United States Court of Appeals For the First Circuit

No. 19-1505

UNITED STATES OF AMERICA,

Appellee,

v.

LINCOLN GABRIEL PUPO,

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

Thompson, Lipez, Circuit Judges, and Laplante,* District Judge.

Andrew S. McCutcheon, Assistant Federal Public Defender, with whom Eric Alexander Vos, Federal Public Defender, and Franco L. Pérez-Redondo, Supervisor, Appeals Division, Assistant Federal Public Defender, were on brief, for appellant. Gregory B. Conner, 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 20, 2021

* Of the District of New Hampshire, sitting by designation. THOMPSON, Circuit Judge. Appellant Lincoln Gabriel Pupo

pleaded guilty to the federal crime of carjacking,

. Prior to his plea, he negotiated a deal with the

government stipulating a total offense level ("TOL") but not a

Criminal History Category ("CHC"). At sentencing, the district

judge calculated a higher TOL than the one in the plea agreement,

which together with the court's CHC calculation resulted in a

higher sentencing range than contemplated by the parties. Pupo,

citing procedural and substantive defects during sentencing,

requests that we vacate his sentence and remand for resentencing.

Perceiving no error, we affirm.

Background1

On January 15, 2018, two women returned to their parked

car after enjoying a meal at a Longhorn Steakhouse in Guaynabo,

Puerto Rico. As they settled into the car, Pupo approached the

driver's side window and ordered the pair to step out. Pupo made

his intentions clear, announcing that he was "assault[ing]" them

and that they should exit the vehicle immediately. Then he upped

the ante, telling them to get out of the car or else he would shoot

We draw the facts from the materials on appeal, 1

including the uncontested parts of the probation office's pre- sentence report ("PSR"), the plea colloquy, and the transcript of the relevant hearings. See United States v. Berrios-Miranda,

, 77 n.1 (1st Cir. 2019).

-2- them (though, unbeknownst to the pair, Pupo did not have a gun).

The two women complied, handed over the keys, and allowed Pupo to

drive off with the car. Soon thereafter, local law enforcement

located the vehicle and arrested Pupo. The two women identified

Pupo as their assailant. On January 18, 2018, a federal grand

jury charged Pupo with one count of carjacking, in violation of

. Pupo struck a deal with the government and pleaded

guilty to the sole offense.

Leading up to his sentencing hearing, both probation's

pre-sentence investigation and defense counsel's investigation

revealed that Pupo had a tough upbringing and suffered from

extensive substance abuse and mental health issues. Pupo came

from a dysfunctional home and grew up in several public housing

projects where violence pervaded. Living in an environment with

rampant drug use, he began using several controlled substances at

an early age. In 2011, a Puerto Rico Department of Corrections

social worker diagnosed him with mixed adjustment disorder,

anxiety, and depression while acknowledging a previous diagnosis

of bipolar disorder and ADHD. Most recently, in 2018, Pupo

underwent his first psychodiagnostics evaluation which revealed he

suffered from an unspecified form of Schizophrenia and "other

psychotic disorder." In his sentencing memorandum, Pupo attached

the psychodiagnostics evaluation and suggested that he needed both

-3- mental health and drug treatment, neither of which he had received

up to that point.

The PSR and Pupo's sentencing memorandum addressed his

difficult upbringing, substance abuse, and mental health issues in

detail. The two documents, however, diverged as to the

calculation of the Guidelines sentencing range ("GSR"). In his

sentencing memorandum, Pupo calculated a GSR of thirty-seven to

forty-six months' incarceration, using a CHC of III (even though

the parties did not stipulate to a CHC level) and relying on the

plea agreement's stipulated TOL of nineteen. Based on these

calculations, he sought a sentence of forty months' incarceration.

The PSR, however, calculated a total offense level of twenty-one

and a CHC of V, yielding a GSR of seventy to eighty-seven months

of imprisonment. Both the plea agreement and the PSR's

calculations included a base offense level of 20 under U.S.S.G.

§ 2B3.1, a two-point enhancement for the carjacking offense under

U.S.S.G. § 2B3.1(b)(5), and a three-point deduction for acceptance

of responsibility under U.S.S.G. § 3E1.1. But the PSR also

included an additional two-point "threat of death" enhancement

under U.S.S.G. § 2B3.1(b)(2)(F).2 Neither party objected to the

2The government had agreed not to include the threat of death enhancement in the plea agreement partly because Pupo represented that following incarceration he could seek mental health and substance abuse help in Florida near his family while

-4- PSR's calculations. In his sentencing memorandum, however, Pupo

did argue that although technically correct, the PSR's CHC

designation substantially over-represented the seriousness of his

criminal history and likelihood of recidivism and requested a

"downward departure" to category III.

At sentencing, defense counsel reiterated his request

for a downward departure after describing the way in which the

carjacking was a direct result of Pupo's long-standing mental

health and substance abuse issues, including his recent and first-

ever accurate diagnosis of an unspecified form of Schizophrenia

and "other psychotic disorder" -- all of which, again, was

presented in the PSR and sentencing memorandum. The government,

on the other hand, found the PSR's calculation of the CHC

appropriate, also noting that the court's responsibility to

protect the public from Pupo cautioned against a lower sentencing

range, but the government still stood by the total offense level

of nineteen from the plea agreement.

After reviewing the PSR, the addendum to the PSR, and

Pupo's sentencing memorandum, and after hearing from both parties,

the district court disagreed with Pupo's CHC assessment. The

district judge denied Pupo's request for a downward departure,

on supervised release.

-5- explaining that Pupo's "request for the Court to reconsider and

reevaluate the Criminal History Category . . . is being denied as

the Court finds [] that the probation officer has correctly

calculated the same." As an aside, the district judge mentioned

the "defendant's brushes with the law" which were "plenty and

numerous" and included multiple convictions, arrests, and

dismissed cases, but which did not factor into the CHC

calculation.3 Accordingly, the district judge adopted probation's

calculation, resulting in a GSR of seventy to eighty-seven months.

The district judge then considered the

(a) sentencing factors. Notably for this appeal, the judge

emphasized Pupo's history of mental health issues and "extensive

history of substance abuse." The district judge explained that

"because of [Pupo's] need for psychiatric medications and

consumption of drugs . . . he has reached stages in which his

mental illness predominantly is present, and has engaged in

numerous violations of the law." The district judge recognized

that "[t]his is Mr. Pupo's 12th known arrest and sixth conviction

The arrests and dismissed charges which the district 3

judge referred to included two counts of criminal contempt, one count of aggravated illegal appropriation in the fourth degree, two charges of conjugal abuse, two charges of threatening or intimidating a public authority, one charge of possession of controlled substances, one charge of damages, and two charges of possession of an edged weapon under the Puerto Rico Penal Code.

-6- as an adult," and emphasized his actions related to the offense

including the fact that "the victims felt and were submitted to

the threats and feared for their lives" and that they "were robbed

of the[ir] [] vehicle and belongings." The judge again recognized

that "the defendant needs treatment" for his mental health issues,

and that "he needs to remain committed to his medications and to

that treatment" because otherwise "he will not be able to control

[his actions]." Without medication, the district judge explained,

Pupo was a "time bomb." Finally, taking into consideration the

plea agreement, the need to promote respect for the law and to

protect the public from Pupo, as well as the need for deterrence

and punishment, the court sentenced Pupo to a term of seventy

months' imprisonment followed by three years of supervised

release.4

Defense counsel objected to the substantive and

procedural reasonableness of the sentence. Specifically, counsel

objected to the "Court's consideration of uncharged or dismissed

conduct" and the "denial of the request of downward departure based

on overrepresented criminal history and risk of recidivism, as

well as the arguments relating to Mr. Pupo's mental health." Pupo

The district judge also recommended that the Bureau of 4

Prisons provide mental health treatment and medication to Pupo and to designate him to a mental health institution or hospital facility within the Florida area.

-7- now appeals, alleging that his within-guidelines sentence is both

procedurally and substantively unreasonable.

Standard of Review

Claims challenging the procedural and substantive

reasonableness of a sentence are subject to a bifurcated inquiry:

"we first determine whether the sentence imposed is procedurally

reasonable" and if we conclude that it is, we "then determine

whether it is substantively reasonable." United States v. Flores-

Quiñones,

(1st Cir. 2021) (quoting United States

v. Reyes-Torres,

(1st Cir. 2020)); see also Gall

v. United States,

(2007). A sentence is

procedurally unreasonable when the district court commits a

procedural error such as "failing to calculate (or improperly

calculating) the Guidelines range, treating the Guidelines as

mandatory, failing to consider the § 3553(a) factors, selecting a

sentence based on clearly erroneous facts, or failing to adequately

explain the chosen sentence -- including an explanation for any

deviation from the Guidelines range." United States v. Díaz-

Rivera,

(1st Cir. 2020) (quoting United States v.

Bermúdez-Meléndez,

(1st Cir. 2016)).

A sentence is substantively reasonable if the

"sentencing court has provided a 'plausible sentencing rationale'

and reached a 'defensible result.'" Flores-Quiñones, 985 F.3d at

-8- 133 (quoting United States v. Sayer,

(1st Cir.

2019)). In determining the substantive reasonableness of a

sentence, we owe deference to the sentencing court's exercise of

informed discretion in fashioning the appellant's sentence.

United States v. López,

, 8-9 (1st Cir. 2020). Further,

"[i]n the sentencing context, we evaluate claims of

unreasonableness in light of the totality of the circumstances."

United States v. Flores-Machicote,

(1st Cir. 2013)

(citing Gall,

).

We review preserved claims of procedural and substantive

unreasonableness under the deferential abuse of discretion

standard, United States v. Dávila-Bonilla,

(1st Cir.

2020), reviewing findings of fact for clear error and issues of

law de novo, Bermúdez-Meléndez,

, ever cognizant

that the "touchstone of abuse of discretion review in federal

sentencing is reasonableness," United States v. Benoit,

, 24 (1st Cir. 2020) (quoting United States v. Vargas–Dávila,

(1st Cir. 2011)). We review unpreserved claims

of procedural unreasonableness for plain error. United States v.

Sánchez-Colberg,

(1st Cir. 2017).

Procedural Unreasonableness

Pupo asserts that the district judge committed three

procedural errors during his sentencing. We disagree.

-9- Pupo's first argument is that the district court failed

to meaningfully address his mental health diagnosis.5 According

to Pupo, the district court needed to specifically mention his

diagnosed mental illness, discuss how his illness related to the

§ 3553(a) factors, provide a reason why such a serious diagnosis

did not change the sentencing calculus, and give weight to his

5 The government posits that Pupo's arguments relating to his mental health and history of drug abuse are unpreserved. According to the government: Pupo did not explicitly object to the court's allegedly inadequate consideration of his substance abuse; his challenge related to his mental health was vague; and Pupo's mental health and substance abuse arguments before the district court were different than the ones before us now. The government, however, asks too much of Pupo. A party successfully preserves a claim of error for appeal by objecting with sufficient specificity so that the district court is aware of the claimed error. United States v. Castillo,

(1st Cir. 2020); see United States v. Rivera-Berríos,

(1st Cir. 2020) ("To preserve a claim of procedural sentencing error for appellate review, a defendant's objection need not be framed with exquisite precision."). Here, Pupo's sentencing memorandum clearly contended that he should receive a lower sentence because his comorbid conditions were mitigating factors cautioning against a prolonged period of incarceration. At sentencing, Pupo reiterated that the interaction of his substance abuse and mental health issues should engender leniency in the court's CHC determination and the overall sentence. Therefore, it would have been no surprise to the district court that when defense counsel objected to the procedural and substantive reasonableness of the sentence because of "the arguments relating to Mr. Pupo's mental health," he necessarily referred to the twin issues of his substance abuse and mental health struggles as they applied to his sentence. Further, by referencing those twin issues the district court was also on notice of Pupo's plea for leniency which consisted of both a lower CHC and a lower sentence, as described in the plea agreement, in the sentencing memorandum, at sentencing, and on appeal. Counsel's objections were adequate to preserve Pupo's claims before us.

-10- psychodiagnostics evaluation. Fatal to Pupo, his arguments do not

find support in this court's precedent nor in the record.

A district judge need not "verbalize its evaluation of

each and every [§] 3553(a) factor" nor do so in painstaking detail.

United States v. Contreras-Delgado,

(1st Cir.

2019) (alteration in original) (quoting United States v. Reyes-

Rivera,

(1st Cir. 2016)); see United States v.

Calderón-Lozano,

(1st Cir. 2019) ("The district

court . . . 'is not required to address [each] factor[ ], one by

one, in some sort of rote incantation when explicating its

sentencing decision.'" (quoting United States v. Dixon,

(1st Cir. 2006) (alteration in original))). At a minimum,

a district judge need only "say enough for us to meaningfully

review the sentence's reasonableness." United States v. Correa-

Osorio,

(1st Cir 2015).

The district court provided enough explanation here.

The district judge stated that she considered the § 3553(a)

factors, the PSR, and the sentencing memorandum which included

Pupo's psychodiagnostics report -- all of which recounted his

mental health and substance abuse issues and how they related to

a possible sentence. See Dávila-Bonilla, 968 F.3d at 12

(explaining that "the judge had read the defense's sentencing memo

and had heard the defense's leniency plea" thereby placing

-11- appellant's mitigation evidence "front and center"). Further, the

district court meaningfully considered Pupo's struggles with

mental health and substance abuse at sentencing. The court

repeatedly acknowledged his extensive history of substance abuse,

explained that comorbidity was related to his criminal history,

and acknowledged that Pupo was in need of treatment.

Additionally, the court specifically discussed sending Pupo to an

institution that had mental health facilities -- a clear

recognition that the judge understood that Pupo needed mental

health treatment. See Díaz-Rivera,

(noting that

the court's recommendation that defendant participate in drug

treatment program refuted appellant's allegation that the court

ignored his history of addiction). Unfortunately for Pupo, the

court did not weigh his criminal history and conditions in the

manner he had hoped. The district judge highlighted that he had

six convictions and that the facts of the present offense included

a serious threat of violence to the victims. Even further, the

district court made its view about Pupo's mental health and

substance abuse at the time of the offense abundantly clear: the

current combination of his untreated ailments rendered Pupo a "time

bomb." See United States v. Santa-Soler,

(1st

Cir. 2021) ("[I]t is incorrect to assume -- as the defendant does

-- that his failure to persuade the court to impose a more lenient

-12- sentence implies that the mitigating factors he cites were

overlooked."). With this explanation squarely before us, we

cannot say that the district court abused its discretion.

Next, Pupo asserts that the district court did not

adequately consider his need for mental health treatment or how to

implement treatment in the "most effective manner" as required by

(a)(2)(D).6 Had the court "completely disregarded

[this] sentencing factor[], this might be a different case . . .

however, the record makes manifest that the judge pondered [this]

sentencing factor . . . [and] simply came to a different, yet

altogether plausible, conclusion as to [its] salience." Dixon,

. The district judge explicitly referred to Pupo's

mental health and substance abuse struggles and explained how those

issues factored into the ultimate sentence. The district judge

even questioned defense counsel about Pupo's intention of living

in Florida with family following incarceration while receiving

treatment, expressing skepticism as to whether that arrangement

was workable. Finally, the district judge recommended Pupo to an

6Section 3553(a) requires a sentencing court to impose a sentence sufficient, but not greater than necessary, to achieve the purpose of sentencing. That sentence should, among other things, "provide the defendant with needed educational or vocational training, medical care, or other correctional treatment in the most effective manner." United States v. Rodriguez,

, 25 n.3 (1st Cir. 2013) (quoting

(a)(2)(D)).

-13- institution that would be able to assist him. Although federal

correctional institutions are not the standard-bearers for mental

health and substance abuse assistance, the court weighed Pupo's

needs with the need to protect society from further criminal

activity and arrived at a plausible result. Dixon,

; see United States v. Vélez-Soto,

(1st Cir.

2015).

Pupo's third challenge fares no better. He asserts that

the district court misunderstood its authority to depart

downwardly based on an overrepresented criminal history category

and improperly relied on arrests and charges that did not result

in convictions. The sentencing transcript suggests otherwise.

While it may be true that the district judge, in part, understood

defense counsel's request as a tardy objection to the PSR, the

district court also denied Pupo's "request for the Court to

reconsider and reevaluate the Criminal History Category" because

"the probation officer has correctly calculated the [CHC],"

signaling a straightforward denial of Pupo's departure request.

Moreover, directly after that statement, the district judge

squarely addressed the overrepresentation argument and rejected it

by concluding that Pupo's "brushes with the law are plenty and

numerous."

-14- Moreover, while Pupo correctly points out that we have

cautioned district judges against considering arrests not

buttressed by convictions or independent proof of conduct when

making an upward departure determination in United States v.

Marrero-Pérez,

(1st Cir. 2019), the record does

not suggest that the district judge "'equate[d] [his] arrest[s]

with guilt.' Nor . . . that the court relied solely on [Pupo's]

arrests or placed undue weight on either the arrests themselves or

their underlying conduct" -- our principal concerns in Marrero-

Pérez. Díaz-Rivera,

(internal citation omitted).

Of course, no error results when the district judge, as occurred

here, merely refers to the defendant's dismissed charges "'in the

course of relying on certain conduct that took place in connection

with the dismissed charges' and that conduct is described in

unchallenged portions of the [PSR]." United States v. Miranda-

Díaz,

(1st Cir. 2019) (quoting United States v.

Mercer,

(1st Cir. 2016)); United States v. Ramírez-

Romero,

(1st Cir. 2020).

Substantive Unreasonableness

Finally, Pupo avers that his sentence is substantively

unreasonable because the district judge failed to conduct a

"comprehensive sentencing assessment" and did not properly balance

the § 3553(a) factors. His position, however, is overwhelmingly

-15- refuted by the record because, as we explained above, the district

judge clearly articulated a plausible sentencing rationale and

reached a defensible result. The district judge reviewed the PSR

and sentencing memorandum, properly calculated his guidelines

sentencing range, and adopted probation's uncontested CHC

calculation. The district judge considered all the § 3553(a)

factors and discussed Pupo's mental health and substance abuse

struggles throughout the sentencing hearing. See United States

v. Daoust,

(1st Cir. 2018) (noting that an

explicit statement by the court that it considered all relevant

factors is entitled to significant weight). The district judge

also made it abundantly clear that Pupo's criminal history and the

underlying facts of the instant offense were troublesome,

concluding that Pupo was a "time bomb" who needed both treatment

and separation from society. Taken together, we cannot assign

error to a well-reasoned decision simply because the district judge

chose not to attach more weight to certain mitigating factors.

See United States v. Clogston,

(1st Cir. 2011)

("That the sentencing court chose not to attach to certain of the

mitigating factors the significance that the appellant thinks they

deserved does not make the sentence unreasonable."). This is

especially true where, like here, Pupo received a within-

-16- Guidelines sentence. See

The sentence, therefore, is

substantively reasonable.

Conclusion

For the foregoing reasons, we affirm.

-17-