Source: s3://data.kl3m.ai/documents/govinfo/USCOURTS/USCOURTS-ca1-19-01485/USCOURTS-ca1-19-01485-0/pdf.json

Nature of Suit Code: 510
Nature of Suit: Prisoner Petitions - Vacate Sentence
Cause of Action: 

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United States Court of Appeals

For the First Circuit

No. 19-1485

ELVIN TORRES-ESTRADA,

Petitioner, Appellant,

v.

UNITED STATES OF AMERICA,

Respondent, Appellee.

APPEAL FROM THE UNITED STATES DISTRICT COURT

FOR THE DISTRICT OF PUERTO RICO

[Hon. Juan M. Pérez-Giménez, U.S. District Judge]

Before

Lipez, Thompson, and Kayatta, Circuit Judges.

Ezekiel E. Cortez for petitioner-appellant.

Julia M. Meconiates, 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 respondent-appellee.

December 6, 2024

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LIPEZ, Circuit Judge. In this collateral criminal 

appeal, we consider an ineffective assistance of counsel claim 

brought by a defendant who relied on the plea-bargaining advice of 

one of his attorneys despite warnings from his other attorneys

against accepting that advice. Appellant Elvin Torres-Estrada 

maintains that the bad advice -- along with that same attorney's 

obstruction of plea negotiations -- entitles him to resentencing 

under the principles of Missouri v. Frye, 566 U.S. 134 (2012), and 

Lafler v. Cooper, 566 U.S. 156 (2012).

More specifically, Torres-Estrada claims that, but for 

the ineffective assistance of his local counsel, he would have had 

a more favorable plea agreement and sentencing outcome: a likely 

term of 188 months' imprisonment instead of 288 months. He 

therefore argues that he is entitled to resentencing according to 

the terms originally proposed by the government. We disagree, 

concluding that his local attorney's representation was not 

constitutionally deficient and that Torres-Estrada's own decisionmaking drove the outcome of his plea-bargaining process. We

therefore affirm the district court's denial of sentencing relief.

I.

A. Overview

In April 2010, Torres-Estrada and sixty-four other 

individuals were charged in a superseding indictment with, inter 

alia, conspiring to distribute large amounts of controlled 

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substances near a public housing project from roughly 1995 to

2009.1 As described in detail below, plea negotiations initiated 

by Torres-Estrada's attorneys stretched into the fall of 2010. 

Then, in February 2011 -- with no plea bargain relating to the 

earlier indictment yet in place -- Torres-Estrada and three others 

were charged in a separate, single-count indictment with 

conspiring to import controlled substances into the United States.2 

On the eve of trial on the initial charges, in March 2011, TorresEstrada signed a consolidated plea agreement in which he agreed to

plead guilty to one count of each indictment. The agreement 

specified that Torres-Estrada could request a sentence of 264 

months (twenty-two years), while the government was permitted to 

argue for a 288-month (twenty-four-year) term of imprisonment. As 

1 The original indictment was filed in September 2009, and 

Torres-Estrada remained a fugitive until June 2010. See United 

States v. Torres-Estrada, 817 F.3d 376, 377 (1st Cir. 2016). 

Torres-Estrada was charged in seven of the superseding

indictment's eleven counts. Count One charged the conspiracy to 

possess with intent to distribute controlled substances near a 

public housing project. Counts Three through Six charged him with 

possession with intent to distribute various drugs: heroin (Count 

Three), crack cocaine (Count Four), cocaine (Count Five), and 

marijuana (Count Six). He was charged in Counts Seven and Eleven 

with conspiring to commit money laundering.

2 A superseding indictment filed in the second case in 

September 2013 charged twenty-seven additional defendants with 

conspiring to import, and to possess with the intent to distribute,

controlled substances. The superseding indictment also charged 

those individuals with conspiracy to commit money laundering and 

international money laundering.

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noted above, the district court imposed the higher of those two 

possibilities.3

Following an unsuccessful direct appeal, Torres-Estrada 

filed a motion to vacate, set aside, or correct his sentence under 

28 U.S.C. § 2255, raising the ineffective assistance of counsel 

claim that is at issue in this appeal,4 among other rationales for 

vacating his convictions and sentence. The district court rejected 

all grounds for relief. See Torres-Estrada v. United States, Civ. 

No. 17-1373, 2019 WL 1878294, at *8 (D.P.R. Apr. 26, 2019). We 

granted a certificate of appealability solely on the question of 

whether Torres-Estrada received ineffective assistance from his 

local counsel "in relation to plea-bargain negotiations with the 

United States." We therefore set forth below only the facts 

relevant to that issue,5 drawing primarily from the affirmations

filed by Torres-Estrada and one of his attorneys in the district 

3 The court sentenced Torres-Estrada to the 288-month term on 

the first indictment and imposed a concurrent 120-month term for 

the importation conspiracy. See Torres-Estrada, 817 F.3d at 378.

4 Although Torres-Estrada pressed his ineffective assistance 

of counsel claim in his direct appeal, we did not address the issue 

there. See 817 F.3d at 378-79.

5 Torres-Estrada includes in his brief an argument based on 

attorney conflict-of-interest. That issue is not only outside the 

scope of this appeal but also was disposed of during 

Torres-Estrada's direct appeal. See 817 F.3d at 378 n.2. We 

therefore do not address it.

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court.6 The facts are largely undisputed; the debate concerns 

their legal significance.

B. The First Indictment and Early Plea-Bargaining Process

Following Torres-Estrada's arrest in June 2010 on the 

charges alleged in the first indictment, New York attorneys Raymond 

Granger and Edward Sapone appeared pro hac vice on his behalf at 

a bail hearing, along with a local counsel who later withdrew from 

the case. Shortly thereafter, Ramón Garcia Garcia ("Garcia"), 

also a local Puerto Rico attorney, filed a notice of appearance to 

join the defense team. According to Torres-Estrada, Garcia, who

had been his attorney for an unrelated Commonwealth criminal 

matter, had asked to join the defense in the federal case as local 

counsel.

Early in their representation, Granger and Sapone 

concluded that Torres-Estrada might benefit from a joint plea deal 

with one of his co-defendants, Samuel Negron-Hernandez. With their 

client's agreement, the two attorneys began coordinating with 

Negron-Hernandez's attorneys, Rafael Castro-Lang and Steven 

Potolsky. Through that collaboration, and from meetings with the 

lead prosecutor, Granger and Sapone learned that the government 

6 An "affirmation" given in the context of legal proceedings 

is defined as "[a] solemn or formal declaration or asseveration 

. . . that the witness will tell the truth, . . . this being 

substituted for an oath in certain cases." The L. Dictionary, 

"Affirm Definition & Legal Meaning," 

https://thelawdictionary.org/affirm [https://perma.cc/F67U-PTJ7].

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had refused a proposed eleven-year term of imprisonment for 

Negron-Hernandez and would be seeking a sentencing recommendation 

for Torres-Estrada roughly two years longer than 

Negron-Hernandez's based on the government's view of their 

relative culpability. Garcia did not attend most of these

meetings, consistent with his limited role as local counsel.

On September 20, 2010, via email, the government offered 

Torres-Estrada a plea deal that allowed him to request a 188-month 

sentence (fifteen years/eight months), while the government would 

argue for a sentence up to 210 months (seventeen years/six months). 

In his affirmation, Granger stated that the prosecutor, Assistant 

United States Attorney ("AUSA") Timothy Henwood, made two 

representations about the proposed plea deal that were not included

in the email: (1) the government would not strongly argue for the 

higher sentence, with the expectation that the district court would 

accept the defense recommendation based on its "track record of 

honoring plea agreements," and (2) the government would not 

prosecute Torres-Estrada on additional charges. At about the same 

time, Negron-Hernandez was offered a deal allowing him to argue 

for a sentence of 168 months (fourteen years).

On September 22, two days after receiving the 

government's plea offer, Granger and Sapone met with one of 

Negron-Hernandez's attorneys, Castro-Lang, to discuss how to 

respond. The attorneys concluded that counteroffers would be 

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appropriate since Henwood had not said that the government's offers 

were final. They settled on a joint counteroffer of twelve years 

(144 months) for Negron-Hernandez and fourteen years (168 months) 

for Torres-Estrada -- consistent with the understanding that the 

government wanted a two-year differential between the two 

defendants and the government's rejection of Negron-Hernandez's

earlier proposal for an eleven-year sentence. The attorneys 

further "reasoned that, even though the government might reject 

[those counteroffers, they] would be considered reasonable and 

might induce the government at least to lower the offers it had 

just made."

Garcia also attended this meeting, having been invited 

"as a matter of courtesy." Granger recounted that, at some 

point during the strategy discussion, "Mr. Garcia suddenly 

interjected that he was going to recommend to Mr. Torres-Estrada 

that the [counteroffer] for him should be 13 years (156 months),"

rather than fourteen years (168 months). When Castro-Lang pointed 

out that such a counteroffer was inconsistent with the government's 

demand for a two-year spread between the two defendants, Garcia 

responded that he "did not care about" Negron-Hernandez. Granger 

pushed back, noting that the government's offers were premised on 

both defendants pleading guilty and that Torres-Estrada had 

benefited from the sharing of information between the two sets of 

attorneys. When the meeting ended, the four attorneys, as well as 

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Potolsky, headed to MDC Guaynabo to speak jointly with their 

clients.

At that client meeting, the lead attorneys discussed the 

government's plea offers and explained "why [they] believed them 

to be excellent offers that should be given serious consideration." 

The attorneys also explained why they nevertheless believed

counteroffers were appropriate, the basis for the specific 

counteroffers they were proposing, and why they felt it was 

important to reach a plea deal soon. Among other factors, they 

cited the need for a two-year differential in the proposed 

sentences; AUSA Henwood's insistence on guilty pleas before the 

first trial in the case, which was then scheduled for late October

2010; and the risk that "delaying too long could result not just 

in the offer being withdrawn by the government but also in new 

charges being lodged against them based on new information." In 

emphasizing the need to act promptly, the attorneys also pointed 

out that "another defendant viewed [as] less culpable by the 

government might reach a plea bargain with the government in the 

meantime that potentially could raise the minimum sentence[s] that 

the government would insist upon for" Torres-Estrada and 

Negron-Hernandez.

According to Granger, by the end of the meeting, all 

five attorneys -- including Garcia -- agreed that the counteroffers 

should be fourteen years' (168 months') imprisonment for 

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Torres-Estrada and twelve years (144 months) for Negron-Hernandez. 

Granger stated that the two defendants also were advised that the 

attorneys "considered these to be the lowest [counteroffers] the 

government would consider credible in light of the prior plea 

negotiations and of offers made to other defendants in the case." 

Torres-Estrada and Negron-Hernandez endorsed the proposed 

counteroffer strategy. Garcia did not bring up at this meeting 

the thirteen-year counteroffer he had earlier announced that he 

would recommend to Torres-Estrada.

However, Garcia met separately with Torres-Estrada 

several times, including after the September 22, 2010 meeting, and 

gave him advice at odds with the lead attorneys' positive 

assessment of the government's offer, explaining that "he knew 

better" than the New York-based lawyers about the plea-bargaining 

possibilities because "his entire legal career had been spent in 

Puerto Rico." According to Torres-Estrada in his affirmation, 

Garcia told him that drug suppliers in Puerto Rico typically 

receive sentences between eight and twelve years in length, and 

Garcia expressed confidence that "he could obtain a plea agreement 

in that range" for Torres-Estrada. At one point, Garcia advised

Torres-Estrada that he should not agree to a counteroffer of more 

than thirteen years (156 months) "because he [Garcia] did not 

believe the government had enough evidence to justify a sentence 

longer than that." Garcia also told Torres-Estrada that any 

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pre-trial plea offer from the government would remain available 

after the trial of the first group of defendants -- which at that 

time did not include Torres-Estrada -- and Garcia also suggested 

that he might be able to negotiate a better deal for Torres-Estrada 

after that initial trial. 

When Torres-Estrada told Granger and Sapone about 

Garcia's assertions, they responded that "Mr. Garcia was simply 

wrong and was giving him very bad advice." They explained, among 

other disagreements with Garcia, that plea deals in previous drugconspiracy cases in Puerto Rico "did not provide an accurate 

measure of what constituted a realistic plea bargain" for him 

because his case "involve[d] volumes of narcotics significantly 

higher than those in prior cases in Puerto Rico." 

Meanwhile, after the September 22 attorney-client 

meeting at MDC Guaynabo, Granger arranged for the four lead 

attorneys to meet with AUSA Henwood on September 28.

C. The Plea-Bargaining Events of September 27 and 28, 2010

On September 27, the day before the scheduled meeting 

with Henwood, Granger received the following email from Garcia:

Good morning Ray:

Yesterday I met with Elvin [Torres-Estrada] 

and he informed me that the [counteroffer] has

to be 13 years, he will not authorize a 

[counteroffer] of 14 years.

Have a nice day

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Ramon 

As set forth in his affirmation, Granger responded to Garcia at 

length. Among other criticisms, he chastised Garcia for discussing 

"pivotal issues" with Torres-Estrada without consulting the lead 

attorneys, asserted that Garcia was undermining the other 

attorneys "to the [] client's detriment," and had "raised

[Torres-Estrada]'s expectations to unrealistic levels." Granger 

reminded Garcia that the government had rejected 

Negron-Hernandez's eleven-year proposed sentence and "ha[d]

insisted on approximately a two-year spread between" the two 

defendants. Granger also pointed out that Garcia had agreed with 

the other lawyers' strategy during the session at MDC Guaynabo, 

and he asserted that Garcia should have advised Torres-Estrada not 

to make "such an important decision" -- i.e., changing the proposed 

counteroffer -- "without first conferring with all the attorneys 

involved and with [Negron-Hernandez]."

The next morning, before meeting with AUSA Henwood, 

Granger and Sapone went to MDC Guaynabo to discuss Garcia's email 

with Torres-Estrada. They told him that it was "inappropriate" 

for Garcia to advise him to change the agreed-upon counteroffer 

"not only because it was beyond his role as local counsel" but 

also because "no changes in strategy should be made without first 

consulting [Negron-Hernandez's] attorneys." They pointed out that

it was "extraordinarily irresponsible for Mr. Garcia to upset the 

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joint-defense planning at the last minute." The attorneys also 

told Torres-Estrada that they "had observed a deterioration in his

emotional and mental state" in recent weeks and that, in their 

view, "Mr. Garcia was capitalizing on his weakened condition and 

manipulating him."7 They again explained the basis for the twelveand fourteen-year counteroffers and told Torres-Estrada that a 

thirteen-year counteroffer "would be a fundamental, and likely 

disastrous, mistake." They reiterated that "time was of the 

essence" and that Garcia's suggestion that the government's same 

plea offer would remain available after the first trial "made no 

sense and, in any event, was contrary to AUSA Henwood's explicit 

warning" that the offer would not extend beyond the first trial.

After this discussion, Torres-Estrada authorized the 

lead attorneys to make a counteroffer of thirteen years/eight 

months (164 months), with Granger recalling that he "appeared

confused and to struggle with his decision." Although Granger 

recommended against including Garcia in the meeting with Henwood 

later that day, Torres-Estrada said he wanted all three of his 

7 In his affirmation, Torres-Estrada reported that his 

attorneys had expressed this concern, but he did not state that he

had in fact felt manipulated by Garcia. Rather, he said that he 

was "confused and nervous" when Garcia told him that he should not 

authorize a counteroffer of more than thirteen years' imprisonment 

shortly after the lead attorneys had secured his agreement to the

fourteen-year counteroffer. He reported that he was "unsure what 

to do" and ultimately deferred to Garcia, "notwithstanding [his] 

doubts," after Garcia "persisted."

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lawyers present. Granger therefore notified Garcia to meet the 

others at the U.S. Attorney's office in San Juan. While the 

attorneys were gathered in the reception area, Granger and Sapone 

told Garcia that Torres-Estrada had agreed to a thirteenyear/eight-month counteroffer during their meeting with him 

earlier in the day. Shortly thereafter, the attorneys entered the 

conference room for the meeting with Henwood.

In the meeting, Castro-Lang first argued for a lower 

plea offer for Negron-Hernandez and proposed the twelve-year

(144-month) term. Henwood responded that the offer was 

"reasonable." Granger then spoke on behalf of Torres-Estrada, 

explaining that Sapone would add comments and then present their 

counteroffer. As Granger was turning to Sapone for his remarks, 

however, Garcia interrupted and told Henwood that Torres-Estrada's 

counteroffer was thirteen years (156 months). When Henwood 

immediately rejected that offer, Garcia asked if he would consider 

thirteen years/six months (162 months). Henwood said he would 

think about it, and Garcia then left. The meeting ended a short 

time later. Granger's affirmation does not report any comments by 

Henwood after Garcia's departure.

Following the meeting, Granger returned to MDC Guaynabo 

and told Torres-Estrada "the meeting had not gone well." In 

describing what happened, Granger said that, because Henwood had 

characterized the twelve-year (144 months) offer for 

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Negron-Hernandez as reasonable, he and Sapone believed the 

prosecutor also would have considered reasonable a fourteen-year

(168-month) counteroffer for Torres-Estrada -- "and possibly even 

one of 13 years and 8 months" (164 months) -- and that such an 

offer "would not have spoiled the negotiating atmosphere." Granger 

again told Torres-Estrada that he "felt Mr. Garcia was manipulating 

him at a time when his emotional and mental state had been 

deteriorating." Granger said he planned to meet with Garcia the

next day, and Torres-Estrada agreed that he should.

D. The Plea-Bargaining Events Following the September 28 Meeting

As he left the meeting with AUSA Henwood, Garcia 

indicated that he would be available to meet with Granger the next 

day. Nonetheless, Garcia refused to do so. Granger also learned 

that morning -- i.e., on September 29, 2010 -- that the government 

would not lower the plea offers. After conferring with Sapone and 

Negron-Hernandez's attorneys, Granger sent an email to Henwood

explaining that Garcia's interjected thirteen-year counteroffer 

was unauthorized by their client and that he and Sapone were 

"furious" when Garcia intervened in the discussion. Granger 

reported that even Garcia's follow-up counteroffer of thirteen 

years/six months (162 months) was lower than Torres-Estrada had 

authorized (a counteroffer of 164 months). The email, sent on 

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September 30, included the following assessment of the meeting and 

request to continue negotiations:

My sense, particularly after your having 

described [Castro-Lang]'s [counteroffer] as 

"reasonable," is that the counters made by 

Garcia were viewed as so unreasonable that 

they spoiled the negotiating atmosphere, 

resulting in your supervisors becoming so 

annoyed that they refused to authorize any 

movement by your side even if they otherwise 

might have considered it. . . .

The bottom line is that Ed [Sapone], Rafael

[Castro-Lang], Steve [Potolsky], and I believe 

a deal is still possible and would appreciate 

a chance to discuss that possibility. Do you 

have a few minutes later today or tomorrow to 

talk?

In his affirmation, Granger reported that he "continued 

to communicate with AUSA Henwood in early October 2010 in an effort 

to get the government to reconsider its position." Meanwhile, 

Granger learned that Garcia also was attempting to meet with the 

government. On October 8, Granger sent Garcia a letter telling 

him to stop such efforts. Granger told Garcia that Torres-Estrada 

had authorized Sapone and him to continue the negotiations, and 

Granger informed Garcia that Henwood had agreed to "discuss with 

his supervisor whether to reconsider the government's present 

position." The letter to Garcia concluded with the following 

paragraph:

As Mr. Torres-Estrada knows, I have 

explained to AUSA Henwood that you spoke out 

of turn and inconsistent with Mr. 

Torres-Estrada's instructions at the meeting 

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held on September 28. It is on that basis 

that AUSA Henwood agreed to revisit the issue 

of whether the government would be willing to 

lower its offers to both Mr. Torres-Estrada 

and Samuel Negron-Hernandez. . . . After I 

had spoken with AUSA Henwood earlier this 

week, Mr. Torres-Estrada advised me that he 

wanted to hear the government's response, 

which AUSA Henwood believes he will be in a 

position to convey later today. Accordingly, 

any further efforts by you to negotiate with 

the government would be contrary to our 

instructions, but would also, in any event, 

make little sense.

Roughly a week later, on October 14, AUSA Henwood, 

apparently having consulted with his supervisor, confirmed to

Granger that the original offer to Torres-Estrada -- fifteen 

years/eight months (188 months) -- would not be reduced.8

Torres-Estrada was informed of the government's position, stating

in his affirmation that he learned "[i]n early October 2010 

. . . that the government had refused to lower its original plea 

offer of 188 months' (15 years, eight months') imprisonment and 

that it was the government's final offer." According to TorresEstrada, Garcia nonetheless continued to advise him "in one or 

more meetings at MDC Guaynabo not to believe that that was the 

government's final offer, and that he [Garcia] would be able to 

8 We note that, in describing the various offers under 

discussion, we refer generally to the sentencing recommendation 

that would be made by Torres-Estrada rather than the higher 

recommendation that the government would be authorized to make. 

As recounted above, both parties anticipated that the district 

court would adopt each defendant's recommendation. See supra 

Section I.B.

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obtain a better deal than that from the government." Garcia also 

told Torres-Estrada that, if he discharged Granger and Sapone, 

Garcia could invoke the change of counsel in requesting that 

Torres-Estrada be excluded from the first group of defendants 

scheduled for trial later in October.

On October 15, 2010, Granger and Sapone filed notices to 

withdraw from representing Torres-Estrada, which Granger said they 

did at Torres-Estrada's direction. According to Torres-Estrada, 

Garcia thereafter "repeatedly told [him] that the government was 

still considering his [counteroffer] of 162 months' (13 years, 6 

months') imprisonment." In a sworn statement, Garcia reported 

that he had attempted to meet with AUSA Henwood "[s]ince December 

2010," but received no response before the government resumed 

negotiations after the filing of the second indictment in February 

2011.9 According to the government, the plea negotiations were 

suspended when it developed evidence that, in addition to the 

previously charged conspiracy, Torres-Estrada "had also been a 

principal member of a narcotics importation organization that 

9 Garcia's statement was included as an attachment to a 

supplemental motion in which Torres-Estrada asked to file a reply 

to the government's response to his § 2255 motion. The district 

court denied the motion because the deadline for filing a reply 

had passed. However, Garcia's statement is largely consistent 

with the affirmations of Granger and Torres-Estrada, and we

therefore choose to refer to the statement in recounting the

background of the case. We note, in addition, that Torres-Estrada 

appears to correctly assert that the district court granted the 

government more leeway with deadlines than it allowed him. 

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brought large shipments of cocaine from the Dominican Republic to 

Puerto Rico."

E. The Second Indictment, Plea Process, and Lafler-Frye Motion

Torres-Estrada's circumstances in early 2011 were 

complex. In addition to the new charges in the importation

indictment, Torres-Estrada was facing trial in March on the 

original charges.10 According to Torres-Estrada, after the trial 

was set for March 21, Garcia told him he could get it delayed --

"thereby gaining more time to negotiate a plea bargain" -- because 

Garcia had another case going to trial in March that would take 

priority.11 On March 18, 2011, Garcia met with Torres-Estrada at 

MDC Guaynabo. Although Torres-Estrada and Garcia recounted some 

details of this conversation differently, the basic thrust of 

Garcia's message was that the resumed plea negotiations were 

focused on a deal that would provide for a proposed sentence of 

264 months (twenty-two years) in exchange for a guilty plea to 

both indictments. According to Torres-Estrada, Garcia recommended 

10 Torres-Estrada was now among the first group of defendants 

to be tried, with the trial rescheduled from fall 2010 to March

2011.

11 Garcia did file a motion to sever Torres-Estrada's case 

from those of the other defendants scheduled for trial in March

based on the timing of the trial in his other case and on the need 

to obtain and review discovery related to the new indictment. 

Garcia also stated in the motion that he "had been negotiating

with the government to try to reach a plea agreement that would 

have disposed of the case." The motion, which was filed on 

February 23, was denied on March 4.

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that he agree to such a deal. That same day, Garcia filed a motion 

for a change of plea for Torres-Estrada, and the district court 

scheduled a change-of-plea hearing for March 21 -- the day jury 

selection was scheduled to start.

On the morning of March 21, Garcia presented 

Torres-Estrada with a plea agreement in writing for the first time. 

It contained the sentencing proposal that the attorney had 

partially described a few days earlier, allowing Torres-Estrada to 

request a sentence of 264 months (twenty-two years) but stating 

that the government reserved the right to argue for 288 months

(twenty-four years). The agreement was in English, and because he 

has "only limited ability to read English," Torres-Estrada asked 

Garcia to help him review the document. Garcia then explained the 

provisions as they "browsed it together." In his affirmation, 

Torres-Estrada said he did not fully understand the provisions and 

was "frightened and confused," but he felt compelled to sign the 

agreement because "Mr. Garcia clearly was unprepared to begin the 

trial" that otherwise would have started that day.12

Within weeks after signing the plea agreement, 

Torres-Estrada "discharged" Garcia and hired new counsel -- part 

12 Negron-Hernandez also signed a consolidated plea agreement 

on the same day that resolved both cases against him. The 

agreement allowed Negron-Hernandez to request a sentence of 210 

months (seventeen and one-half years) and the government to argue 

for 240 months' (twenty years') imprisonment.

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of a flurry of changes in defense attorneys during the next couple 

of years that included a brief reappearance by Garcia and, most 

notably, the rehiring of Granger and Sapone in August 2011. In 

June 2012, in advance of Torres-Estrada's then-scheduled 

sentencing later that month, Granger filed a motion asserting that 

Garcia had rendered ineffective assistance of counsel and seeking 

an order that Torres-Estrada be given the benefit of the fifteenyear/eight-month (188-month) plea bargain the government had 

offered in September 2010.13 This so-called Lafler-Frye motion, 

named for the two leading Supreme Court cases detailing the 

obligations of attorneys in plea negotiations, included a request

for an evidentiary hearing. See Lafler v. Cooper, 566 U.S. 156 

(2012); Missouri v. Frye, 566 U.S. 134 (2012). The district court 

denied the motion in September 2012 in a docket order, without 

explanation.

Roughly two-and-a-half years later, after the sentencing 

hearing was rescheduled multiple times for various reasons,14

Torres-Estrada was sentenced in February 2015 to the twenty-fouryear (288-month) term of imprisonment recommended by the 

13 The affirmations of Granger and Torres-Estrada on which we 

have relied to describe the plea-bargaining process were submitted 

in connection with this motion.

14 Some of the delay is attributable to the changes in defense 

counsel, including the second withdrawal of Granger and Sapone in 

January 2013.

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government pursuant to the plea agreement. As described above, 

after we affirmed his conviction and sentence on direct appeal, 

Torres-Estrada unsuccessfully sought relief in the district court 

under § 2255 on the ground, inter alia, that Garcia's ineffective 

assistance deprived him of the more favorable fifteen-year/eightmonth (188-month) plea deal originally offered by the government. 

In rejecting that claim, the district court concluded that Garcia's 

strategy was "sound," that the conduct challenged by 

Torres-Estrada as ineffective assistance of counsel "is nothing 

more than infighting between the attorneys caused or allowed by 

Torres-Estrada himself," and that Torres-Estrada had failed to 

show prejudice. Torres-Estrada, 2019 WL 1878294, at *6.15

As noted, we granted Torres-Estrada's request for a 

certificate of appealability on his Sixth Amendment claim, 

concluding that Torres-Estrada had raised an issue of deficient 

representation by Garcia "in relation to plea-bargain negotiations 

with the United States" sufficiently debatable to warrant our 

review. Torres-Estrada v. United States, No. 19-1485 (1st Cir. 

15 With respect to prejudice, the district court stated that 

"there is nothing in the record that shows that [Torres-Estrada] 

would have accepted [the government's original offer]

. . . because even 'lead counsel' was advocating for a 14-year 

counter-offer" and Torres-Estrada "decided to authorize one for 13 

years and 8 months." Torres-Estrada, 2019 WL 1878294, at *6. The 

court further observed that Torres-Estrada "has failed to show 

that the trial court would have accepted the 188-month sentencing 

recommendation." Id. at *7.

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Feb. 23, 2022), ECF No. 15; see also, e.g., Feliciano-Rodríguez v. 

United States, 986 F.3d 30, 36 (1st Cir. 2021) (explaining that a 

petitioner seeking a certificate of appealability "must make 'a 

substantial showing of the denial of a constitutional right'" --

i.e., "'that the issues are debatable among jurists of reason'" 

(first quoting 28 U.S.C. § 2253(c)(2), then quoting Barefoot v.

Estelle, 463 U.S. 880, 893 n.4 (1983))). We now turn to our 

discussion of that claim.16

II.

In Frye, the Supreme Court held for the first time that 

"the constitutional right to counsel extends to the negotiation 

and consideration of plea offers that lapse or are rejected," and 

it reiterated the longstanding principle that "[t]he right to 

counsel is the right to effective assistance of counsel." 566 

U.S. at 138.17 In both Frye and Lafler, decided the same day, the 

16 Although Torres-Estrada asserts in his brief that Garcia

was unprepared for trial in March 2011, and that he therefore felt

pressure to sign the consolidated plea agreement on the morning 

the trial was scheduled to begin, this aspect of Garcia's alleged 

poor performance is undeveloped and outside the narrow scope of 

our review (limited to Garcia's plea-negotiation conduct). We 

therefore do not further address this assertion. 

17 As the Court noted in Frye, prior cases had established 

that the Sixth Amendment applied to defense counsel's obligations 

"in advising a client with respect to a plea offer that leads to 

a guilty plea." 566 U.S. at 141 (discussing Hill v. Lockhart, 474 

U.S. 52 (1985), and Padilla v. Kentucky, 559 U.S. 356 (2010)). 

The claims in those cases had focused on counsel's "incorrect 

advice" that "le[d] to acceptance of a plea offer." Id. at 141-

42. Frye and its companion case, Lafler, differed because "[t]he 

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performance of defense counsel in the plea-bargaining process was 

determined to be constitutionally deficient. See infra. 

Torres-Estrada argues that his Sixth Amendment claim is equivalent

to those considered in Frye and Lafler and that, based on the 

precedent they established, he is entitled to resentencing

consistent with the government's original plea offer. We review

the law governing Torres-Estrada's Sixth Amendment claim, and the 

Supreme Court's application of that law in Frye and Lafler, before

turning to Torres-Estrada's contention that he has established a 

constitutional violation entitling him to relief.

A. The Ineffective-Assistance-of-Counsel Inquiry

When evaluating a Sixth Amendment claim of ineffective 

assistance of counsel brought under 28 U.S.C. § 2255, we conduct

a two-pronged inquiry, asking whether (1) counsel provided

objectively deficient representation (the performance prong), and, 

if so, (2) is there "a reasonable probability that, but for 

counsel's unprofessional errors, the result of the proceeding 

would have been different" (the prejudice prong)? Strickland v. 

Washington, 466 U.S. 668, 688, 694 (1984); see also Casey v. United 

States, 100 F.4th 34, 42 (1st Cir. 2024). "The petitioner bears 

a heavy burden on each prong." Casey, 100 F.4th at 42.

challenge[s] [were] not to the advice pertaining to the plea that 

was accepted but rather to the course of legal representation that 

preceded it with respect to other potential pleas and plea offers." 

Id.

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Attorney performance will be found deficient "[o]nly

when counsel's strategy was 'so patently unreasonable that no 

competent attorney would have made it.'" Watson v. United States, 

37 F.4th 22, 28 (1st Cir. 2022) (quoting Tevlin v. Spencer, 621 

F.3d 59, 66 (1st Cir. 2010)). For claims asserting deficient 

performance in plea negotiations, the prejudice prong requires 

defendants to prove that "the outcome of the plea process would 

have been different with competent advice." Lafler, 566 U.S. at 

163. That is, "defendants must demonstrate a reasonable 

probability they would have accepted" a lower plea offer and that 

"the plea would have been entered without the prosecution canceling 

[the offer] or the trial court refusing to accept it." Frye, 566 

U.S. at 147; see also Rivera-Rivera v. United States, 844 F.3d 

367, 372-73 (1st Cir. 2016).

In reviewing the district court's rejection of 

Torres-Estrada's claim of ineffective assistance of counsel, we 

assess any factual findings for clear error and the court's legal 

conclusions de novo. See Casey, 100 F.4th at 44. Both prongs of 

the ineffective-assistance "inquiry are mixed questions of law and 

fact," United States v. Valerio, 676 F.3d 237, 246 (1st Cir. 2012)

(quoting Strickland, 466 U.S. at 698), and the applicable standard 

of review depends on whether "a particular question is 

fact-dominated or law-dominated," id. (quoting Dugas v. Coplan, 

506 F.3d 1, 8 (1st Cir. 2007)). The district court did not hold 

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an evidentiary hearing and thus made no explicit findings of fact. 

We see the inquiry here as law-dominated and, accordingly, review 

the district court's decision de novo.

B. Frye and Lafler

In Frye and Lafler, the Supreme Court addressed two 

different scenarios in which defendants claimed that their 

attorneys' ineffective assistance caused their failure to take 

advantage of a plea offer, with the result that "further 

proceedings led to a less favorable outcome." Lafler, 566 U.S. at 

160; see also Frye, 566 U.S. at 138. As we shall describe, both

scenarios inform our assessment of the case now before us. 

In Frye, the defendant's attorney never told his client

that the prosecutor had offered two possible plea bargains and had 

given an expiration date for making a choice. See 566 U.S. at 

138-39. The offers lapsed, and Frye subsequently pled guilty 

without a plea agreement, subjecting him "to a maximum sentence of 

four years instead of one year." Id. at 139-40 (internal quotation 

marks omitted). The Court (a five-justice majority) concluded

that Frye's attorney, by failing to "make a meaningful attempt to 

inform the defendant of a written plea offer before the offer 

expired," id. at 149, had provided representation that "fell below 

an objective standard of reasonableness," id. (quoting Strickland, 

466 U.S. at 688).

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The prejudice prong of the Strickland inquiry was less 

straightforward. By the time of the scheduled preliminary hearing 

and guilty plea, Frye had committed an additional offense. See

id. at 139, 151. The Supreme Court observed that the new arrest, 

among other considerations, gave "reason to doubt that the 

prosecution would have adhered to the agreement or that the trial 

court would have accepted it . . . unless they were required by 

state law to do so." Id. at 151. The Court therefore remanded 

the case to the state appeals court so it could address the 

state-law questions bearing on the prejudice question "in the first 

instance." Id.

In Lafler, the defendant was charged with five state-law 

crimes related to his shooting of a woman who survived his assault. 

Id. at 161. The prosecutor initially offered to dismiss some of 

the charges and to recommend a negotiated sentence covering the 

remaining charges. Id. Based on the incorrect understanding that 

the defendant "could not be convicted at trial,"18 defense counsel 

18 As the Supreme Court described the alleged circumstances, 

defense counsel had told Lafler he "could not be convicted for 

assault with intent to murder as a matter of law" because he had 

shot the victim below the waist. 566 U.S. at 174. That assurance 

rested on an objectively incorrect explanation of the law. See

id. at 161-63 (noting the Sixth Circuit's determination that 

counsel had informed Lafler of "an incorrect legal rule" (quoting 

Cooper v. Lafler, 376 Fed. App'x 563, 570 (2010))). The case came 

to the Supreme Court with all parties agreeing that counsel's 

performance "was deficient when he advised [Lafler] to reject the 

plea offer on the grounds he could not be convicted at trial." 

Id. at 163.

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advised his client to reject that plea offer and the defendant 

also rejected another plea deal offered on the first day of trial. 

Id. at 163. The defendant thereafter had "a full and fair trial," 

in which the jury found him guilty on all counts. Id. at 160-61. 

He was sentenced to a "mandatory minimum sentence of 185 to 360 

months' imprisonment," id. at 161, which the Supreme Court observed 

was a minimum more than three times longer than the minimum in the 

original plea offer (fifty-one months), id. at 174.

The Court found that Lafler had satisfied Strickland's 

two-part test for ineffective assistance of counsel claims: The 

parties had conceded that defense counsel's performance was 

deficient, and the defendant "ha[d] shown that but for counsel's 

deficient performance there is a reasonable probability he and the 

trial court would have accepted the guilty plea." Id. The Supreme 

Court remanded the case for further proceedings so the trial court 

could determine an appropriate remedy. See id. at 174-75.19

19 Lafler's case was in federal court pursuant to a petition 

for habeas relief under 28 U.S.C. § 2254. The district court had 

"ordered specific performance of the original plea agreement," but 

the Supreme Court stated that "[t]he correct remedy in these 

circumstances . . . is to order the State [of Michigan] to reoffer 

the plea agreement." 566 U.S. at 174. The Court explained that, 

if the defendant accepted the renewed offer, the state trial court 

would have discretion to determine how to proceed. Id. Among the 

choices noted by the Court were vacating the convictions, with

resentencing pursuant to the plea agreement, and "leav[ing] the 

convictions and sentence from trial undisturbed." Id. (citing a 

state rule giving the court such discretion).

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In addition to the guidance provided by these two fact 

patterns, the justices in Frye made general observations about 

plea negotiations that are pertinent here. The Court acknowledged

the challenge of "defin[ing] the duty and responsibilities of 

defense counsel in the plea bargain process," 566 U.S. at 144, and 

noted the "nuanced" nature of "[t]he art of negotiation," id.

(quoting Premo v. Moore, 562 U.S. 115, 125 (2011)); see also Premo, 

562 U.S. at 124 ("Plea bargains are the result of complex 

negotiations suffused with uncertainty, and defense attorneys must 

make careful strategic choices in balancing opportunities and 

risks."). The Frye Court then continued:

Bargaining is, by its nature, defined to a 

substantial degree by personal style. The 

alternative courses and tactics in negotiation 

are so individual that it may be neither 

prudent nor practicable to try to elaborate or 

define detailed standards for the proper 

discharge of defense counsel's participation 

in the process.

566 U.S. at 145. The Court observed that, in any event, it had no 

need to formulate such standards for Frye's situation because it 

was clear that Frye was denied "the effective assistance the 

Constitution requires" when "counsel allowed the [plea] offer to 

expire without advising [him] or allowing him to consider it." 

Id.

With this background in mind, we turn to 

Torres-Estrada's claim that Garcia's representation was 

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constitutionally deficient and that he would have achieved a more 

favorable plea-bargaining outcome "with competent advice." 

Lafler, 566 U.S. at 163.

III.

We have no doubt that Garcia overstepped his intended 

role as local counsel during the plea-bargaining process.20 Most 

significantly, he interrupted the carefully planned negotiation 

session with AUSA Henwood on September 28, 2010, to make an 

unauthorized counteroffer, and he met with Torres-Estrada 

independently -- and secretly -- to persuade him to demand a lower 

proposed sentence than the one that had been agreed upon by the 

two defendants and all five defense attorneys (including Garcia). 

Garcia also attempted to meet independently with the government 

while Granger and Sapone remained the lead attorneys and, after 

they withdrew, he may have misrepresented (or at least overstated) 

the status of the plea negotiations when he told Torres-Estrada

that the government was still considering the specific

counteroffer of thirteen years/six months (162 months).

20 The district court noted that neither the federal nor Puerto 

Rico rules governing criminal procedure "make a distinction 

between lead and local counsel," and thus "all counsel appearing 

in a case are fully accountable to their client and the court 

regardless of the term used." Torres-Estrada, 2019 WL 1878294, at 

*4. Granger and Sapone, however, viewed Garcia's role as more 

limited than theirs as lead counsel, and Torres-Estrada agreed to 

that limitation.

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But acknowledging certain of Garcia's actions as

troubling does not inevitably mean that his actions denied 

Torres-Estrada the effective assistance of counsel. To determine 

whether Torres-Estrada has satisfied Strickland's requirements for 

establishing a Sixth Amendment violation, we think it useful to 

separately examine the two primary aspects of Garcia's

representation challenged by Torres-Estrada: first, his conduct 

leading up to, and during, the defense's presentation of a 

counteroffer on September 28, and, second, his advice to 

Torres-Estrada apart from that meeting. 

A. The September 28 Negotiation Session

Before assessing the details surrounding the September 

28 meeting, we note that the facts here are a far cry from those 

at issue in Frye, which involved "an uncommunicated, lapsed plea"

offer from the government. 566 U.S. at 148. Unlike the defendant 

in Frye, Torres-Estrada had knowledge of the government's original 

plea proposal, and he was also an active participant in his plea 

process. Lafler is a closer analog in that it involves adverse 

consequences from the defendant's reliance on his attorney's 

advice. Indeed, Garcia's conduct at the September 28 meeting was 

arguably even more problematic because he made a counteroffer more 

aggressive than his co-counsel reported the client had authorized.

Yet, the relevant considerations in evaluating Garcia's 

conduct materially differ from those in Lafler. Here, in Garcia's 

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last face-to-face meeting with Torres-Estrada, Torres-Estrada 

authorized the aggressive proposal of thirteen years. That 

authority was called into question only by the assertions of his 

co-counsel just before the meeting with AUSA Henwood began.

Moreover, a counteroffer of thirteen years does not preclude making 

a subsequent offer of thirteen years and eight months, and in that 

sense can be seen as an aggressive preparing of the ground for the 

less-aggressive final offer. Finally, added to this mix is the 

fact that unlike in Lafler, Garcia's strategy was not objectively 

wrong in its understanding of the law. See 566 U.S. at 162. In 

fact, after Garcia blindsided Granger and Sapone with his thirteenyear proposal on the eve of the scheduled plea-negotiation meeting, 

the lead attorneys and Torres-Estrada settled on a lower

counteroffer than initially contemplated for the defense team to 

propose to Henwood the following day. And when Garcia subsequently

undercut that compromise counteroffer by another two months at the 

meeting (requesting thirteen years/six months, after quickly 

adjusting upward from the immediately rebuffed thirteen years),

Henwood still responded by saying he would think about it.

The circumstances surrounding the meeting thus diminish 

the force of Torres-Estrada's claim that Garcia's disruptive 

actions were incompatible with an attempt by competent counsel to 

secure the best possible deal for his client. Given Henwood's 

stated willingness at the meeting to consider Garcia's rogue 

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thirteen-year/six-month (162-month) proposal, one could reasonably

say that Garcia's aggressive (though discourteous) tactics had 

advanced the plea negotiations and, accordingly, were "within the 

range of competence demanded of attorneys in criminal cases." 

Strickland, 466 U.S. at 687 (quoting McMann v. Richardson, 397 

U.S. 759, 771 (1970)); see also id. at 689 ("There are countless 

ways to provide effective assistance in any given case."). 

But even if we were to conclude that Garcia's disregard 

of his co-counsel's and client's agreed-upon and more conservative 

plan for the negotiation session amounted to deficient 

performance, Torres-Estrada could not demonstrate ineffective

assistance of counsel on that basis because he would still be 

unable to satisfy Strickland's prejudice prong. Despite Granger 

and Sapone's view that the meeting with Henwood had gone poorly 

because of Garcia's interference, the record makes plain that 

Garcia's conduct did not result in termination of the pleabargaining process. Rather, as Granger reported to Garcia, after 

Henwood was told that Garcia "spoke out of turn and inconsistent 

with Mr. Torres-Estrada's instructions," Henwood "on that basis 

. . . agreed to revisit" the possibility of lowering the offers to 

both defendants. And, as late as October 14 -- more than two weeks 

after Garcia's hijacking of the negotiation session -- the original 

offer of fifteen years/eight months (188 months) remained on the 

table. See supra. Indeed, Granger filed a motion on October 13 

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asking to extend the original deadline for the acceptance of a 

plea deal, originally set for that day, because the parties were 

still in active plea negotiations.

In sum, we need not view Garcia's disruptive performance 

in advance of, and during, the September 28 meeting as entirely

defensible to conclude that Torres-Estrada has failed to establish 

a violation of his Sixth Amendment right to the effective 

assistance of counsel based on Garcia's interactions with lead 

counsel and Henwood. Before the September 28 plea 

negotiations -- and beyond -- all of his attorneys were counseling

Torres-Estrada to push for a more lenient plea deal, and the 

government's original offer remained available well after that

meeting. Moreover, given Henwood's reaction at the meeting to 

Garcia's second counteroffer, and the continuing discussion of a 

possible lower sentencing proposal, the record fails to show that 

Garcia's meeting-related tactics affected "the outcome of the plea 

process," as required to satisfy Strickland's prejudice prong. 

Lafler, 566 U.S. at 163.

B. The Advice to Prolong the Plea Negotiations

Both contemporaneously with the events surrounding the

September 28 meeting and, in its aftermath, Garcia gave 

Torres-Estrada advice that Torres-Estrada now challenges as 

constitutionally deficient. Garcia told Torres-Estrada that he 

could, and should, wait to accept a plea deal until after the first 

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trial of his co-defendants. He posited that the outcome of the 

trial could lead the government to make a more favorable offer, 

and he assured Torres-Estrada that, as a local attorney, he knew 

better and could secure a lower sentence than his New York-based 

lead counsel. Immediately after Henwood reported that the 

government would stick to its original plea offer -- in mid-October 

2010 -- Garcia urged Torres-Estrada to discharge Granger and Sapone

because it would delay his trial and give Garcia time to negotiate 

a better deal. Garcia subsequently told Torres-Estrada that the 

rejected offer of thirteen years/six months (162 months) was still 

being considered by the government when that consideration may 

have been Garcia's hope but not necessarily the reality. 

As indicated above, Garcia's advice to Torres-Estrada is

distinguishable from the attorney's assurances in Lafler because 

it amounted to a subjective assessment about the possible outcome 

of the plea-negotiation process rather than the guarantee of a 

particular outcome, based upon an incorrect statement of law, that 

Lafler's attorney gave to him. See supra note 18. As the 

government points out, advising a defendant to delay accepting a 

plea is not a novel strategy, and, in certain circumstances, might 

even prove advantageous -- for example, if an intervening trial of 

co-defendants reveals weaknesses in the government's evidence. 

See, e.g., Premo, 562 U.S. at 125 (noting that the government's 

"case can begin to fall apart as stories change, witnesses become 

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unavailable, and new suspects are identified"). Of course, as it 

turned out, Garcia plainly overestimated the strength of 

Torres-Estrada's prospects. When the initial trial was 

rescheduled to March, Torres-Estrada was included in the first

group of defendants. At the same time, the government was moving 

toward the second indictment.

With the benefit of hindsight, Torres-Estrada argues 

that Garcia's strategy of delay was so risky -- "so patently 

unreasonable" -- that "no competent attorney would have [pursued] 

it." Watson, 37 F.4th at 28 (quoting Tevlin, 621 F.3d at 66). 

But Garcia's performance cannot be evaluated based on what 

transpired later. See, e.g., Miller v. United States, 77 F.4th 1, 

6 (1st Cir. 2023) (stating that, when "appraising counsel's 

performance, . . . we must make 'every effort . . . to eliminate 

the distorting effects of hindsight'" (second ellipsis in 

original) (quoting Strickland, 466 U.S. at 689)). As the Supreme 

Court noted, plea negotiations are by their nature "suffused with 

uncertainty," and, inevitably, the results of a defense attorney's 

"balancing [of] opportunities and risks" will not always be 

successful. Premo, 562 U.S. at 124. If the government had been 

unable to develop sufficient evidence to charge Torres-Estrada in 

the importation conspiracy, Garcia's effort to extend the plea 

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negotiations on the first indictment may have had a more favorable 

outcome.21

Indeed, if Garcia had been Torres-Estrada's only 

attorney and had advised the same aggressive strategy of delaying 

acceptance of the government's offer while pursuing a better deal, 

we could not say that Garcia's tactics -- i.e., his "personal 

style" of bargaining, Frye, 566 U.S. at 145 -- amounted to 

ineffective assistance of counsel, despite the strategy's ultimate 

lack of success. The counteroffers that the attorneys had planned 

to make at the September 28 meeting -- twelve years (144 months) 

for Negron-Hernandez and thirteen years/eight months (164 months) 

for Torres-Estrada -- featured the same twenty-month differential 

contained in the government's original plea offer (fourteen years 

and fifteen years/eight months). Garcia's attempt to slightly 

narrow that gap for Torres-Estrada, and his continuing effort to 

move the needle away from the government's original proposal, may 

21 The impact of the second indictment on the government's 

approach to a plea deal is reflected in Negron-Hernandez's efforts 

to reach an agreement. On November 30, 2010, his attorney filed 

a motion asking for another extension of the deadline for 

finalizing plea negotiations, explaining that "[t]he prosecutor 

apparently due to the heavy workload has been unable to inform 

defendant of the final terms of a plea offer which includes the 

forfeiture provisions." Then in February, roughly a week after 

the second indictment was issued, Henwood emailed 

Negron-Hernandez's attorney stating that the circumstances had 

changed: "You guys are going to have to tell him that the new 

offer will be higher based on the new case, if he insists on the 

13 years he is going to have to face two trials." 

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have been unduly optimistic, but we cannot say that his approach

falls short of professional competence on the record before us. 

See, e.g., Feliciano-Rodríguez, 986 F.3d at 37 (stating that 

deficient performance will be found "only where, given the facts 

known at the time, counsel's choice was so patently unreasonable 

that no competent attorney would have made it" (emphasis added) 

(quoting Knight v. Spencer, 447 F.3d 6, 15 (1st Cir. 2006))).

Notably, as described in our earlier discussion, Henwood 

did not dismiss Garcia's adjusted proposal out-of-hand at the 

September 28 meeting, an indication that Garcia's attempt to revive 

negotiations over that counteroffer -- or some offer lower than 

the original fifteen years/eight months (188 months) -- was not 

inevitably a non-starter. Indeed, Negron-Hernandez's attorneys 

apparently continued negotiating for a more favorable plea 

agreement covering the first indictment through early 2011, and 

the offer being discussed when the second indictment was issued (a 

defense recommendation of thirteen years (156 months) instead of 

fourteen years (168 months)) would have been more favorable to 

Negron-Hernandez than the government's original offer. See supra

note 21.22 In addition, one of the timing constraints that Henwood 

22 We recognize that the government may have been more willing 

to negotiate with Negron-Hernandez than with Torres-Estrada and,

indeed, the district court's docket indicates active plea 

negotiations for him through the fall. The district court granted 

a request to extend the deadline for Negron-Hernandez to complete 

plea negotiations until December 27, and his attorney subsequently 

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had imposed -- the entry of guilty pleas before the first trial in 

the case -- shifted shortly after Henwood told Granger the 

government's offer would not be lowered. Roughly a week after 

Henwood's communication, the late-October trial date was being 

reconsidered, and, on November 30, the court rescheduled the 

trial -- now including Torres-Estrada -- for March.

For the most part, then, Garcia's advice considered in 

isolation (apart from the contrary advice offered by Granger and 

Sapone) was not "so patently unreasonable that no competent 

attorney would have made it." Watson, 37 F.4th at 28 (quoting 

Tevlin, 621 F.3d at 66). Although Torres-Estrada emphasizes the 

conflict among his attorneys,23 neither the fact that Granger and

sought another extension to January 12, 2011. The latter motion 

was denied as moot in March after Negron-Hernandez entered into 

his consolidated plea agreement. Regardless of any differences in 

the government's approach to the two defendants, it is pertinent

in assessing Garcia's strategy that Negron-Hernandez's attorneys, 

like Garcia, continued efforts to obtain a more favorable plea 

deal on the first set of charges.

 

23 Torres-Estrada does not explicitly assert that Granger and 

Sapone advised him to accept the government's original offer in 

October 2010 after Henwood communicated the government's rejection 

of counteroffers. As Torres-Estrada had instructed -- at Garcia's

suggestion -- the two attorneys moved to withdraw from the case 

the day after Granger reported hearing from Henwood. However, we 

think a recommendation to accept the offer at that point is 

implicit in the guidance they did give -- i.e., that the original 

offers to Torres-Estrada and Negron-Hernandez were "excellent," 

that counteroffers were appropriate when the government's offers 

had not yet been described as final, and that time was of the 

essence in making a plea deal.

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Sapone disagreed with Garcia's advice nor Torres-Estrada's feeling

"confused and nervous" when faced with his attorneys' conflicting 

views means that Garcia's performance was deficient. By its 

nature, plea-bargaining can involve difficult choices: whether to 

take an offered plea, whether to make a counteroffer, and whether 

to reject a plea deal and leave one's fate in the hands of a jury. 

Torres-Estrada's decision on how to respond to the government's 

"final" offer inevitably would have been stressful even if he had 

only one defense attorney presenting him with the risks and 

advantages of various incompatible strategies similar to those 

presented by his multiple attorneys here.24

One aspect of Garcia's performance, however, requires 

particular attention: his repeated assurance that the government 

was still considering the specific counteroffer of thirteen 

years/six months (162 months). Torres-Estrada stated in his 

declaration that Garcia made that representation from the time he 

24 In making this observation, we note that the multipleattorney situation uniquely poses the possibility of conflicts

over defense strategy. We cannot anticipate what disagreements

may arise among members of a defense team, and we therefore speak 

only to the nature of the conflict that arose here. As we have 

described, Torres-Estrada faced competing, competent advice about 

the balancing of risk versus possible benefit that is an inherent

part of plea negotiations. Even if Garcia's disagreement with the 

lead attorneys made the choice of strategy more difficult than if 

one attorney had outlined various options, Torres-Estrada's

struggle nonetheless reflected only the typical predicament of

defendants weighing their options in plea negotiations rather than 

any deficiency in Garcia's performance.

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(Torres-Estrada) discharged the lead attorneys "until a few days 

before" he pleaded guilty. We found no evidence in the record of

ongoing consideration by the government of that specific 

counteroffer during that time period -- or, for that matter, any 

evidence of the government's response to Garcia's efforts to secure 

a better deal. In other words, the record lacks details on

Garcia's interactions with the government after Granger and Sapone 

withdrew.25 

Nevertheless, for the purpose of resolving the issue 

before us, we will assume favorably to Torres-Estrada that Garcia 

did misrepresent the state of the negotiations when he repeatedly 

indicated -- after Henwood had said that the government would not 

reduce its offer of fifteen years/eight months (188 months) --

25 Although the record does not reveal the government's 

bargaining position toward Torres-Estrada in the months after

Henwood reported in October 2010 that the government offer would 

not be reduced, there is evidence that the parties were engaged in 

plea negotiations during that period. In its response to TorresEstrada's pre-sentencing Lafler-Frye motion, the government stated 

that "[p]rior to the second indictment, the parties had been 

negotiating a plea that would have resolved [Torres-Estrada's] 

criminal liability" under the first indictment, and in its brief 

on appeal, the government described those negotiations as 

continuing until "the new criminal charges were imminent." The 

government also pointed out in its brief that "the same situation 

occurred with co-defendant" Negron-Hernandez and noted that his 

negotiations continued "even after October 2010." In addition, as 

recounted above, in a motion Garcia filed in February 2011 seeking 

to sever Torres-Estrada's case from those of the other defendants 

scheduled for trial the next month, Garcia stated that he "had 

been negotiating with the government to try to reach a plea 

agreement."

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that the government was still actively considering the thirteenyear/six-month (162-month) counteroffer that Garcia had made at 

the September 28 meeting with Henwood.26 Even if those

misrepresentations amounted to deficient performance,27 however,

Torres-Estrada could not satisfy the prejudice prong of his Sixth 

Amendment claim because the record shows that the statements, given 

their timing, had no impact on his loss of the government's offer.

That is to say, the timing of Garcia's comments relative 

to Torres-Estrada's decision-making ends up being critical to our

prejudice analysis. In describing his decision to sign onto 

Garcia's strategy in October 2010, Torres-Estrada said he did so 

after Garcia told him he "would be able to obtain a better deal" 

and that Garcia "would continue trying to obtain an offer of 162 

months' (13 years, 6 months') imprisonment." (Emphasis added.)

26 In making that assumption, we note that the government 

bears some responsibility for the lack of a more detailed record

on this issue, having argued to the district court that 

Torres-Estrada's § 2255 motion should be denied without an 

evidentiary hearing. Nor does the government in its brief to us 

provide its understanding of the status of the thirteen-year/sixmonth counteroffer after mid-October 2010 and before it suspended 

plea negotiations on the first indictment.

27 Although we raise the possibility of deficient performance 

based on Garcia's falsely telling his client that the thirteenyear/six-month counteroffer was under active consideration, we 

again note the significant differences from Frye and Lafler, where 

the attorneys either failed to convey a plea offer at all (Frye) 

or gave advice based on a mistaken understanding of the law 

(Lafler). Here, the assumed misrepresentation was limited to 

telling Torres-Estrada that the best-case outcome for the renewed 

plea negotiations was currently being considered.

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Garcia's stated goal, in other words, was to lower the government's 

original offer of fifteen years/eight months (188 months), ideally 

by resurrecting the thirteen-year/six-month (162-month) deal that 

Garcia had proposed at the September 28 meeting and that Henwood 

later rejected. But, despite Garcia's confidence about his 

negotiating ability, he made no claim that he could obtain that 

specific deal before Torres-Estrada decided in October 2010 to 

"follow[] Mr. Garcia's advice" to discharge Granger and Sapone and 

allow Garcia to continue negotiating. Hence, the record makes 

clear that Torres-Estrada's decision to forgo the government's 

offer at that time did not depend on the thirteen-year/six-month 

deal. Indeed, Torres-Estrada knew that the government had just 

rejected that counteroffer, and he thus necessarily understood

that any reconsideration of it by the government at that point 

would simply reflect Garcia's "trying to obtain" it.

According to Torres-Estrada, Garcia's

misrepresentations about the government's actual consideration of 

the thirteen-year/six-month counteroffer only began thereafter, 

i.e., "[f]rom the time that [Torres-Estrada] discharged 

. . . Granger and Sapone." Yet, by this point, Torres-Estrada had 

already made the decision to accept the risk of delaying acceptance 

of the government's offer based only on Garcia's assertion that he 

would be able to improve the government's offer, and not

necessarily by obtaining the previously rejected thirteenCase: 19-1485 Document: 00118223115 Page: 42 Date Filed: 12/06/2024 Entry ID: 6686123
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year/six-month deal. To be sure, Garcia's repeated 

representations about that deal may have amplified 

Torres-Estrada's hope that the government would agree to it. We 

cannot conclude, however, that Garcia's statements about the 

government's actual consideration of that counteroffer were the 

reason Torres-Estrada stuck with Garcia's strategy during the 

limited relevant timeframe -- i.e., from mid-October 2010, when 

Torres-Estrada chose Garcia's approach, and the point when the 

government decided to suspend negotiations on the first indictment 

in anticipation of the second indictment.28

Garcia's representations about the thirteen-year/sixmonth counteroffer during that period, even if misleadingly based 

on what he was seeking rather than on any signal from the 

government, were simply a version of the same over-confident claim

that had prompted Torres-Estrada to discharge Granger and Sapone

in the first place -- i.e., that Garcia would be able to negotiate 

a better deal for him than his lead attorneys and that he was

trying for the one he had proposed at the September 28 meeting. 

28 We think it likely that the government considered the new 

charges "imminent" by late December 2010 or early in January 2011. 

See supra note 25. We infer that timing from two facts: 

Negron-Hernandez received no response to his late December request 

to extend the deadline for his plea negotiations to January 12, 

and the second indictment was filed in early February. See id. 

The government states that it resumed negotiations after the second 

indictment "so that the parties could negotiate a consolidated 

plea agreement that would dispose of both cases."

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Torres-Estrada chose Garcia's aggressive strategy with no 

guarantee of its outcome, and despite explicit warnings from 

Granger and Sapone that delay could result in the government's 

withdrawing or increasing its offer for reasons that included the 

filing of new charges.29 We see no reasonable probability that, 

but for Garcia's repeated assurances that the government was 

deliberating about the specific thirteen-year/six-month proposal,

Torres-Estrada would have abandoned his commitment to Garcia's 

aggressive strategy -- and the goal of obtaining some better deal 

-- before the government's offer was off the table. See Frye, 566 

U.S. at 147 (explaining that ineffective-assistance-of-counsel 

claims premised on the loss of a more favorable plea deal require 

defendants to demonstrate, inter alia, "a reasonable probability" 

that they would have accepted the lower plea offer before "the 

prosecution cancel[ed] it"). Hence, even if Garcia's reports on 

the thirteen-year/six-month counteroffer misrepresented the status 

of that specific deal, Torres-Estrada has failed to show that those 

29 As noted, see supra Section I.B, Granger stated that the 

government's original plea offer included a verbal promise that it 

would not pursue new charges against Torres-Estrada. The 

government maintains that, even if the parties "agreed to the 

proposed terms in September of 2010, [Torres-Estrada] still would 

have faced a subsequent indictment." We need not dwell on the 

scope of Henwood's promise, however, because whether the 

government's original offer would have foreclosed the second 

indictment would be a pertinent issue only if Torres-Estrada could

show that he would have accepted that offer while it remained 

available.

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statements led to a less favorable sentencing outcome -- i.e., 

that he would have accepted the government's original offer before 

"the prosecution cancel[ed] it." Frye, 566 U.S. at 147.

***

In sum, we cannot conclude that Garcia's pleanegotiation performance amounted to "constitutionally deficient" 

representation that resulted in Torres-Estrada losing a more 

favorable plea deal than the one he ultimately obtained. Walker

v. Madeiros, 911 F.3d 629, 633 (1st Cir. 2018). We thus hold that 

Torres-Estrada has failed to show a violation of his Sixth 

Amendment rights and, accordingly, affirm the district court's 

denial of his request for sentencing relief.

So ordered.

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