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.
-2-

THOMPSON, Circuit Judge. Appellant Lincoln Gabriel Pupo 

pleaded guilty to the federal crime of carjacking, 18 U.S.C. 

§ 2119. 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 

1 We draw the facts from the materials on appeal, 

including the uncontested parts of the probation office's presentence report ("PSR"), the plea colloquy, and the transcript of 

the relevant hearings. See United States v. Berrios-Miranda, 919 

F.3d 76, 77 n.1 (1st Cir. 2019). 
-3-

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 18 

U.S.C. § 2119. 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 
-4-

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 

2 The 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 
-5-

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 firstever 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.
-6-

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 18 U.S.C. 

§ 3553(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 

3 The arrests and dismissed charges which the district 

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. 
-7-

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 

4 The district judge also recommended that the Bureau of 

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.
-8-

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. FloresQuiñones, 985 F.3d 128, 133 (1st Cir. 2021) (quoting United States

v. Reyes-Torres, 979 F.3d 1, 6-7 (1st Cir. 2020)); see also Gall

v. United States, 552 U.S. 38, 51 (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. DíazRivera, 957 F.3d 20, 25 (1st Cir. 2020) (quoting United States v. 

Bermúdez-Meléndez, 827 F.3d 160, 163 (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 
-9-

133 (quoting United States v. Sayer, 916 F.3d 32, 39 (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, 974 F.3d 1, 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, 706 F.3d 16, 20 (1st Cir. 2013) 

(citing Gall, 552 U.S. at 51). 

We review preserved claims of procedural and substantive 

unreasonableness under the deferential abuse of discretion 

standard, United States v. Dávila-Bonilla, 968 F.3d 1, 9 (1st Cir. 

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

law de novo, Bermúdez-Meléndez, 827 F.3d at 163, ever cognizant 

that the "touchstone of abuse of discretion review in federal 

sentencing is reasonableness," United States v. Benoit, 975 F.3d 

20, 24 (1st Cir. 2020) (quoting United States v. Vargas–Dávila, 

649 F.3d 129, 130 (1st Cir. 2011)). We review unpreserved claims 

of procedural unreasonableness for plain error. United States v. 

Sánchez-Colberg, 856 F.3d 180, 184 (1st Cir. 2017). 

Procedural Unreasonableness

Pupo asserts that the district judge committed three 

procedural errors during his sentencing. We disagree.
-10-

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, 981 F.3d 94, 101 (1st Cir. 2020); see United 

States v. Rivera-Berríos, 968 F.3d 130, 134 (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. 
-11-

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, 913 F.3d 232, 240 (1st Cir. 

2019) (alteration in original) (quoting United States v. ReyesRivera, 812 F.3d 79, 89 (1st Cir. 2016)); see United States v. 

Calderón-Lozano, 912 F.3d 644, 649 (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, 449 F.3d 

194, 205 (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. CorreaOsorio, 784 F.3d 11, 28-29 (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 
-12-

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, 957 F.3d at 28 (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, 985 F.3d 93, 99 (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 
-13-

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 

18 U.S.C. § 3553(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, 

449 F.3d at 205. 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 

6 Section 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, 731 

F.3d 20, 25 n.3 (1st Cir. 2013) (quoting 18 U.S.C. 

§ 3553(a)(2)(D)). 
-14-

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, 449 F.3d at 

205; see United States v. Vélez-Soto, 804 F.3d 75, 79-80 (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."
-15-

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, 914 F.3d 20, 22 (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 MarreroPérez. Díaz-Rivera, 957 F.3d at 27 (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. MirandaDíaz, 942 F.3d 33, 40 (1st Cir. 2019) (quoting United States v. 

Mercer, 834 F.3d 39, 50 (1st Cir. 2016)); United States v. RamírezRomero, 982 F.3d 35, 37 (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 
-16-

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, 888 F.3d 571, 576 (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, 662 F.3d 588, 593 (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-
-17-

Guidelines sentence. See id. The sentence, therefore, is 

substantively reasonable. 

Conclusion

For the foregoing reasons, we affirm.