United States v. Pupo, 995 F.3d 23

Background

On Jan. 15, 2018 Pupo threatened two women at a parked car (said he would shoot them though he had no gun), took their car, and was later arrested and charged with carjacking under 18 U.S.C. § 2119; he pleaded guilty pursuant to a plea agreement.
The plea agreement stipulated a Total Offense Level (TOL) of 19 but did not stipulate a Criminal History Category (CHC).
The PSR assessed a two-point §2B3.1(b)(2)(F) “threat of death” enhancement, raising the TOL to 21, and calculated CHC V (GSR 70–87 months); defense argued CHC III (GSR 37–46) and sought a downward departure.
Defense presented extensive mitigation: difficult upbringing, long history of substance abuse, and a psychodiagnostic evaluation diagnosing an unspecified schizophrenia/psychotic disorder and recommending treatment.
The district court adopted the PSR calculations, denied the downward-departure request, discussed Pupo’s mental-health/substance-abuse needs (called him a “time bomb”), recommended placement in a facility with mental-health services, and sentenced him to 70 months’ imprisonment plus three years supervised release.
Pupo appealed, arguing procedural and substantive unreasonableness based on the court’s consideration of mental-health evidence, treatment planning under §3553(a)(2)(D), and reliance on arrests/dismissed charges in denying a lower CHC.

Issues

Issue	Pupo's Argument	Government's Argument	Held
Whether the district court failed to meaningfully address Pupo's diagnosed mental illness	Court needed to expressly discuss the psychodiagnostic diagnosis, relate it to §3553(a) factors, and explain why it did not alter sentence	Court read and considered the sentencing memo/PSR (including psych report), discussed mental health repeatedly, and recommended a mental-health facility	No procedural error; court sufficiently considered mental-health evidence and explained its view
Whether the court failed to consider how to provide treatment in the "most effective manner" under §3553(a)(2)(D)	Court did not plan or implement concrete treatment arrangements and failed to weigh treatment need against incarceration	Court recognized treatment need, questioned post-release treatment plan, recommended BOP mental-health placement, and balanced treatment against public safety	No error; court considered §3553(a)(2)(D) and reached a plausible, defensible result
Whether the court improperly relied on arrests/dismissed charges or otherwise erred in refusing a downward departure for overrepresented criminal history	Court equated arrests with guilt and overrepresented CHC by citing dismissed/uncharged conduct	Probation correctly calculated CHC; the court did not rely solely on arrests and referenced unchallenged PSR conduct	No error; district court properly denied downward departure and did not improperly base decision solely on arrests
Whether the within-Guidelines sentence was substantively unreasonable	Sentence failed to balance §3553(a) factors and overstated mitigating weight of mental-health/substance-abuse evidence; higher TOL altered sentencing calculus	Court gave a plausible sentencing rationale, considered all §3553(a) factors, and imposed a within-Guidelines sentence	Substantively reasonable; appellate court defers to district court’s informed discretionary judgment

Key Cases Cited

Gall v. United States, 552 U.S. 38 (2007) (framework for procedural and substantive reasonableness review of sentences)
United States v. Flores-Quiñones, 985 F.3d 128 (1st Cir. 2021) (bifurcated inquiry: procedural then substantive reasonableness)
United States v. Díaz-Rivera, 957 F.3d 20 (1st Cir. 2020) (examples of procedural sentencing errors and limits on reliance on arrests)
United States v. Marrero-Pérez, 914 F.3d 20 (1st Cir. 2019) (caution against equating arrests with guilt for sentencing enhancements/departures)
United States v. Correa-Osorio, 784 F.3d 11 (1st Cir. 2015) (district court must "say enough" to permit meaningful appellate review)
United States v. Dixon, 449 F.3d 194 (1st Cir. 2006) (district court not required to address each §3553(a) factor in rote fashion)