24-938 United States v. Simmons
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 27th day of March, two thousand twenty-five.
Present: SUSAN L. CARNEY, MICHAEL H. PARK, MARIA ARAÚJO KAHN, Circuit Judges. __________________________________________ UNITED STATES OF AMERICA,
Appellee,
v. 24-938(CON)
NAQUANN SIMMONS,
Defendant-Appellant. * __________________________________________
FOR DEFENDANT-APPELLANT: Devin McLaughlin, Langrock Sperry & Wool, LLP, Middlebury, VT.
FOR APPELLEE: Rebecca Rose Delfiner, Steven John Kochevar, for Damian Williams, United States Attorney for the Southern District of New York, New York, NY.
* The Clerk of Court is respectfully directed to amend the caption accordingly. Appeal from a judgment of the United States District Court for the Southern District of
New York (Engelmayer, J.).
UPON DUE CONSIDERATION, IT IS HEREBY ORDERED, ADJUDGED, AND
DECREED that the judgment of the district court is AFFIRMED.
Defendant-Appellant Naquann Simmons violated the terms of his supervised release by
traveling to Pennsylvania in an attempt to make an illegal purchase of two firearms. In March
2024, the district court revoked Simmons’s supervised release, sentenced him to 16 months’
imprisonment, and imposed a new term of 44 months of supervised release. Simmons now
challenges his sentence as procedurally and substantively unreasonable. We assume the parties’
familiarity with the underlying facts, the procedural history of the case, and the issues on appeal.
I. Procedural Reasonableness
“A sentence is procedurally unreasonable if the district court fails to calculate (or
improperly calculates) the Sentencing Guidelines range, treats the Sentencing Guidelines as
mandatory, fails to consider the § 3553(a) factors, selects a sentence based on clearly erroneous
facts, or fails adequately to explain the chosen sentence.” United States v. Smith, 949 F.3d 60,
66 (2d Cir. 2020) (quotation marks omitted). “Moreover, when a defendant fails to object to an
alleged sentencing error before the district court, we will ordinarily consider any later objections
forfeited on appeal unless the defendant can meet the plain-error standard.” United States v.
Davis, 82 F.4th 190, 196 (2d Cir. 2023). To show plain error, a defendant must establish that
“(1) there is an error; (2) the error is clear or obvious, rather than subject to reasonable dispute; (3)
the error affected the appellant’s substantial rights, which in the ordinary case means it affected
2 the outcome of the district court proceedings; and (4) the error seriously affects the fairness,
integrity or public reputation of judicial proceedings.” United States v. Marcus, 560 U.S. 258,
262 (2010) (alteration adopted and quotations omitted).
At sentencing, Simmons failed to object to the district court’s § 3553(a) analysis. He now
argues on appeal that his sentence is procedurally unreasonable because the district court
determined that Simmons was attempting to purchase a firearm for “a disqualified person” based
only on an “unproven recitation of facts,” and on that basis alone imposed its sentence.
Appellant’s Br. at 11. We disagree.
First, the district court relied on more than “pure allegation based on speculation.”
Appellant’s Br. at 10. As the district court detailed, Simmons “left New York State having
undertaken at least a degree of planning and lin[ed] up a straw purchaser.” App’x at 90. He
chose “a state in which gun purchases could be performed more easily.” Id. And according to
surveillance footage presented by the government, he made a FaceTime call from the gun store to
show someone one of the two guns he was attempting to purchase. See id. at 73. Based on that
information, the district court concluded that “[c]ircumstantially it appears that one of the guns
was destined for another person,” which “in turn suggests that that other person quite likely was
barred from gun possession.” Id. at 90. In sentencing, a district court “may base its factfinding
on circumstantial evidence and on reasonable inferences drawn therefrom.” United States v.
Gaskin, 364 F.3d 438, 464 (2d Cir. 2004). So we see no procedural error—let alone plain error—
in the district court’s analysis.
Second, the district court identified “a number of factors that point[ed] towards a lengthy
sentence.” App’x at 89. It highlighted the fact that it is “relatively rare” for a defendant to
3 violate supervised release in a manner that “endangers the public.” Id. It underscored that the
offense “tracks to some degree the underlying conduct” for which Simmons had originally been
sentenced. Id. at 90. And it emphasized its view that to deter Simmons from future illegal
conduct, “the federal criminal system of justice has to respond in a strong fashion here to get the
message across.” Id. at 91. The district court thus had ample reasons for imposing its sentence.
II. Substantive Reasonableness
“We review the substantive reasonableness of a district court’s sentence under a deferential
abuse-of-discretion standard.” United States v. Gates, 84 F.4th 496, 504-05 (2d Cir. 2023)
(quotation marks omitted). “A sentence is substantively unreasonable when it cannot be located
within the range of permissible decisions, because it is shockingly high, shockingly low, or
otherwise unsupportable as a matter of law.” United States v. Osuba, 67 F.4th 56, 68 (2d Cir.
2023) (quotation marks omitted). We “vacate a sentence for substantive unreasonableness only
in exceptional cases.” Davis, 82 F.4th at 200 (quotation marks omitted).
Simmons argues that his conduct “does not warrant a sentence that goes above the
Guidelines.” Appellant’s Br. at 14. But the district court went “above the top of the guideline
range” to “reflect the extent of the abuse of trust here, the need to protect the public,” and “the
need for the sentence to serve as a deterrent.” App’x at 93. As the district court explained, the
conduct at issue was “egregious” and “far, far more significant” than “most violations of
supervised release.” Id. at 90. Simmons tried “buying two dangerous guns across state lines,
using a straw purchaser.” Id. at 94. Still, the district court considered “mitigating” factors,
including the fact that Simmons “pled guilty” and is a “loving father,” and noted that “the sentence
would have been at least a couple of months higher” otherwise. Id. at 92.
4 Simmons further argues that his sentence is substantively unreasonable because the district
court gave “so much weight to th[e] unproven evidence” that Simmons was purchasing a firearm
for a prohibited person. Appellant’s Br. at 14.
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24-938 United States v. Simmons
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 27th day of March, two thousand twenty-five.
Present: SUSAN L. CARNEY, MICHAEL H. PARK, MARIA ARAÚJO KAHN, Circuit Judges. __________________________________________ UNITED STATES OF AMERICA,
Appellee,
v. 24-938(CON)
NAQUANN SIMMONS,
Defendant-Appellant. * __________________________________________
FOR DEFENDANT-APPELLANT: Devin McLaughlin, Langrock Sperry & Wool, LLP, Middlebury, VT.
FOR APPELLEE: Rebecca Rose Delfiner, Steven John Kochevar, for Damian Williams, United States Attorney for the Southern District of New York, New York, NY.
* The Clerk of Court is respectfully directed to amend the caption accordingly. Appeal from a judgment of the United States District Court for the Southern District of
New York (Engelmayer, J.).
UPON DUE CONSIDERATION, IT IS HEREBY ORDERED, ADJUDGED, AND
DECREED that the judgment of the district court is AFFIRMED.
Defendant-Appellant Naquann Simmons violated the terms of his supervised release by
traveling to Pennsylvania in an attempt to make an illegal purchase of two firearms. In March
2024, the district court revoked Simmons’s supervised release, sentenced him to 16 months’
imprisonment, and imposed a new term of 44 months of supervised release. Simmons now
challenges his sentence as procedurally and substantively unreasonable. We assume the parties’
familiarity with the underlying facts, the procedural history of the case, and the issues on appeal.
I. Procedural Reasonableness
“A sentence is procedurally unreasonable if the district court fails to calculate (or
improperly calculates) the Sentencing Guidelines range, treats the Sentencing Guidelines as
mandatory, fails to consider the § 3553(a) factors, selects a sentence based on clearly erroneous
facts, or fails adequately to explain the chosen sentence.” United States v. Smith, 949 F.3d 60,
66 (2d Cir. 2020) (quotation marks omitted). “Moreover, when a defendant fails to object to an
alleged sentencing error before the district court, we will ordinarily consider any later objections
forfeited on appeal unless the defendant can meet the plain-error standard.” United States v.
Davis, 82 F.4th 190, 196 (2d Cir. 2023). To show plain error, a defendant must establish that
“(1) there is an error; (2) the error is clear or obvious, rather than subject to reasonable dispute; (3)
the error affected the appellant’s substantial rights, which in the ordinary case means it affected
2 the outcome of the district court proceedings; and (4) the error seriously affects the fairness,
integrity or public reputation of judicial proceedings.” United States v. Marcus, 560 U.S. 258,
262 (2010) (alteration adopted and quotations omitted).
At sentencing, Simmons failed to object to the district court’s § 3553(a) analysis. He now
argues on appeal that his sentence is procedurally unreasonable because the district court
determined that Simmons was attempting to purchase a firearm for “a disqualified person” based
only on an “unproven recitation of facts,” and on that basis alone imposed its sentence.
Appellant’s Br. at 11. We disagree.
First, the district court relied on more than “pure allegation based on speculation.”
Appellant’s Br. at 10. As the district court detailed, Simmons “left New York State having
undertaken at least a degree of planning and lin[ed] up a straw purchaser.” App’x at 90. He
chose “a state in which gun purchases could be performed more easily.” Id. And according to
surveillance footage presented by the government, he made a FaceTime call from the gun store to
show someone one of the two guns he was attempting to purchase. See id. at 73. Based on that
information, the district court concluded that “[c]ircumstantially it appears that one of the guns
was destined for another person,” which “in turn suggests that that other person quite likely was
barred from gun possession.” Id. at 90. In sentencing, a district court “may base its factfinding
on circumstantial evidence and on reasonable inferences drawn therefrom.” United States v.
Gaskin, 364 F.3d 438, 464 (2d Cir. 2004). So we see no procedural error—let alone plain error—
in the district court’s analysis.
Second, the district court identified “a number of factors that point[ed] towards a lengthy
sentence.” App’x at 89. It highlighted the fact that it is “relatively rare” for a defendant to
3 violate supervised release in a manner that “endangers the public.” Id. It underscored that the
offense “tracks to some degree the underlying conduct” for which Simmons had originally been
sentenced. Id. at 90. And it emphasized its view that to deter Simmons from future illegal
conduct, “the federal criminal system of justice has to respond in a strong fashion here to get the
message across.” Id. at 91. The district court thus had ample reasons for imposing its sentence.
II. Substantive Reasonableness
“We review the substantive reasonableness of a district court’s sentence under a deferential
abuse-of-discretion standard.” United States v. Gates, 84 F.4th 496, 504-05 (2d Cir. 2023)
(quotation marks omitted). “A sentence is substantively unreasonable when it cannot be located
within the range of permissible decisions, because it is shockingly high, shockingly low, or
otherwise unsupportable as a matter of law.” United States v. Osuba, 67 F.4th 56, 68 (2d Cir.
2023) (quotation marks omitted). We “vacate a sentence for substantive unreasonableness only
in exceptional cases.” Davis, 82 F.4th at 200 (quotation marks omitted).
Simmons argues that his conduct “does not warrant a sentence that goes above the
Guidelines.” Appellant’s Br. at 14. But the district court went “above the top of the guideline
range” to “reflect the extent of the abuse of trust here, the need to protect the public,” and “the
need for the sentence to serve as a deterrent.” App’x at 93. As the district court explained, the
conduct at issue was “egregious” and “far, far more significant” than “most violations of
supervised release.” Id. at 90. Simmons tried “buying two dangerous guns across state lines,
using a straw purchaser.” Id. at 94. Still, the district court considered “mitigating” factors,
including the fact that Simmons “pled guilty” and is a “loving father,” and noted that “the sentence
would have been at least a couple of months higher” otherwise. Id. at 92.
4 Simmons further argues that his sentence is substantively unreasonable because the district
court gave “so much weight to th[e] unproven evidence” that Simmons was purchasing a firearm
for a prohibited person. Appellant’s Br. at 14. But the district court made clear that its
“overwhelming focus” was the “abuse of trust reflected in the violations of supervised release.”
App’x at 88. It emphasized that the fact that Simmons attempted to purchase firearms as a
“convicted felon” was itself “alarming conduct.” Id. at 89-90. And it explained that regardless
of whether Simmons was procuring the gun for someone else, purchasing the gun “could only have
resulted in bad things happening,” especially given that “[g]un violence in this district is out of
control.” Id. at 91. Given the district court’s “very wide latitude to decide the proper degree of
punishment,” we find no abuse of discretion in the sentence. United States v. DiMassa, 117 F.4th
477, 482 (2d Cir. 2024) (quotation marks omitted).
* * *
We have considered Simmons’s remaining arguments and find them to be without merit.
For the foregoing reasons, the judgment of the district court is AFFIRMED.
FOR THE COURT: Catherine O’Hagan Wolfe, Clerk of Court