United States v. Maldonado-Maldonado

134 F.4th 32

• Court: Court of Appeals for the First Circuit
• Decided: April 11, 2025
• Docket: 22-1650
• Status: Published

Opinion

United States Court of Appeals For the First Circuit

No. 22-1650

UNITED STATES OF AMERICA,

Appellee,

v.

HÉCTOR MALDONADO-MALDONADO,

Defendant, Appellant.

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

[Hon. Aida M. Delgado-Colón, U.S. District Judge]

Before

Gelpí, Lipez, and Rikelman, Circuit Judges.

José David Rodríguez, Research & Writing Specialist, with whom Rachel Brill, Federal Public Defender, District of Puerto Rico, Héctor L. Ramos-Vega, Interim Federal Public Defender, District of Puerto Rico, and Franco L. Pérez-Redondo, Assistant Federal Public Defender, Supervisor, Appeals Section, were on brief, for 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 appellee. April 11, 2025 RIKELMAN, Circuit Judge. In this sentencing appeal, the

government forthrightly concedes that it breached its plea

agreement with Héctor Maldonado-Maldonado ("Maldonado"). It also

admits that, as a result, we should vacate Maldonado's sentence.

We agree with the parties that, even under the plain error standard

that applies here, Maldonado has established that he is entitled

to resentencing because of the government's breach.

I. BACKGROUND1

A. Relevant Facts

In August 2020, Maldonado and one of his cellmates,

Miguel Santana-Avilés ("Santana"), were involved in an altercation

with a senior corrections officer (SCO) at the Metropolitan

Detention Center Guaynabo (MDC), where Maldonado was serving a

term of imprisonment. As the SCO was conducting a routine lockdown

procedure, he realized that Maldonado was not in his cell and

called out for him to return. The SCO also observed that the cell

contained a contraband item (an extra pillow). He removed the

pillow and walked out of the cell. At that point, Maldonado ran

back to his cell, yelling profanities at the SCO. When Maldonado

arrived, he punched the SCO in the face. Santana then grabbed the

Because this appeal follows a guilty plea, we draw the 1

relevant facts from the plea agreement, the unobjected-to portions of the Presentence Investigation Report, and the transcript of the sentencing hearing. See United States v. Colón-Cordero, 91 F.4th 41, 45 (1st Cir. 2024).

- 3 - SCO from behind and held his arms. When the SCO tried to extricate

himself, Maldonado put him in a headlock and continued to punch

his face, head, and neck. Other corrections officers quickly

arrived, pepper-sprayed both prisoners, and broke up the fight.

The SCO received medical treatment at MDC and was

subsequently transferred to the hospital for further evaluation

and treatment but was released after receiving medication. As a

result of the attack, the SCO sustained bodily injuries including

contusions to the face, ear, and hand. He also experienced pain

"during and after the assault" and recurring headaches, which

persisted until at least March 2022.

B. Procedural History

1. The Plea Agreement

Following these events, Maldonado and Santana were

indicted and charged with assaulting, resisting, or impeding a

federal officer. See 18 U.S.C. § 111(a)(1), (b). Maldonado

entered into a plea agreement, while Santana proceeded to trial.2

In the plea agreement, Maldonado and the government

proposed a sentencing calculation that resulted in a Total Offense

2 Santana was found guilty by the jury of "aiding andabetting, knowingly . . . forcibly assault[ing], imped[ing], intimidat[ing], or interfer[ing] with an officer of the United States while engaged in or on account of the performance of official duties." United States v. Santana-Avilés, 120 F.4th 7, 10 (1st Cir. 2024). He later appealed his conviction based on alleged evidentiary issues at trial. We rejected his arguments and affirmed his 87-month prison sentence. See id. at 10, 14.

- 4 - Level (TOL) of 13 under the United States Sentencing Guidelines.

See U.S. Sent'g Guidelines Manual §§ 2A2.4, 3E1.1 (U.S. Sent'g

Comm'n 2021) [hereinafter "U.S.S.G."]. The parties arrived at

this TOL as follows: a Base Offense Level (BOL) of 10 for

"[o]bstructing or [i]mpeding [o]fficers" pursuant to

section 2A2.4(a);3 a three-point enhancement pursuant to

section 2A2.4(b)(1) because the "offense involved physical

contact"; a two-point enhancement pursuant to section 2A2.4(b)(2)

because the "[v]ictim sustained bodily injury"; and a two-point

reduction for acceptance of responsibility pursuant to

section 3E1.1(a). The parties did not stipulate to a criminal

history category (CHC) for Maldonado, but the plea agreement

reflected that the guideline sentencing range for an individual

with CHC III would be 18-24 months.

The agreement also included a three-page stipulation of

facts describing the assault and the SCO's injuries. The

stipulation of facts did not mention that the SCO had any

difficulty breathing during the assault or elaborate upon

Maldonado's intent in putting the SCO in a headlock.

A BOL calculation under section 2A2.4 "incorporates the fact 3

that the victim was a governmental officer performing official duties." U.S.S.G. § 2A2.4(a) cmt. n.2.

- 5 - 2. The Presentence Investigation Report

Following Maldonado's guilty plea, the probation officer

prepared a Presentence Investigation Report (PSR). The PSR

included a markedly different guidelines calculation than the

calculation set out in the plea agreement. All told, the PSR

applied a 14-point "aggravated assault" BOL, thirteen points of

enhancements (many of which were not available under the plea

agreement's terms), and three points of reductions, for a TOL of

24.

In preparing the PSR, the probation officer relied on

facts presented at Santana's trial, which were not included in the

stipulation of facts in the plea agreement. Critically, these

facts led the probation officer to apply a different -- and more

punitive -- sentencing guideline than the one that the parties had

specified in their agreement. Referencing the SCO's testimony at

Santana's trial, the probation officer determined that "the

evidence [showed] that by placing the victim in a headlock,

[Maldonado] intentionally, knowingly, or recklessly impeded the

normal breathing . . . of the victim." She thus concluded that

Maldonado had "strangl[ed]" or "attempt[ed] to strangle" the SCO,

and therefore applied the "aggravated assault" guideline,

section 2A2.2(a), via the cross-reference at section 2A2.4(c)(1).

See U.S.S.G. § 2A2.2 cmt. n.1. Applying the "aggravated assault"

guideline led her to recommend a BOL of 14.

- 6 - The probation officer also recommended three additional

sentencing enhancements that were available under the "aggravated

assault" guideline but not the "impeding officers" guideline

contemplated by the plea agreement. To start, she added a

six-point "Official Victim" enhancement. Id. § 3A1.2(c)(2); see

also id. § 3A1.2 cmt. n.4(A) (explaining that the enhancement

applies "in circumstances tantamount to aggravated assault"). She

also added another two-point enhancement related to the SCO's

status as a federal officer. See id. § 2A2.2(b)(7) (enhancement

for assaulting a federal officer under 18 U.S.C. § 111). And she

added a further two-point enhancement because the SCO had been

"physically restrained." Id. § 3A1.3.

The PSR, like the plea agreement, also included a "bodily

injury" enhancement. See id. § 2A2.2(b)(3)(A). However, the PSR's

three-point "bodily injury" enhancement was one point higher than

the similar enhancement calculated under the plea agreement's

recommended guideline. Nevertheless, the probation officer did

not recommend an enhancement for "serious bodily injury," even

though it was available under the "aggravated assault" guideline

she had applied. Finally, the probation officer also applied a

three-point reduction for Maldonado's acceptance of

responsibility. See id. § 3E1.1(a)-(b).

Maldonado submitted timely objections to the PSR. In

particular, he objected to the probation officer's use of the

- 7 - "aggravated assault" guideline to calculate his BOL. He explained

that "the determination of whether or not an aggravated assault

took place requires the court to find facts [that] Mr. Maldonado

disputes and [to which he] has not stipulated." He also explained

that the SCO had raised accusations of strangulation for "the first

time" at Santana's trial. Finally, he objected to the related

enhancements the probation officer had included -- which were

available only under the "aggravated assault" guideline -- based

on the SCO's status as an "official" and the use of "physical[]

restrain[t]." Maldonado reiterated these arguments in the

sentencing memorandum that he filed in advance of the sentencing

hearing.

3. The Government's Sentencing Memorandum

The government then filed its own sentencing memorandum.

Like the PSR, the government's sentencing memorandum relied on the

SCO's testimony at Santana's trial. Citing that testimony, the

government described Maldonado's conduct as a "vicious assault"

that resulted in "physical and prolonged emotional injuries" to

the SCO. It explained that there was a "paramount" need to deter

Maldonado from future "assaultive behavior." The government

- 8 - concluded its memorandum by requesting a sentence of 24 months,

the upper end of the range in the plea agreement.

4. The Sentencing Hearing

The district court held a sentencing hearing on August

4, 2022. The prosecutor began the hearing by deviating from the

guidelines calculation set out in the plea agreement and the

government's own sentencing memorandum. Specifically, the

prosecutor argued for a "level four enhancement for th[e] bodily

injury" sustained by the SCO, which he contended met the "serious

bodily injury" standard in the "aggravated assault" guideline used

in the PSR. See U.S.S.G. § 2A2.2. Importantly, however, the

"serious bodily injury" enhancement was not available under the

"impeding officers" guideline specified in the plea agreement.

See id. § 2A2.4. Maldonado therefore objected to the "serious

bodily injury" enhancement and advocated instead for a lower

enhancement for "bodily injury" only.4 The district court declined

to apply the four-point "serious bodily injury" enhancement and

determined that a three-point enhancement was appropriate.

The district court then asked about Maldonado's

objection to the discrepancy between the 10-point BOL in the plea

agreement and the 14-point BOL in the PSR. Defense counsel

4 The plea agreement contained a two-point enhancement for "bodily injury." But at the sentencing hearing, defense counsel seemed to agree with the court that a three-point bodily injury enhancement was appropriate.

- 9 - explained that there were "no statements, no other behavior, [and]

no other circumstantial evidence" on the record as to Maldonado's

intent to strangle or otherwise impede the SCO's breathing -- and

so the "aggravated assault" guideline and its associated 14-point

BOL were inapplicable. The district court disagreed. It concluded

that, after considering the evidence introduced at trial, the

"aggravated assault" guideline was warranted.

After Maldonado's allocution, the district court asked

to hear from the prosecutor once more. The prosecutor proceeded

to describe the assault as "exceedingly dangerous,"

"extraordinary," and "intentional, aggressive, violent, [and]

heinous." He also described Maldonado as "inherent[ly]

dangerous[]," which he said was "a statement that is completely

supported by the evidence in this case." Finally, he concluded

that "to the extent that there are factual inconsistencies" between

Maldonado's account and the government's, the court should be "the

final arbiter of those facts." The prosecutor did not make any

explicit recommendation as to the appropriate sentence but rather

directed the court to the government's "position in" the sentencing

memorandum it had previously filed.

The district court proceeded to adopt the PSR's

sentencing guidelines calculation in full. It then sentenced

Maldonado, based on a TOL of 24 and a CHC of III, to 78 months in

- 10 - prison, the upper end of the PSR's sentencing guidelines range.

He is currently set to be released on February 10, 2027.

Maldonado timely appealed his sentence.5

II. DISCUSSION

Maldonado asks us to vacate his sentence for two separate

reasons: (1) the prosecutor's breach of the plea agreement, and

(2) the district court's reliance at the sentencing hearing on

extra-record facts. Given the government's concession that a plea

breach occurred, we do not reach Maldonado's second argument.

A. Standard of Review

Because Maldonado "did not assert that the government

breached the plea agreement during the sentencing proceedings, our

review is for plain error." United States v. Acevedo-Osorio, 118

F.4th 117, 127 (1st Cir. 2024). Under the plain error standard,

Maldonado must show "(1) that an error occurred (2) which was clear

or obvious and which not only (3) affected [his] substantial

rights, but also (4) seriously impaired the fairness, integrity,

or public reputation of judicial proceedings." Id. (quoting United

States v. Cheveres-Morales, 83 F.4th 34, 42-43 (1st Cir. 2023)).

5 Although the plea agreement contained a waiver-of-appeal provision, the district court sentenced Maldonado above the agreed-upon range of 18-24 months. Thus, the waiver provision does not bar his appeal.

- 11 - B. Breach of the Plea Agreement

Maldonado contends that the government breached the plea

agreement in four ways: (1) by advocating for a four-point

sentencing enhancement for "serious bodily injury" when the plea

agreement expressly contemplated only a two-point enhancement for

"bodily injury"; (2) by "tacitly push[ing]" for the application of

the aggravated assault guideline, given that the four-point

"serious bodily injury" enhancement and the other enhancements

recommended in the PSR were available only if that guideline

applied; (3) by failing to affirmatively request an 18-24 month

sentence; and (4) by failing to object to the PSR's recommended

sentence. The government concedes that "looking at the

[prosecutor's] holistic approach [and] overall performance," it

breached the plea agreement.

We agree that the government breached the plea agreement

and that its breach was clear and obvious, satisfying the first

two prongs of the plain error standard. As we have explained,

prosecutors are held to "the most meticulous standards of both

promise and performance" in executing plea agreements. United

States v. Almonte-Nuñez, 771 F.3d 84, 89 (1st Cir. 2014) (quoting

United States v. Riggs, 287 F.3d 221, 224 (1st Cir. 2002)). "Such

standards require more than lip service to, or technical compliance

with, the terms of a plea agreement." Id. Thus, we have

"prohibit[ted] not only explicit repudiation of the government's

- 12 - assurances, but [also] . . . end-runs around them." United States

v. Canada, 960 F.2d 263, 269 (1st Cir. 1992) (quotation marks and

citation omitted).

As the government commendably acknowledges, "[b]y

advocating for a greater ['serious bodily injury'] enhancement,

the prosecutor undermined the benefit of the plea agreement." See

United States v. Matos-Quiñones, 456 F.3d 14, 24 (1st Cir. 2006)

("A defendant is entitled . . . to the benefit of the bargain

struck in the plea deal and to the good faith of the prosecutor."

(cleaned up)). That advocacy plainly ran afoul of the parties'

plea deal because, as the government explains, "the guideline

proposed in the plea agreement did not [permit] a four-level

enhancement for injury." Thus, with its request for this

particular enhancement, "the prosecutor implicitly advocated for

the use of the aggravated assault guideline." And the "aggravated

assault" guideline opened the door to other sentencing

enhancements, such as the six-point "Official Victim" enhancement,

that contradicted the terms of the parties' agreement.

Further, the prosecutor described the assault as

"extraordinary," "heinous," and "violent." As we have held, by

using terms like "extraordinary" or "exceptional," the government

"impermissibly signal[s]" that the defendant's case falls outside

the "guidelines' heartland" or the "mine-run" of cases. United

States v. Mojica-Ramos, 103 F.4th 844, 851-52 (1st Cir. 2024)

- 13 - (quotation marks and citation omitted). So the prosecutor's

language, coupled with the express request for the "serious bodily

injury" enhancement, undermined the very basis for the sentence

contemplated by the parties in the plea agreement. For these

reasons, Maldonado is correct on his first two plea breach

arguments, and the government does not contend otherwise.6

What is more, the government does not dispute that the

cumulative errors we have described had a substantial effect on

Maldonado's rights and impaired the fairness of his sentencing

hearing. Thus, all four prongs of the plain error standard are

met, and Maldonado is entitled to resentencing.

C. Remedy

The parties disagree, however, on the scope of the remedy

for the government's breach. The government contends that

remanding to a different judge for resentencing is a sufficient

and appropriate remedy. Maldonado, for his part, would have us

remand to a different judge with specific instructions that the

district court impose a sentence within the range provided by the

plea agreement. But he is not entitled to such "extraordinary"

relief. United States v. Kurkculer, 918 F.2d 295, 299 (1st Cir.

1990).

6The government nevertheless argues that Maldonado's third and fourth points do not make out claims for breach under our case law and thus do not provide "independent bases for remand."

- 14 - To be sure, Maldonado is entitled to specific

performance by the government of its promises in the plea

agreement. And to its credit, the government has assured us that

it will fulfill its obligations. At oral argument, it represented

that "no [sentencing] argument" by it concerning "any aggravating

factors would be relevant" on remand. It also acknowledged that

the only way for it to adhere in "good faith" to the plea agreement

would be for the prosecutor to recommend a sentence of 18-24

months. Acevedo-Osorio, 118 F.4th at 129. And given that

Maldonado has already served 32 months, the government's

anticipated recommendation for 18-24 months will amount to a

request for a sentence of time served.

To the extent Maldonado contends that the government's

breach entitles him to a specific sentence from the district court,

however, we disagree.7 The obligation of specific performance of

the plea agreement runs against the government, not the district

court. Further, the plea agreement did not bind the district court

to adopt the parties' recommended sentencing range. See Fed. R.

Crim. P. 11(c)(1)(A)-(B). Maldonado nevertheless argues that the

only adequate remedy here would be a remand with directions to

impose a sentence that results in his immediate release; that is

7 Indeed, by signing the agreement, Maldonado bargained only for the "possibility that the judge could choose to act in accordance with the [agreement's] recommendation." Kurkculer, 918 F.2d at 299.

- 15 - so, he claims, because he has already served more time in prison

than the high end of the sentencing range specified in the plea

agreement and thus has lost all "possibility" of receiving the

sentence contemplated by the parties. Kurkculer, 918 F.2d at 299.

But a decision on our part to exercise our equitable power to

"depriv[e] the trial court of its discretion in sentencing" would

be "extraordinary," and such an extraordinary remedy is only to be

considered in the very rarest of circumstances. Id.; accord

Mojica-Ramos, 103 F.4th at 854. Such circumstances are not present

here.

Kurkculer, on which Maldonado relies to argue otherwise,

is readily distinguishable.8 There, the defendant strenuously

objected during the sentencing hearing to the prosecutor's breach

(and was penalized for his objections in the form of additional

sentencing enhancements), had served almost double the sentence

the government had agreed to recommend by the time of our decision

in his appeal, and was scheduled for release "soon." Kurkculer,

918 F.2d at 296-98, 302. We therefore concluded that the only way

for the defendant to obtain any remaining benefit from his

agreement with the government was by exercising our equitable power

to direct the district court to impose a time-served sentence on

8By our review, Kurkculer is one of only two cases in which we have exercised our equitable power to direct a specific sentence on remand. See 918 F.2d at 301; Correale v. United States, 479 F.2d 944 (1st Cir. 1973).

- 16 - remand. See id. at 302. By contrast, given that Maldonado is not

scheduled for release until February 2027, a new sentencing hearing

in which the government scrupulously follows its obligations in

the plea agreement could still provide him the possibility of a

significantly reduced sentence. That is particularly so because

we have every confidence that the parties will cooperate to ensure

a prompt re-sentencing.

Accordingly, following "well-settled precedent," United

States v. Clark, 55 F.3d 9, 14 (1st Cir. 1995), and "in accordance

with our normal practice upon finding prosecutorial breach, we

remand . . . for resentencing before a different judge,"

Mojica-Ramos, 103 F.4th at 854 (quotation marks and citation

omitted). In remanding with these instructions, "[w]e emphasize

that this is in no sense to question the fairness of the sentencing

judge; the fault here rests on the prosecutor, not on the

sentencing judge." Santobello v. New York, 404 U.S. 257, 263

(1971).

III. CONCLUSION

For all these reasons, we vacate Maldonado's sentence

and remand for expedited resentencing before a different district

court judge.

- 17 -