United States v. Pupo

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, 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
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, 919
F.3d 76, 77 n.1 (1st Cir. 2019).
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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
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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
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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.
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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
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.
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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.
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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, 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. Díaz-
Rivera, 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
-8-
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.
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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.
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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. Reyes-
Rivera, 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. Correa-
Osorio, 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
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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
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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
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, 731
F.3d 20, 25 n.3 (1st Cir. 2013) (quoting 18 U.S.C.
§ 3553(a)(2)(D)).
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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."
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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 Marrero-
Pérez. 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. Miranda-
Díaz, 942 F.3d 33, 40 (1st Cir. 2019) (quoting United States v.
Mercer, 834 F.3d 39, 50 (1st Cir. 2016)); United States v. Ramírez-
Romero, 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
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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-
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Guidelines sentence. See id. The sentence, therefore, is
substantively reasonable.
Conclusion
For the foregoing reasons, we affirm.
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