19-575 United States v. Prettyman
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 TO 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 3 New York, on the 29th day of October, two thousand twenty-one. 4 5 PRESENT: 6 JON O. NEWMAN, 7 GERARD E. LYNCH, 8 MICHAEL H. PARK, 9 Circuit Judges. 10 _____________________________________ 11 12 UNITED STATES OF AMERICA, 13 14 Appellee, 15 16 v. 19-575-cr 17 18 ANTHONY J. PRETTYMAN, 19 20 Defendant-Appellant. 21 _____________________________________ 22 23 FOR PLAINTIFF-APPELLANT: Malvina Nathanson, New York, NY. 24 25 FOR APPELLEE: Monica J. Richards for James P. Kennedy, 26 Jr., United States Attorney for the Western 27 District of New York, Buffalo, NY. 28 1 Appeal from a judgment of the United States District Court for the Western District of New
2 York (Geraci, J.).
3 UPON DUE CONSIDERATION, IT IS HEREBY ORDERED, ADJUDGED, AND
4 DECREED that the March 5, 2019 judgment of the district court is AFFIRMED.
5 In October 2016, Anthony J. Prettyman was arrested for transporting furanyl fentanyl. He
6 pled guilty to conspiracy to possess with intent to distribute, and to distribute, 100 grams or more
7 of furanyl fentanyl in violation of 21 U.S.C. §§ 841(a)(1), (b)(1)(A), and 846. Throughout his
8 pretrial hearings, Prettyman expressed some confusion and explained that he had difficulty
9 obtaining medications for his mental-health issues. At his change-of-plea hearing, Prettyman
10 informed the court that he was taking hydroxyzine and lithium but he assured the court that he did
11 not believe they were affecting his ability to understand the proceeding. When the court questioned
12 Prettyman to ensure that there was a factual basis for his plea, Prettyman answered evasively, and
13 defense counsel repeatedly tried to clarify Prettyman’s answers to the court. At one point, the
14 court directed defense counsel to have a discussion with Prettyman off the record to determine if
15 he was ready to enter a guilty plea. Back on the record, Prettyman answered questions with “yes”
16 and “no” and did not express any further misunderstandings.
17 Prettyman argues that we should vacate his conviction for two reasons. First, he asserts
18 that the district court abused its discretion by failing to order a competency examination sua sponte
19 pursuant to 18 U.S.C. § 4241(a). Second, he contends that the district court did not follow the
20 requirements of Federal Rule of Criminal Procedure 11 to ensure that his guilty plea was knowing
21 and voluntary because the court failed to inquire about the side effects of his medications before
22 accepting his plea. We assume the parties’ familiarity with the underlying facts, procedural
23 history, and issues on appeal.
2 1 I. Competency Hearing
2 We review a district court’s determination not to order a competency hearing sua sponte
3 for abuse of discretion. United States v. Quintieri, 306 F.3d 1217, 1232–33 (2d Cir. 2002). The
4 Fourteenth Amendment’s Due Process Clause “prohibits the criminal prosecution of a defendant
5 who is not competent to stand trial.” Id. at 1232 (citation omitted). A court shall order “a hearing
6 to determine the mental competency of the defendant” “if there is reasonable cause to believe that
7 the defendant may presently be suffering from a mental disease or defect rendering him mentally
8 incompetent to the extent that he is unable to understand the nature and consequences of the
9 proceedings against him or to assist properly in his defense.” 18 U.S.C. § 4241(a). This is a
10 “highly particularized assessment that varies in each case.” United States v. DiMartino, 949 F.3d
11 67, 71 (2d Cir. 2020) (internal quotation marks omitted). As such, “we afford district courts wide
12 latitude to reach conclusions as to both ‘reasonable cause’ and a criminal defendant’s overall
13 competence to stand trial.” United States v. Arenburg, 605 F.3d 164, 165 (2d Cir. 2010).
14 Here, the district court acted well within its discretion by deciding not to order a
15 competency hearing sua sponte before accepting Prettyman’s guilty plea. Prettyman argues that
16 the district court was obligated to order a competency hearing because it “was aware that [he] had
17 mental health problems, . . . that [he] was having difficulties in obtaining the correct medication, .
18 . . [that he] frequently expressed his confusion about what was going on, and [that he] interrupted
19 the plea-taking process by questioning many of the factual assertions that were the foundation of
20 his plea.” Appellant Br. 21. It is true that the district court was well aware of Prettyman’s mental-
21 health issues and repeatedly discussed them with Prettyman and his counsel. But as the district
22 noted, “[h]aving mental health conditions is not tantamount to a finding that somebody is not
23 competent to proceed.” App’x 87; see United States v. Vamos, 797 F.2d 1146, 1150 (2d Cir. 1986)
3 1 (“[S]ome degree of mental illness cannot be equated with incompetence to stand trial.”). And
2 Prettyman repeatedly assured the district court that he understood the explanations provided to him
3 during pretrial hearings and at the change-of-plea hearing. When he did not understand, he asked
4 for clarification, which the district court and his attorney provided. See, e.g., App’x 33 (“COURT:
5 Mr. Prettyman, do you understand what we’re talking about? PRETTYMAN: No.”, after which
6 the court sent Prettyman to discuss the matter with his counsel before proceeding); id. at 141–43
7 (district court explaining the difference between an information and an indictment after Prettyman
8 expressed confusion). Furthermore, when the district court brought up the possibility of a
9 competency hearing, Prettyman’s counsel repeatedly assured the court that his client did not need
10 one. See App’x 36 (after the district court brought up a mental competency examination,
11 Prettyman’s counsel assured the court, “[t]hat’s not what I’m asking [for]”); id. at 93 (Prettyman’s
12 counsel assured the district court that Prettyman is “doing better” with respect to “medical and
13 psychiatric issues”); id. at 100 (“PRETTYMAN’S COUNSEL: Your Honor, in regard to . . . that
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19-575 United States v. Prettyman
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 TO 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 3 New York, on the 29th day of October, two thousand twenty-one. 4 5 PRESENT: 6 JON O. NEWMAN, 7 GERARD E. LYNCH, 8 MICHAEL H. PARK, 9 Circuit Judges. 10 _____________________________________ 11 12 UNITED STATES OF AMERICA, 13 14 Appellee, 15 16 v. 19-575-cr 17 18 ANTHONY J. PRETTYMAN, 19 20 Defendant-Appellant. 21 _____________________________________ 22 23 FOR PLAINTIFF-APPELLANT: Malvina Nathanson, New York, NY. 24 25 FOR APPELLEE: Monica J. Richards for James P. Kennedy, 26 Jr., United States Attorney for the Western 27 District of New York, Buffalo, NY. 28 1 Appeal from a judgment of the United States District Court for the Western District of New
2 York (Geraci, J.).
3 UPON DUE CONSIDERATION, IT IS HEREBY ORDERED, ADJUDGED, AND
4 DECREED that the March 5, 2019 judgment of the district court is AFFIRMED.
5 In October 2016, Anthony J. Prettyman was arrested for transporting furanyl fentanyl. He
6 pled guilty to conspiracy to possess with intent to distribute, and to distribute, 100 grams or more
7 of furanyl fentanyl in violation of 21 U.S.C. §§ 841(a)(1), (b)(1)(A), and 846. Throughout his
8 pretrial hearings, Prettyman expressed some confusion and explained that he had difficulty
9 obtaining medications for his mental-health issues. At his change-of-plea hearing, Prettyman
10 informed the court that he was taking hydroxyzine and lithium but he assured the court that he did
11 not believe they were affecting his ability to understand the proceeding. When the court questioned
12 Prettyman to ensure that there was a factual basis for his plea, Prettyman answered evasively, and
13 defense counsel repeatedly tried to clarify Prettyman’s answers to the court. At one point, the
14 court directed defense counsel to have a discussion with Prettyman off the record to determine if
15 he was ready to enter a guilty plea. Back on the record, Prettyman answered questions with “yes”
16 and “no” and did not express any further misunderstandings.
17 Prettyman argues that we should vacate his conviction for two reasons. First, he asserts
18 that the district court abused its discretion by failing to order a competency examination sua sponte
19 pursuant to 18 U.S.C. § 4241(a). Second, he contends that the district court did not follow the
20 requirements of Federal Rule of Criminal Procedure 11 to ensure that his guilty plea was knowing
21 and voluntary because the court failed to inquire about the side effects of his medications before
22 accepting his plea. We assume the parties’ familiarity with the underlying facts, procedural
23 history, and issues on appeal.
2 1 I. Competency Hearing
2 We review a district court’s determination not to order a competency hearing sua sponte
3 for abuse of discretion. United States v. Quintieri, 306 F.3d 1217, 1232–33 (2d Cir. 2002). The
4 Fourteenth Amendment’s Due Process Clause “prohibits the criminal prosecution of a defendant
5 who is not competent to stand trial.” Id. at 1232 (citation omitted). A court shall order “a hearing
6 to determine the mental competency of the defendant” “if there is reasonable cause to believe that
7 the defendant may presently be suffering from a mental disease or defect rendering him mentally
8 incompetent to the extent that he is unable to understand the nature and consequences of the
9 proceedings against him or to assist properly in his defense.” 18 U.S.C. § 4241(a). This is a
10 “highly particularized assessment that varies in each case.” United States v. DiMartino, 949 F.3d
11 67, 71 (2d Cir. 2020) (internal quotation marks omitted). As such, “we afford district courts wide
12 latitude to reach conclusions as to both ‘reasonable cause’ and a criminal defendant’s overall
13 competence to stand trial.” United States v. Arenburg, 605 F.3d 164, 165 (2d Cir. 2010).
14 Here, the district court acted well within its discretion by deciding not to order a
15 competency hearing sua sponte before accepting Prettyman’s guilty plea. Prettyman argues that
16 the district court was obligated to order a competency hearing because it “was aware that [he] had
17 mental health problems, . . . that [he] was having difficulties in obtaining the correct medication, .
18 . . [that he] frequently expressed his confusion about what was going on, and [that he] interrupted
19 the plea-taking process by questioning many of the factual assertions that were the foundation of
20 his plea.” Appellant Br. 21. It is true that the district court was well aware of Prettyman’s mental-
21 health issues and repeatedly discussed them with Prettyman and his counsel. But as the district
22 noted, “[h]aving mental health conditions is not tantamount to a finding that somebody is not
23 competent to proceed.” App’x 87; see United States v. Vamos, 797 F.2d 1146, 1150 (2d Cir. 1986)
3 1 (“[S]ome degree of mental illness cannot be equated with incompetence to stand trial.”). And
2 Prettyman repeatedly assured the district court that he understood the explanations provided to him
3 during pretrial hearings and at the change-of-plea hearing. When he did not understand, he asked
4 for clarification, which the district court and his attorney provided. See, e.g., App’x 33 (“COURT:
5 Mr. Prettyman, do you understand what we’re talking about? PRETTYMAN: No.”, after which
6 the court sent Prettyman to discuss the matter with his counsel before proceeding); id. at 141–43
7 (district court explaining the difference between an information and an indictment after Prettyman
8 expressed confusion). Furthermore, when the district court brought up the possibility of a
9 competency hearing, Prettyman’s counsel repeatedly assured the court that his client did not need
10 one. See App’x 36 (after the district court brought up a mental competency examination,
11 Prettyman’s counsel assured the court, “[t]hat’s not what I’m asking [for]”); id. at 93 (Prettyman’s
12 counsel assured the district court that Prettyman is “doing better” with respect to “medical and
13 psychiatric issues”); id. at 100 (“PRETTYMAN’S COUNSEL: Your Honor, in regard to . . . that
14 one issue of mental competence, I would revoke or rescind my potential request. . . . [Prettyman]
15 appears to be much more stable or very stable in regard to the issues we discussed in the past.”);
16 id. at 110 (Prettyman’s counsel assured the court “[Prettyman] is in excellent shape”). Prettyman’s
17 counsel never indicated to the district court that Prettyman “had any difficulty assisting in
18 preparation or in comprehending the nature of the proceedings,” which provided “substantial
19 evidence of [Prettyman’s] competence.” Quintieri, 306 F.3d at 1233.
20 In short, Prettyman’s assurances of his own understanding, combined with repeated
21 assurances by his counsel leading up to the change-of-plea hearing that a competency hearing was
22 unnecessary, sufficiently dispelled any reasonable doubt about his competence. Under these
23 circumstances, the district court did not abuse its discretion by not ordering a competency hearing
4 1 sua sponte under 18 U.S.C. § 4241.
2 II. Rule 11
3 We review an alleged Federal Rule of Criminal Procedure 11 error raised for the first time
4 on appeal for plain error. See United States v. Vonn, 535 U.S. 55, 59 (2002); United States v. Yang
5 Chia Tien, 720 F.3d 464, 469 (2d Cir. 2013). Under plain error review, a defendant must
6 demonstrate “an error that is plain and that affects substantial rights.” United States v. Garcia,
7 587 F.3d 509, 515 (2d Cir. 2009) (cleaned up). The appellant “bears the burden of persuasion on
8 appeal to show that the district court committed plain error.” United States v. Gore, 154 F.3d 34,
9 42 (2d Cir. 1998). And even if a defendant can do so, “courts of appeals should only exercise their
10 discretion to correct the forfeited error . . . when the error seriously affects the fairness, integrity
11 or public reputation of judicial proceedings.” Garcia, 587 F.3d at 515 (internal quotation marks
12 omitted).
13 Prettyman has not satisfied his burden of persuasion. He faults the district court for failing
14 to “make any inquiry as to the possible effect that [his psychiatric] medication might have had on
15 his mental state.” Appellant Br. 32. Prettyman asserts that this failure, combined with his
16 difficulty receiving the correct medications and his lack of understanding during the change-of-
17 plea hearing, should have prompted the district court to inquire further whether his plea was
18 knowing and voluntary before accepting it. But the district court did ask whether Prettyman’s
19 medications affected his ability to understand, so even if it had committed an error by not
20 specifically asking about the medications’ side effects, the failure to do so would not have risen to
21 plain error. Moreover, Prettyman makes no argument that the error affected his substantial rights
22 or “seriously affected the fairness, integrity or public reputation of judicial proceedings.” See
23 Garcia, 587 F.3d at 515. Thus, we affirm Prettyman’s conviction on that basis.
5 1 * * *
2 We have considered the remainder of Prettyman’s arguments and find them to be without
3 merit. For the foregoing reasons, we affirm the judgment of the district court.
4 FOR THE COURT: 5 Catherine O’Hagan Wolfe, Clerk of Court