United States v. Perry

Decision Date16 September 2022
Docket Number21-1730
Citation49 F.4th 33
Parties UNITED STATES of America, Appellee, v. Damian PERRY, a/k/a Primo, Defendant, Appellant.
CourtU.S. Court of Appeals — First Circuit

James M. Mason, with whom Handelman & Mason LLC was on brief, for appellant.

Mahogane D. Reed, U.S. Department of Justice, Criminal Division, Appellate Section, with whom Darcie N. McElwee, United States Attorney, Joel B. Casey, Assistant United States Attorney, Kenneth A. Polite, Jr., Assistant Attorney General, and Lisa H. Miller, Deputy Assistant Attorney General, were on brief, for appellee.

Before Thompson, Howard, and Gelpí, Circuit Judges.

THOMPSON, Circuit Judge.

Damian Perry (known to some as "Primo") questions the procedural and substantive reasonableness of a below-guidelines sentence imposed by a federal district judge in Maine. But we must affirm.

How Perry Got Here

Perry's story bounces back and forth between Connecticut and Maine. Noting only what is needed to frame the legal issues before us, we ask for the reader's patience as we provide the key dates and details (their significance will become clear later, rest assured — know too that the core background events are undisputed unless otherwise noted).

Sometime in early 2016, Perry hooked up with Luis Padilla. It changed Perry's life forever.

Padilla led a gang that dumped drugs (crack and heroin) from Connecticut onto the streets of Maine. Doing what he could to help the group, Perry (in the government's telling) soon became co-leader with Padilla (Perry contests the co-leader label). Authorities caught on to their activities, however. And by 2016's end, a federal grand jury in Connecticut indicted the two and another on various drug charges — including conspiracy from about October 1, 2016 through October 12, 2016.

Perry got released on bail after his arrest, conditioned on his not breaking any laws (federal, state, or local). And in March 2017, he pled guilty in Connecticut federal court to the conspiracy charge. But he did not stay out of trouble for long. We know this because while still on bail pending sentencing in Connecticut, he got busted in September 2017 for pumping more drugs into Maine.

Cut to July 2018. A federal grand jury in Maine indicted Perry, Padilla, and others for drug conspiracy (involving crack and heroin) beginning about January 1, 2015 and continuing to about September 1, 2017. Back in Connecticut, however, a federal district judge about a month later — after factoring his "continu[ing] to commit crimes" during the bail period into her decisional calculus, see 18 U.S.C. § 3553(a) (a statute that guides judges during sentencing) — gave Perry 92 months behind bars for his part in the conspiracy charged in the Connecticut case, with 92 months being the lowest point on the guidelines range (granting the government's motion, the Connecticut federal judge also tossed the remaining counts). Padilla got 78 months for his role.

April 2019 turned out to be a good month for Padilla, however. A federal district judge in Maine dismissed the case against him there for double jeopardy, concluding that the government "failed to show it is not prosecuting [him] twice for the same crime." But a little later, in May 2019, a Maine federal grand jury separately indicted Perry for possessing drugs (crack and heroin) with intent to distribute and for using a communications device to commit a drug crime (a big difference between this indictment and the other indictments is that this one did not include a conspiracy charge). In July that same year, Perry pled guilty to these counts in return for the government's dismissal of the conspiracy charge in the earlier Maine federal indictment.

That brings us to Perry's sentencing on the drug-distribution and communications-device counts. During that time, a lot happened. But all one needs to know for now appears in the next seven paragraphs.

As the calendar turned to November 2019, a probation officer drafted a presentence investigation report ("PIR") using conduct — including drug quantities — from Perry's Connecticut-conspiracy conviction to develop a guidelines range. Perry objected to some parts of the PIR in January 2020, arguing for example that probation's use of that conduct raised double-jeopardy concerns because it was "implicated" in the Connecticut case.1 Which explains why he asked the Maine federal judge not to use drug weight from that conviction (he thought, and still thinks, however, that double-jeopardy principles "should be considered when determining the fairness of the sentence and whether the sentence in the Maine case should run concurrent to that of the Connecticut case). Having had some time to think about the matter, that same judge — at a presentence conference in April 2020 — asked probation to tell the parties what Perry's guidelines range would be with his Connecticut-offense conduct removed from the equation.

Released in July 2020, probation's revised PIR laid out the two scenarios.

Scenario one: The Maine federal judge treats Perry's Connecticut offense as "relevant conduct" to the drug-distribution and communications-device violations listed in the Maine federal indictment. See USSG § 1B1.3(a)(1)(B) (defining relevant conduct to include "all acts and omissions" (1) "within the scope of the jointly undertaken criminal activity"; (2) "in furtherance of that criminal activity"; and (3) "reasonably foreseeable in connection with that criminal activity"). So all drug quantities from the Connecticut case get added to the mix, resulting in a base offense level of 32. After some adjustments (not relevant here), the total-offense level becomes 38. The Connecticut offense does not affect his criminal-history category of V, however. Perry's guidelines range is 360 months to life, though statutorily capped at 528 months. Treating the Connecticut offense as relevant conduct means the Maine federal judge could adjust Perry's sentence to run fully concurrent with his Connecticut-offense sentence. See USSG § 5G1.3(b)(2) (providing that if "a term of imprisonment resulted from another offense that is relevant conduct to the instant offense ... the sentence for the instant offense shall be imposed to run concurrently to the remainder of the undischarged term of imprisonment"); see also id. § 5G1.3(b)(1) (stating that if the judge concludes that the bureau of prisons will not credit time "already served on the undischarged term of imprisonment," the judge "shall adjust the sentence" to account for that time).

Now for scenario two, which differs dramatically from scenario one: The Maine federal judge does not treat Perry's Connecticut offense as relevant conduct. So all drug quantities from that case are excluded from the sentencing calculation, which results in a base-offense level of 28 and an adjusted total-offense level of 34. This scenario also triggers the addition of 3 criminal-history points, placing Perry in criminal-history category VI with a guidelines range of 262 to 327 months. And not considering the Connecticut offense as relevant conduct means the Maine federal judge could run Perry's sentence concurrent with, partially concurrent with, or consecutive to the undischarged Connecticut-offense sentence. See USSG § 5G1.3(d) (policy statement) (providing that if a prior offense is not relevant conduct to the instant offense, the judge may impose a sentence concurrent, partially concurrent, or consecutive "to the prior undischarged term of imprisonment").

Returning to his theory of double jeopardy, Perry insisted that the Connecticut federal judge had already punished him for his conduct and so the Maine federal judge had to impose a sentence fully concurrent to his Connecticut sentence.2 But the Maine federal judge concluded otherwise in December 2020, ruling that enhancing (within statutory limits) the punishment for Perry's latest crime because of earlier criminal conduct would not impose a second punishment for that conduct. "[T]he tail of" the relevant conduct from the Connecticut case, said the judge, is not "wag[ging] the dog of the substantive offense[s]" in Maine.

As Perry's sentencing drew nearer, he and the government jointly stipulated in March 2021 that before his December 2016 arrest "in Connecticut, [he] had been participating in a drug trafficking conspiracy with Luis Padilla and others since 2016" and that "[a]t some point following his release following his arrest in Connecticut" he "resumed his participation in the conspiracy" (some brackets removed). But at sentencing in September 2021, the parties agreed that in crafting the guidelines range the Maine federal judge should exclude all drug quantities charged in the Connecticut case. That judge accepted their agreement, noting that omitting those quantities helps "lower" the guidelines range. The judge then applied a 3-level enhancement because Perry committed new crimes while on bail, see USSG 3C1.3, rejecting his double-jeopardy theory that the Connecticut federal judge had "punished [him] already for this bail violation in his Connecticut case." And the judge added 3 criminal-history points for the Connecticut conviction, putting Perry in criminal-history category VI with a guidelines range of 262 to 327 months.

Beneficially to Perry, however, the Maine federal judge used a range of 210 to 262 months to reduce the sentencing disparity between crack and powder cocaine. And after assessing the § 3553(a) factors, the judge varied downwards (by a lot) to 137 months — with 6 months attributed to Perry's having done the underlying offenses while on bail. Last (though not least), the judge structured Perry's term to run concurrently with the rest of the Connecticut sentence but with no credit for the 48 months already served on that sentence. The judge ruled that way after rebuffing Perry's claim that sentencing delays caused by the COVID-19 pandemic represent the kind of "extraordinary" circumstances that justify time-served credit and after saying...

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