Torres-Estrada v. United States

• Court: Court of Appeals for the First Circuit
• Decided: December 6, 2024
• Docket: 19-1485
• Status: Published

Opinion

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 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 decision-

making 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

- 2 - 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, Torres-

Estrada 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

The original indictment was filed in September 2009, and 1

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.

A superseding indictment filed in the second case in 2

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.

- 3 - 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.

- 4 - 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].

- 5 - 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

- 6 - 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

- 7 - 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

- 8 - 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

- 9 - 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 drug-

conspiracy 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

- 10 - 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

- 11 - 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 twelve-

and 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."

- 12 - 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 thirteen-

year/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

- 13 - 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

- 14 - 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

- 15 - 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 Torres-

Estrada, 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.

- 16 - 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.

- 17 - 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

10Torres-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.

- 18 - 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

Negron-Hernandez also signed a consolidated plea agreement 12

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.

- 19 - 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 fifteen-

year/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-four-

year (288-month) term of imprisonment recommended by the

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

have relied to describe the plea-bargaining process were submitted in connection with this motion.

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

counsel, including the second withdrawal of Granger and Sapone in January 2013.

- 20 - 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/eight-

month (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.

15With 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.

- 21 - 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

- 22 - 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.

- 23 - 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

- 24 - 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).

- 25 - 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

18As 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.

- 26 - 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).

- 27 - 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

- 28 - 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.

- 29 - 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

- 30 - 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 thirteen-

year 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

- 31 - 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 plea-

bargaining 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

- 32 - 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.

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

- 33 - 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

- 34 - 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

- 35 - 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."

- 36 - 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

22We 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

- 37 - 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.

Torres-Estrada does not explicitly assert that Granger and 23

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.

- 38 - 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

24In making this observation, we note that the multiple- attorney 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.

- 39 - (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 Torres- Estrada'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."

- 40 - that the government was still actively considering the thirteen-

year/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.)

26In 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/six- month counteroffer after mid-October 2010 and before it suspended plea negotiations on the first indictment.

Although we raise the possibility of deficient performance 27

based on Garcia's falsely telling his client that the thirteen- year/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.

- 41 - 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 thirteen-

- 42 - 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/six-

month 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.

28We 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."

- 43 - 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

29As 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.

- 44 - 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 plea-

negotiation 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.

- 45 -