo Cuba pertaining to events in Florida also
should have been excluded, and our assessment of the letter's
harmfulness is restricted to the "properly admitted evidence"
against Villa. Kilmartin, 944 F.3d at 338.
10 In addition to featuring in the government's closing
argument, the letter also was the last evidence admitted before
the jury received its instructions.
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United States, 391 U.S. 123, 139-40(1968) (White, J., dissenting)). Thus, we have previously explained that "by nature," confessions are "likely to be at the center of a jury's attention." United States v. Leon-Delfis,203 F.3d 103, 112
(1st Cir. 2000).
In light of that uniquely forceful effect, we cannot say it is
"highly probable" that the inflammatory and misleading letter "did
not substantially sway the jury." Kilmartin, 477 F.3d at 338
(citation omitted). Villa is entitled to a trial untainted by its
effect.
B. The Florida Testimony
Whereas the letter was the last piece of evidence the
government presented to the jury, the trial began with testimony
about a sting operation involving Villa in Florida. Villa contends
that this testimony also should have been excluded by the district
court. He argues that the letter and the Florida testimony, which
he describes as the two "bookends" of the trial, rendered his trial
unfair.
Villa insists on appeal that the Florida testimony
should have been excluded as either wholly irrelevant under Rule
401 or as unfairly prejudicial under Rule 403. According to Villa,
the Florida testimony involved events that took place outside of
the charged conspiracy, and the government elicited the testimony
solely to invite the jury to make an unfairly prejudicial
propensity inference: that Villa's involvement in the Florida
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events made it more likely he participated in the trafficking of
cocaine from Puerto Rico to New York. For its part, the government
insists that the testimony was relevant because the Florida
incident was part of the charged conspiracy, or in the alternative
(and in line with the district court's reasoning below), because
it was probative of Villa's knowledge or intent related to the
cocaine trafficking charge. Because Villa adequately objected,
our review is for abuse of discretion.11
11The government contends that we should review this issue
for plain error because Villa's counsel allegedly did not preserve
this claim by failing to object below. We, however, view the
record differently. Villa's counsel objected on relevance grounds
as soon as Salas (the government's first witness) started
testifying, stating "objection as to relevance . . . 401." We
agree with the government that this objection did not preserve the
Rule 403 argument Villa presents on appeal. See, e.g., United
States v. Iwuala, 789 F.3d 1, 7 (1st Cir. 2015). But Villa offered
a more specific objection as soon as Salas began to testify about
the traffic stop, reiterating that there had been no "information"
suggesting that the Florida incident was "related in any fashion
to the" charges he faced at trial, before the district court
interposed a question. The district court understood and addressed
Villa's trial and post-trial objections to the Florida testimony
as raising a Rule 403 challenge, and so do we.
Although propensity evidence is often challenged under
Federal Rule of Evidence 404(b), Villa made no objection under
that rule at trial or on appeal, and he confirmed as much at oral
argument before us. Accordingly, we review Villa's propensity
arguments under Rule 403, but not under Rule 404. Nevertheless,
we agree with Villa that we may review through a Rule 403 lens
whether the district court abused its discretion by understating
the risk that the jury would infer criminal propensity from the
Florida testimony. We have long and often considered whether
other-act evidence must be excluded under Rule 403, despite having
at least a scintilla of probative value for a non-propensity
- 24 -
As before, we begin by evaluating the evidence's
probative value. At trial, the government contended that the
Florida incident was part of the charged conspiracy and was
therefore relevant to proving its existence. According to the
government and the district court, the Florida incident occurred
"during the timeframe of the conspiracy" charged in the indictment,
which did not "restrict the scope of the conspiracy to the
transportation of cocaine from Puerto Rico to New York."
The government's arguments about the scope of the
indictment do not stand up. When analyzing whether a particular
event was part of a charged conspiracy, we look to the "temporal
proximity and factual similarity" between the event and the
conspiracy described in the indictment,12 including by analyzing
whether the incident employed similar "means" in service of a
purpose under Rule 404(b), because of a risk that the permissible
relevance of the evidence would still "lur[e]" the jury "into
forbidden propensity reasoning." García-Sierra, 994 F.3d at 33; see also Varoudakis,233 F.3d at 122
; 22A Charles Alan Wright &
Arthur R. Miller, Federal Practice and Procedure § 5259 (noting
that "appellate judges can still reverse by finding [the] trial
judge abused [their] discretion" in evaluating the propensity risk
of other-act evidence under Rule 403).
12 Our case law has sometimes phrased the analysis as
evaluating "the remoteness in time of the other act and the degree
of resemblance to the crime charged" as part of the Rule 403
analysis of the probative value of prior bad acts when evidence of
that act is admitted for a proper purpose. See, e.g., Varoudakis,
233 F.3d at 119(quoting United States v. Frankhauser,80 F.3d 641, 648
(1st Cir. 1996)).
- 25 -
similar "purpose" as the charged offense. United States v.
Escobar-de Jesus, 187 F.3d 148, 168(1st Cir. 1999). Although the Florida incident fell within the general timeframe of the indictment and arguably shared a common "purpose" related to illegal trafficking in cocaine, it plainly involved entirely different "means." The indictment identifies only two means of transporting cocaine "to the continental United States": The conspirators (1) "traveled on commercial flights that departed from the Luis Munoz-Marin International Airport in Carolina, Puerto Rico [to the continental United States] . . . with kilograms of cocaine concealed inside suitcases," and (2) "mailed controlled substances to," as opposed to within, "the continental United States." (Emphases added.) Neither description encompasses the facts underlying the Florida incident, i.e., an attempt by Villa alone, without any apparent involvement by anyone in the Concepción organization, to purchase cocaine within the continental United States. Cf. Escobar-de Jesus,187 F.3d at 168
(affirming that an incident was relevant "as an additional overt
act within the conspiracy charged" because the incident "stemmed
from the same conspiratorial agreement to import and distribute
cocaine").
The testimony is not spared, as the government contends,
by the fact that the indictment merely stated that the conspiracy's
means "included, but w[ere] not limited to" mailing or transporting
- 26 -
cocaine from Puerto Rico to the continental United States on
commercial aircraft. The government points to no trial evidence
(nor could we find any) that "connected" the Florida testimony to
the conspiracy charged in the indictment other than Villa's mere
presence. United States v. Lynn, 856 F.2d 430, 435(1st Cir. 1988) (reversing district court where the government failed to show prior bad act was part of "a continuing or connected scheme of marijuana importation on the part of the defendant"). Neither Herrera nor Domínguez testified that any of the narcotics trafficked, whether by mail or by commercial air carrier, originated in Florida, and neither Salas nor Cuba testified about the intended destination of the cocaine Salas purported to sell to Villa. Further, other than Villa, the "participants in both events were entirely different," and there is no evidence any other co-defendant was involved in the Florida incident. Id.; cf. United States v. Robles-Alvarez,874 F.3d 46, 50-51
(1st Cir. 2017) (concluding that evidence of
defendant's participation in drug-trafficking incident was part of
the charged conspiracy because it involved, inter alia, all of the
same co-conspirators). As Villa points out, none of the
participants in the Florida events (other than himself) were
indicted in this case. Villa's position is also supported by the
government's characterization in its opening statement of the
Concepción conspiracy as a "large drug conspiracy that was involved
- 27 -
in shipping large quantities, extremely large quantities[,] of
kilograms of cocaine from Puerto Rico to New York."
Turning to the government's alternative argument that
the Florida incident demonstrated Villa's intent, it is true that
the Florida testimony, if believed by the jury, suggested that
Villa was prepared to consummate a drug transaction. And the
district court defended the admission of the testimony on the
ground that it was "probative of [Villa's] intent both to invest
in cocaine, and actually distribute it." Yet we conclude "the
probative worth of [the Florida incident] toward proving [Villa's]
intent to commit the instant offense is difficult to
conceptualize," absent a propensity inference. Lynn, 856 F.2d at
436. In any event, the government had other avenues of proving
intent without the Florida incident because the jury could have
"believe[d] the testimony of" Herrera, who testified that he and
Villa had worked as couriers together between 2005 and 2007.13
Villa separately argues on appeal that Herrera's testimony
13
concerning his and Villa's trafficking activities between 2005 and
2007 also should have been excluded as propensity evidence. But
we have held that earlier illegal conduct involving the same
co-conspirators is "relevant . . . [to] the background of the
illegal relationship." United States v. Flemmi, 402 F.3d 79, 89(1st Cir. 1999); see also Robles-Alvarez,874 F.3d at 51
(explaining that earlier criminal conduct may be relevant to how
the "co-conspirators came together" and why the leader "trusted
[the defendant] and decided to go into business with [him]"). And
Villa offers no reason to think that testimony was otherwise
unfairly prejudicial if used for that purpose.
- 28 -
Id.; cf. United States v. Crocker, 788 F.2d 802, 804(1st Cir. 1986) (holding that defendant's prior criminal involvement with identical co-conspirator was admissible because it was probative of defendant's intent in the charged crime). In light of Herrera's account, the Florida testimony was "cumulative" and, therefore, of lesser probative value than it otherwise might have been. Kilmartin,944 F.3d at 337
.
Whereas the probative value of the Florida testimony was
slight, its potential for unfair prejudice was great. "The term
'unfair prejudice,' as to a criminal defendant, speaks to the
capacity of some concededly relevant evidence to lure the
factfinder into declaring guilt on a ground different from proof
specific to the offense charged." Old Chief, 519 U.S. at 180. "Such improper grounds" justifying exclusion under Rule 403 include "generalizing a defendant's earlier bad act into bad character and taking that as raising the odds that he did the later bad act now charged (or, worse, as calling for preventive conviction even if he should happen to be innocent momentarily)."Id. at 180-81
. Thus, "[t]he overriding policy of excluding [propensity] evidence, despite its admitted probative value, is the practical experience that its disallowance tends to prevent confusion of the issues, unfair surprise and undue prejudice."Id.
at 181 (quoting Michaelson v. United States,335 U.S. 469, 475-76
(1948)).
- 29 -
Here, as in Lynn, the "ordinary inference" for the jury
to draw from the Florida testimony "would seem very close to the
[propensity] inference" that our precedents find so unfairly
prejudicial. 856 F.2d at 436. Salas testified almost immediately after the government's opening statement, which made no reference to Florida and characterized the conspiracy as involving trafficking cocaine only from Puerto Rico to New York in suitcases. The jury then heard from Salas and Cuba without any indication that the Florida events were part of the conspiracy. At that point, the reasonable inference for the jury was that Villa had a propensity for trafficking narcotics. The district court thus abused its discretion by fallowing testimony that "added virtually nothing of legitimate value to the government's case" while "fanning the flames of unfair prejudice." Kilmartin,944 F.3d at 337
.
Turning to prejudice, we again conclude that the
admission of this evidence was not harmless. Because the Florida
testimony was the only evidence independent of the co-conspirator
testimony (other than the unfairly prejudicial letter), we cannot
say with any "degree of assurance that" it "did not substantially
sway the jury." Id. at 338(citation omitted). This is especially true when the Florida incident was the only topic on which two of the government's five witnesses testified, and the government emphasized the testimony in its closing. Seeid. at 340
(finding
- 30 -
error was not harmless where a "full quarter of the government's
witnesses" provided unfairly prejudicial testimony and the
"prosecutor's summation made abundant use" of the evidence). Thus,
we order a new trial.14
C. Cross-Examination of Domínguez
Villa has identified one more troubling issue in the
proceedings below. He contends that the district court abused its
discretion by restricting cross-examination of Domínguez about
whether Villa was transporting drugs on the occasions they
interacted.
At trial, Domínguez testified that Villa traveled to
Puerto Rico to deliver drugs "four or five times," that Villa
participated in a discussion about how to address Mapula's missing
money, and that other mules told him that Villa had traveled with
them carrying drugs. But in 2016, Domínguez told the grand jury
that he picked up Villa only once, and that Villa "didn't come as
a mule. He came to pick money up."
Despite multiple requests by Villa's counsel, the
district court would not allow cross-examination about whether
Domínguez's trial and grand jury testimony were inconsistent as to
14Because we conclude that the Florida testimony should have
been excluded, we need not reach Villa's arguments that the
district court erred by failing to provide the jury with
multiple-conspiracy and paid-informant instructions.
- 31 -
whether Domínguez ever picked up Villa carrying narcotics, ruling
that to do so would be impermissible impeachment "by omission."
Instead, the district court permitted Villa to question Domínguez
about whether Villa "was sent . . . to get some money," but not to
"ask him whether that means that he didn't bring any drugs, because
that's impeachment by omission." Villa was barred, in the district
court's words, from cross-examining Domínguez "about things that
he did not say in the Grand Jury."
Before we turn to the legal standard for impeachment by
omission, however, we pause to note that the dispute here was not
about an omission at all. To be sure, impeachment by omission
occurs when a party seeks to impeach a witness's trial testimony
through evidence of their "previous failure to state a fact in
circumstances in which that fact naturally would have been
asserted." Jenkins v. Anderson, 447 U.S. 231, 239(1980); accord United States v. Meserve,271 F.3d 314, 320-21
(1st Cir. 2001)
(citation omitted). But the transcript of Domínguez's grand jury
testimony makes apparent that Domínguez contradicted himself at
trial on the precise issue that Villa was attempting to highlight
through cross-examination. Villa sought to impeach Domínguez with
Domínguez's grand jury testimony that Domínguez had picked up Villa
"only once. [Villa] didn't come as a mule. He came to pick money
up." In context, the express statement that Villa "didn't come as
a mule," before immediately stating that Villa "came to pick money
- 32 -
up," was obviously meant to convey that Villa had not come with
drugs. And if there was any doubt, the government immediately
confirmed at the grand jury: "Okay so he didn't bring drugs from
Puerto Rico to New York. He brought money from New York to Puerto
Rico?" "Exactly," said Domínguez. Because Domínguez testified
directly to this point (money versus drugs), there was no reason
to invoke the impeachment-by-omission framework. The necessary
analysis under Federal Rule of Evidence 613 merely required an
assessment of whether the grand jury testimony was inconsistent
with what Domínguez had said on the stand, and because the grand
jury testimony was "'irreconcilably at odds' with the [statement]
made at trial," impeachment on that ground was proper. United
States v. Ramos-Baez, 86 F.4th 28, 58(1st Cir. 2023) (citation omitted); see also United States v. Torres-Colón,790 F.3d 26
, 30
n.2 (1st Cir. 2015) (explaining that a prior statement need "not
be directly contradictory in order to be deemed inconsistent"
(citation omitted)).
Even if we set aside the omission/not-omission dispute,
we still cannot affirm the district court's ruling limiting the
cross-examination. "Common law traditionally . . . allowed
witnesses to be impeached by their previous failure to state a
fact in circumstances in which that fact naturally would have been
asserted." Jenkins, 447 U.S. at 239. Thus, we have held that
when "[p]rior statements . . . omit details included in a
- 33 -
witness's trial testimony," the question of whether the omission
creates an inconsistency with trial testimony turns on whether "it
would have been 'natural' for the witness to include the details
in the earlier statement." Meserve, 271 F.3d at 320-21 (quoting United States v. Stock,948 F.2d 1299, 1301
(D.C. Cir. 1991)); accord Ramos-Baez,86 F.4th at 58
(citation omitted). Whether it was "natural" hinges "on the 'nuances of the prior statement's context, as well as [the witness's] own loquacity.'" Meserve,271 F.3d at 321
(alteration in original) (quoting Stock,948 F.2d at 1301
). Naturalness may also turn on the importance of the details elicited at trial that were omitted in the earlier statement: It is more natural to omit "peripheral" details than to omit details pertaining to "core issue[s]." United States v. Catalán-Roman,585 F.3d 453
, 467-68 (1st Cir. 2009) (opinion of Lipez, J.) (quoting Meserve,271 F.3d at 321
).
At sidebar on the government's objection, the district
court ruled categorically that "you cannot impeach by omission."
In so ruling, the court never analyzed whether any "omission" by
Domínguez was natural in the context of his grand jury testimony.
Thus, the district court interpreted the Rule 613(a) standard as
erecting an absolute bar to impeachment by omission. As we have
explained, that position is contrary to common law tradition and
our precedent. See Jenkins, 447 U.S. at 239; Meserve,271 F.3d at 320-21
.
- 34 -
The district court recognized the error in its
categorical approach at sidebar in its later order denying Villa's
request for a new trial on this ground, concluding "the Court did
not abuse its discretion in proscribing Villa's attempt to impeach
by omission." The court reasoned that "[t]he question" Domínguez
was asked by the government before the grand jury -- "how do you
know [Villa]?" -- "d[id] not call for an exhaustive account of
every encounter between Domínguez and Villa."
Although correcting its earlier ruling that impeachment
by omission is never permissible, the district court still did not
apply the naturalness inquiry consistent with our case law. The
district court focused solely on the question posed by the
government, when Meserve directs courts to analyze whether the
"prior statement's context" means it "would have been 'natural'
for the witness to include the details in the earlier statement."
271 F.3d at 321 (emphases added) (citations omitted). In an
analysis focused on the naturalness of a "statement," the district
court should analyze both the question and the statement itself.
We also note that, during the grand jury proceedings,
the government asked Domínguez no fewer than four questions
relevant to the naturalness inquiry, but the district court
analyzed only one of them. The relevant back-and-forth before the
grand jury was prompted by the following question from the
government: "Can you name the different mules that you have picked
- 35 -
up during the period of time [covered by the indictment]?" After
Domínguez agreed, the prosecutor specified that "when you mention
the mule[,] if you can mention approximately how many trips you
have been [sic] picked them up at the airport." One page of
material following that question, which we assume contained
questions and testimony about other couriers, is redacted from the
grand jury transcript. The government then asked:
Government: How about [Villa]?
Domínguez: [Villa], only once. He didn't
come as a mule. He came to
pick money up.
Government: Okay so he didn't bring drugs
from Puerto Rico to New York.
He brought money from New York
to Puerto Rico?
Domínguez: Exactly.
(Emphases added.) Then, the government showed Domínguez a photo
of Villa, and asked:
Government: Do you recognize that person?
Domínguez: Yes, sir.
Government: Who is that?
Domínguez: That is [Villa].
Government: How do you know [Villa]?
Domínguez: He was sent as a mule to get
some money.
Government: Do you remember on how many
occasions?
Domínguez: Approximately only once.
- 36 -
Government: And who sent him?
Domínguez: [Herrera] did.
Government: To pick up money related to the
distribution of narcotics?
Domínguez: Yes, sir.
(Emphases added.)
The full context of Domínguez's prior statement
clarifies that the government's questions could well have invited
the purportedly omitted testimony. See Meserve, 271 F.3d at 321. The colloquy began with the government's request for information about how many times Domínguez had picked up "different mules." When asked about Villa, Domínguez answered, "only once." But because the government had asked about picking up "mules," Domínguez clarified (voluntarily) that Villa "didn't come as a mule"; he "came to pick money up." To the extent this statement was an omission at all, the detail it omitted was the fact that Villa did not come to deliver drugs; a mule delivers drugs, and as Domínguez explained, Villa didn't "come as a mule." The government understood it that way, confirming: "Okay so he didn't bring drugs from Puerto Rico to New York. He brought money from New York to Puerto Rico?" To which Domínguez replied: "Exactly." Cf.id.
(finding no abuse of discretion in restricting impeachment by
omission because witness "was not asked" about the omitted details
before the grand jury). Thus, aware that Domínguez had implied
that Villa had never traveled from Puerto Rico to New York to
- 37 -
deliver drugs, the prosecutor sought explicit confirmation of
precisely that fact.
The question of whether Villa had ever brought drugs to
New York was material to contested issues, not "peripheral" like
the omitted grand jury testimony in Meserve. 271 F.3d at 321.
The omission went not only to Domínguez's credibility but also to
Villa's criminal liability and to facts that would drive his
sentence. See Catalán-Roman, 585 F.3d at 467-68 (opinion of Lipez,
J.) (arguing it was an abuse of discretion to restrict impeachment
by omission that implicated an element of the offense and the
availability of capital punishment). Indeed, Domínguez's
testimony provided the only corroboration for Herrera's
description of Villa's travel to New York on three occasions as a
courier, and one or two as a "watcher." And the district court,
in turn, relied on Domínguez's and Herrera's testimony in its
drug-quantity calculation at sentencing. With Domínguez already
on the stand and his material omission laid bare in the transcript
of the grand jury proceeding, the district court abused its
discretion by limiting his cross-examination; the "significance of
[any] omissions was a jury issue." Id. at 468; see also id. at
477 (opinion of Boudin and Stahl, JJ.) ("Typically, latitude is
allowed in cross-examining the witness already on the stand whose
reactions may be grist for the jury.").
- 38 -
The government contends that any error here was harmless
because Domínguez had agreed before the grand jury that Villa
"didn't bring drugs from Puerto Rico to New York. He brought money
from New York to Puerto Rico." Because that statement contained
no omission, the argument goes, it was outside of the district
court's ruling on the objection, and so Villa should have impeached
Domínguez with it after the sidebar. See Moreno-Morales v. United
States, 334 F.3d 140, 148 (1st Cir. 2003) (holding that defendant
was not prejudiced where he had "ample evidence of a witness's
story changing over time, but chose not to utilize it"). The flaw
in the government's position is that the statement Villa sought to
impeach with -- that he "didn't come as a mule" -- also was not a
true omission, yet the district court prohibited Villa from
pursuing his cross-examination under the auspices of Meserve. The
transcript makes clear that the district court was firm in its
ruling and indicated that defense counsel needed to move on. In
fact, the district court explicitly told defense counsel, "[n]o,
you can't impeach by omission. How many times do I have [to] tell
you?" Under these circumstances, we think counsel reasonably could
have assumed that any further pursuit of the impeachment would
only signal disrespect for the court's decision. Because the
district court's other evidentiary errors already warrant a new
trial, we need not say more on the issue, except that in any
- 39 -
proceedings that follow this appeal, Villa should be permitted to
attempt impeachment along these lines.
IV. CONCLUSION
For the reasons discussed, we reverse the entry of final
judgment, vacate Villa's conviction, and order a new trial.15
15Because we conclude that Villa is entitled to a new trial,
we decline to address the procedural and substantive
reasonableness challenges to his sentence that he raises in his
opening brief, his argument that the district court erred by
limiting his cross-examination of Herrera regarding Herrera's
alleged bail violation and revocation, and his unpreserved Brady
challenge that he raised for the first time in a separate pro se
filing in this court. See United States v. Sanabria, 645 F.3d
505, 511 n.7 (1st Cir. 2011); United States v. Bristol-Martir,570 F.3d 29, 45
(1st Cir. 2009).
- 40 -
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