United States v. Key ( 2023 )

22-337
United States v. Key
UNITED STATES COURT OF APPEALS
FOR THE SECOND CIRCUIT
SUMMARY ORDER
Rulings by summary order do not have precedential effect. Citation to a summary order filed on
or after January 1, 2007, is permitted and is governed by Federal Rule of Appellate Procedure 32.1
and this court’s Local Rule 32.1.1. When citing a summary order in a document filed with this
court, a party must cite either the Federal Appendix or an electronic database (with the notation
“summary order”). A party citing a summary order must serve a copy of it on any party not
represented by counsel.
At a stated term of the United States Court of Appeals for the Second Circuit,
held at the Thurgood Marshall United States Courthouse, 40 Foley Square, in the
City of New York, on the 20th day of June, two thousand twenty three.
PRESENT: Denny Chin,
Steven J. Menashi,
Circuit Judges,
Paul A. Engelmayer,
District Judge. *
____________________________________________
UNITED STATES OF AMERICA,
Appellee,
v. No. 22-337
ROGER KEY, ALSO KNOWN AS SEALED
DEFENDANT 1, ALSO KNOWN AS LUCHIE,
Defendant-Appellant. †
____________________________________________
*Judge Paul A. Engelmayer of the United States District Court for the Southern District of New
York, sitting by designation.
† The Clerk of Court is directed to amend the case caption as set forth above.
For Appellee: LISA DANIELS, Assistant United States
Attorney (Hagan Scotten, Assistant United
States Attorney, on the brief), for Damian
Williams, United States Attorney for the
Southern District of New York, New York,
NY.
For Defendant-Appellant: BRUCE R. BRYAN, Manlius, NY.
Appeal from a judgment of the United States District Court for the Southern
District of New York (Stein, J.).
Upon due consideration, it is hereby ORDERED, ADJUDGED, and
DECREED that the judgment of the district court is AFFIRMED.
Roger Key was convicted of crimes including conspiracy to commit murder-
for-hire, conspiracy to distribute and possess with intent to distribute narcotics,
and attempted murder-for-hire. Key was sentenced to life imprisonment and a
consecutive term of thirty years’ imprisonment. This court vacated one count of
Key’s convictions in light of United States v. Davis, 139 S. Ct. 2319 (2019), and we
remanded to the district court for resentencing. Order, Key v. United States, No. 19-
2169 (2d Cir. Nov. 4, 2020), ECF No. 94. The district court conducted a de novo
resentencing, leading to a new sentence of forty-five years’ imprisonment and
forfeiture in the amount of $16.2 million.
Key raises three challenges to his sentence. First, he argues that this new
sentence is substantively unreasonable. Second, he argues that the district court
improperly structured his sentence. Third, he argues that the district court erred
in ordering forfeiture. We disagree with Key’s arguments and affirm the judgment
of the district court. We assume the parties’ familiarity with the underlying facts
and procedural history.
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I
Key makes both a substantive unreasonableness challenge and a procedural
unreasonableness challenge to his sentence. We address these challenges in turn.
A
We “consider the substantive reasonableness of the sentence imposed under
an abuse-of-discretion standard.” Gall v. United States, 552 U.S. 38, 51 (2007). A
defendant “bears a heavy burden because our review of a sentence for substantive
reasonableness is particularly deferential.” United States v. Broxmeyer, 699 F.3d 265,
289 (2d Cir. 2012). “That deference derives from a respect for the distinct
institutional advantages that district courts enjoy over their appellate counterparts
in making an ‘individualized assessment’ of sentence under 18 U.S.C. § 3553(a).”
Id. (quoting Gall, 552 U.S. at 50). In particular, “it is difficult to find that a below-
Guidelines sentence is substantively unreasonable.” United States v. Rivernider, 828
F.3d 91, 111 (2d Cir. 2016) (internal quotation marks and alteration omitted).
Key argues that the district court insufficiently considered certain factors
that—in Key’s view—justify an even more lenient sentence than the below-
Guidelines sentence he received. Following the vacatur of one count of Key’s
conviction, Key remained convicted of the following five counts: conspiracy to
distribute and possess with intent to distribute narcotics, in violation of 21 U.S.C.
§ 846 and § 841(b)(1)(A); using and carrying firearms during and in relation to that
narcotics offense, in violation of 18 U.S.C. § 924(c); conspiracy to commit murder
for hire, in violation of 18 U.S.C. § 1958; attempted murder for hire, in violation of
18 U.S.C. § 1958; and a second conspiracy to commit murder for hire, in violation
of 18 U.S.C. § 1958. In Key’s view, his forty-five-year sentence—though reduced
from his initial sentence of life imprisonment plus thirty years—was substantively
unreasonable because (1) he has made successful efforts toward rehabilitation in
prison, (2) the sentence unreasonably punishes his family members who are
experiencing extraordinary hardship, (3) he will be at a lower risk of recidivism
after serving the mandatory minimum of twenty years, (4) the sentence created an
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unwarranted sentencing disparity between co-defendants in this case, (5) a
lengthy period of incarceration will not further his rehabilitation, and (6) his
incarceration during the COVID-19 pandemic constituted extraordinary
punishment. We disagree.
The district court considered the factors set forth in 18 U.S.C. § 3553(a) and
varied below the applicable Guidelines sentence. The district court calculated the
recommended sentence under the Guidelines to be life imprisonment plus five
years. The district court nevertheless sentenced Key to forty-five years’
imprisonment because, in its view, Key “deserves to be able to look forward to
getting out of prison and not to have spent his life in prison” and Key had
“comported himself well in prison.” App’x 412, 417. At the same time, the district
court acknowledged “the extraordinarily brutal and serious series of crimes
committed by Mr. Key over an extended period of time.” Id. at 412. It noted that
“given all of the factors in 3553(a) which I have considered here, the sentence will
be very substantial.” Id.; see also id. at 417 (“I have taken into account all of the
factors in [18 U.S.C. §] 3553(a) and I believe the sentence is appropriate given the
extraordinary seriousness of the offense and the need for punishment and
deterrence.”). We do not perceive an abuse of discretion in the resulting sentence.
Key’s arguments to the contrary are unavailing. The Guidelines provided
for a sentence of life in prison following convictions for, among other things,
murder-for-hire conspiracies. In varying downward, the district court adequately
considered such factors as Key’s efforts toward rehabilitation in prison, the impact
that Key’s incarceration has on Key’s family, and the possibility of further
rehabilitation. Indeed, Key’s new sentence gives him the chance to leave prison
during his life—a material change from Key’s original sentence. Key’s receiving a
higher sentence than did his codefendants was not surprising because Key was the
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mastermind and leader of the operation in question. 1 We reject Key’s substantive
unreasonableness challenge.
B
“A district court commits procedural error where,” as relevant here, it
“makes a mistake in its Guidelines calculation.” United States v. Cavera, 550 F.3d
180, 190 (2d Cir. 2008). Key did not object to the Guidelines calculation at the
resentencing, and “issues not raised in the trial court because of oversight,
including sentencing issues, are normally deemed forfeited on appeal unless they
meet our standard for plain error.” United States v. Villafuerte, 502 F.3d 204, 207 (2d
Cir. 2007). The plain-error test proceeds in four parts: “(1) there must be an error;
(2) the error must be plain, meaning it must be clear or obvious, rather than subject
to reasonable dispute; (3) the error must have affected the appellant’s substantial
rights in that it affected the outcome of the proceedings; and (4) if these other three
prongs are satisfied, the court of appeals has the discretion to remedy the error if
the error seriously affects the fairness, integrity or public reputation of judicial
proceedings.” United States v. Montague, 67 F.4th 520, 528 (2d Cir. 2023) (internal
quotation marks and alteration omitted).
In a supplemental brief that he filed pro se, Key contends that his sentence
is procedurally unreasonable. “[W]e liberally construe pleadings and briefs
submitted by pro se litigants, reading such submissions to raise the strongest
arguments they suggest.” McLeod v. Jewish Guild for the Blind, 864 F.3d 154, 156 (2d
Cir. 2017) (quoting Bertin v. United States, 478 F.3d 489, 491 (2d Cir. 2007)). We
construe Key’s supplemental brief to be arguing that the district court erred under
1 Key also suggests that his sentence created an unwarranted disparity with that imposed
on a defendant in an arguably similar case. In that case, however, the defendant did not
commit murder-for-hire or conspire to do so. See App’x 307-08 (referencing Transcript,
United States v. James, No. 13-CR-836-1 (S.D.N.Y. Dec. 6, 2019), ECF No. 364 (imposing a
132-month sentence for a one-count guilty plea to robbery conspiracy)); see also
Sentencing Submission, United States v. James, No. 13-CR-836-1 (S.D.N.Y. Oct. 10, 2019),
ECF No. 341 (describing the procedural background).
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U.S.S.G. § 5G1.2(c) when—at the resentencing—it modified Key’s existing
concurrent sentences to run consecutively. In Key’s telling, “the district court was
required to run [the sentences for] counts three, four, and six concurrent with count
one at the resentencing.” Supplemental Pro Se Br. 10 (emphasis added). The
district court sentenced Key in the following manner:
On Count One: 20 years. On Count Two: Five years, to run
consecutive to Count One. Count Three: 10 years, to run concurrent
with Count Four but consecutive to Counts One and Two. On Count
Four: 10 years, to run concurrent with Count Three but consecutive to
Counts One and Two. On Count Six: 10 years, to run consecutive to
Counts One, Two, Three, and Four. So the total term is 45 years.
App’x 414.
The district court did not plainly err in imposing this sentence. “If the
sentence imposed on the count carrying the highest statutory maximum is
adequate to achieve the total punishment, then the sentences on all counts shall
run concurrently, except to the extent otherwise required by law.” U.S.S.G.
§ 5G1.2(c). Even assuming that § 5G1.2(c) applies to Key, who is a career offender, 2
we conclude that the district court did not plainly err in structuring Key’s sentence
as it did. The district court varied downward from the Guidelines
recommendation of life imprisonment plus five years, determining that forty-five
years was a proper sentence. In other words, the district court determined that
forty-five years was the sentence “adequate to achieve the total punishment” and
that the twenty years on Count One, by itself, would be inadequate. U.S.S.G.
§ 5G1.2(c). For that reason, the district court did not contravene § 5G1.2(c). Even if
the district court had erred in imposing consecutive sentences, moreover, it still
could have imposed a sentence of forty-five years. Accordingly, “[t]he correct
aggregate sentence would thus have been a prison term identical to the sentence
2 For such offenders, U.S.S.G. § 5G1.2(e) is the applicable provision of the Guidelines.
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that was in fact imposed” and, “[i]n these circumstances, we cannot conclude that
the error affected [Key’s] substantial rights.” United States v. Blount, 291 F.3d 201,
214 (2d Cir. 2002). We reject Key’s procedural unreasonableness challenge.
II
“Because criminal forfeiture is viewed as part of the sentencing process, the
government need prove facts supporting forfeiture only by a preponderance of the
evidence.” United States v. Gaskin, 364 F.3d 438, 461 (2d Cir. 2004) (citation
omitted). “The calculation of forfeiture amounts is not an exact science.” United
States v. Treacy, 639 F.3d 32, 48 (2d Cir. 2011) “[T]he court ‘need not establish the
loss with precision but rather need only make a reasonable estimate of the loss,
given the available information.’” United States v. Uddin, 551 F.3d 176, 180 (2d Cir.
2009) (quoting United States v. Carboni, 204 F.3d 39, 46 (2d Cir. 2000)).
Key’s final argument is that the district court erred in ordering forfeiture.
He makes three points. First, Key contends that ordering forfeiture was
inappropriate at the resentencing. Second, he claims that the inclusion of a
forfeiture order in his new sentence violated his due process rights because it
constituted a more severe sentence than the one originally imposed. Third, he
argues that the district court did not properly determine the amount of forfeiture.
We disagree and address each point in turn.
First, the district court was entitled to order forfeiture at Key’s resentencing.
Key asked for—and received—a de novo resentencing. The government’s waiver
of its right to seek forfeiture at the initial sentencing did not preclude the
government from requesting it—or the district court from ordering it—at the
resentencing, given that the de novo proceeding permitted the district court to start
anew. Nor did forfeiture fall outside of the scope of the mandate from this court
to resentence Key. See United States v. Quintieri, 306 F.3d 1217, 1228 (2d Cir. 2002)
(“[R]esentencing usually should be de novo when a Court of Appeals reverses one
or more convictions and remands for resentencing.”) (emphasis omitted).
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Second, we disagree with Key’s contention that his sentence violates his due
process rights. The Supreme Court has explained that “[d]ue process of law …
requires that vindictiveness against a defendant for having successfully attacked
his first conviction must play no part in the sentence he receives after a new trial.”
North Carolina v. Pearce, 395 U.S. 711, 725 (1969). For that reason, the Court has
concluded that “[i]n order to assure the absence of [a retaliatory motivation on the
part of the sentencing judge], … whenever a judge imposes a more severe sentence
upon a defendant after a new trial, the reasons for his doing so must affirmatively
appear.” Id. at 725-26. Even assuming that a total sentence of forty-five years’
imprisonment and $16.2 million is more severe than Key’s original sentence of life
imprisonment plus thirty years—which we doubt—we conclude that the reasons
for ordering forfeiture “affirmatively appear.” The district court determined that
Key—who masterminded a drug trafficking organization and profited from his
illicit activities—obtained $16.2 million in “proceeds traceable to the [narcotics
offense] that … cannot be located upon the exercise of due diligence.” App’x 388.
Forfeiture was therefore appropriate.
Third, the district court properly determined the amount of the forfeiture.
The district court adopted the findings of fact in the presentence report and
ordered forfeiture in the amount of $16.2 million. That number reflects a
reasonable estimate of the drug proceeds based on testimony at the trial and
information discussed in the report. Key lodged a general objection to the facts
underlying this calculation but offered no reason to doubt those facts. We conclude
that the district court’s forfeiture order was reasonable.
* * *
We have considered Key’s remaining arguments, which we conclude are
without merit. For the foregoing reasons, we affirm the judgment of the district
court.
FOR THE COURT:
Catherine O’Hagan Wolfe, Clerk of Court
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