22-1400

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. 

1 At a stated term of the United States Court of Appeals for the Second Circuit, 

2 held at the Thurgood Marshall United States Courthouse, 40 Foley Square, in the City of 

New York, on the 12th 3 day of January, two thousand twenty-four.

4

5 PRESENT:

6 MICHAEL H. PARK,

7 EUNICE C. LEE,

8 SARAH A. L. MERRIAM,

9 Circuit Judges.

10 _____________________________________

11

12 United States of America,

13

14 Appellee,

15

16 v. 22-1400

17

18 Devan A. Simmons,

19

20 Defendant-Appellant.

21 _____________________________________

22

23 FOR APPELLEE: TIFFANY H. LEE (Monica J. Richards, on the brief), 

24 Assistant United States Attorneys, for Trini E. Ross, 

25 United States Attorney for the Western District of 

26 New York, Buffalo, NY.

27

28 FOR DEFENDANT-APPELLANT: JEREMIAH DONOVAN, Law Offices of Jeremiah 

29 Donovan, Old Saybrook, CT. 

30
2

1 Appeal from a judgment of the United States District Court for the Western District of New 

2 York (Siragusa, J.).

3 UPON DUE CONSIDERATION, IT IS HEREBY ORDERED, ADJUDGED, AND 

4 DECREED that the appeal is DISMISSED.

5 Devan Simmons pleaded guilty to possession with intent to distribute, and distribution of, 

6 fentanyl. As part of his plea agreement, which included an appeal waiver, the parties agreed that 

7 the appropriate sentencing range would be 84 to 105 months of imprisonment. At sentencing, the 

8 district court accepted the Rule 11(c)(1)(C) plea agreement and imposed a sentence, as relevant 

9 here, of 105 months of imprisonment and three years of supervised release. Simmons now

10 appeals, arguing the district court’s sentence was substantively unreasonable because 84 months 

11 would have been enough to deter future crimes. In seeking review of his sentence, Simmons asks 

12 this Court not to enforce the appeal waiver included in his plea agreement because he contends 

13 that the waiver was not made knowingly or voluntarily. We assume the parties’ familiarity with 

14 the facts, the procedural posture, and the issues on appeal.

15 “[W]aivers of the right to appeal a sentence are presumptively enforceable.” United States 

16 v. Burden, 860 F.3d 45, 51 (2d Cir. 2017) (quoting United States v. Arevalo, 628 F.3d 93, 98 (2d 

17 Cir. 2010)). “In some cases, a defendant may have a valid claim that the waiver of appellate rights 

18 is unenforceable, such as when the waiver was not made knowingly, voluntarily, and 

19 competently.” United States v. Gomez-Perez, 215 F.3d 315, 319 (2d Cir. 2000). When a 

20 defendant fails to object to a Rule 11 violation, we review for plain error under Fed. R. Crim. P. 

21 52(b). United States v. Vaval, 404 F.3d 144, 151 (2d Cir. 2005). “Plain error review requires a 
3

1 defendant to demonstrate that (1) there was error, (2) the error was plain, (3) the error prejudicially 

2 affected his substantial rights, and (4) the error seriously affected the fairness, integrity or public 

3 reputation of judicial proceedings. . . . Additionally, to show that a Rule 11 violation was plain 

4 error, the defendant must demonstrate that there is a reasonable probability that, but for the error, 

5 he would not have entered the plea.” United States v. Cook, 722 F.3d 477, 481 (2d Cir. 2013)

6 (quoting United States v. Youngs, 687 F.3d 56, 59 (2d Cir. 2012)).

7 Simmons’s challenge to the substantive reasonableness of his sentence is barred by his 

8 appeal waiver. The district court did not commit plain error when discussing the appeal waiver 

9 with Simmons at the plea hearing. Simmons confirmed that he understood the plea agreement, 

10 that he discussed it with counsel, that he had all his questions answered by counsel, and that he 

11 knowingly and voluntarily agreed to it. The district court reminded Simmons multiple times to 

12 stop the proceeding if he had any remaining questions about the plea agreement, and Simmons did 

13 not do so. The plea agreement informs Simmons that, by entering into it, he “knowingly waives 

14 the right to appeal and collaterally attack any component of a sentence imposed by the Court which 

15 falls within or is less than the sentencing range for imprisonment, a fine and supervised release set 

forth . . . above.” App’x at A-32.1 16

17 Simmons argues that the plea colloquy around the waiver was difficult for a layperson to 

18 follow, but even assuming that to be true, he cannot establish plain error. First, as noted above, 

19 the record demonstrates that Simmons understood and agreed to the terms of the plea agreement. 

1 To be sure, the written plea agreement could have been clearer by stating explicitly that Simmons 

waived his right to appeal a sentence of 188 months of imprisonment or less, rather than referencing the 

government’s (contested) calculation of the Guidelines, which led to the colloquy discussed below. See

App’x at A-32. 
4

1 Second, in any event, Simmons cannot show “a reasonable probability that, but for the error, he 

2 would not have entered the plea.” Cook, 722 F.3d at 481 (quoting Youngs, 687 F.3d at 59). In 

3 fact, he seeks to keep the plea agreement in place but to be resentenced to the low end of the agreed 

4 to sentencing range of 84 months. Because he seeks to retain the benefit of the plea agreement, 

5 Simmons fails to show that he would not have agreed to the appeal waiver absent the newly alleged 

6 confusion. His waiver was made knowingly and voluntarily, and is thus enforceable. 

7 We have considered all of Simmons’s remaining arguments and find them to be without 

8 merit. For the foregoing reasons, Simmons’s appeal is DISMISSED as barred by his appeal 

9 waiver. 

10

11 FOR THE COURT: 

12 Catherine O’Hagan Wolfe, Clerk of Court