667 F. App'x 336
2d Cir.2016Background
- Defendant Ira Richards pleaded guilty before a magistrate judge in the Southern District of New York and was later sentenced; he appealed the conviction.
- At the plea colloquy the magistrate judge did not inform Richards that a guilty plea could result in deportation, as required by Federal Rule of Criminal Procedure 11(b)(1)(O).
- Richards argued the omission violated Rule 11 and his Fifth Amendment Due Process rights and sought vacatur of his plea.
- The presentence report (PSR) expressly stated immigration records indicated Richards was a permanent resident and that his conviction could lead to deportation; Richards and his counsel reviewed the PSR, and counsel relied on possible deportation in sentencing submissions.
- The Second Circuit agreed the Rule 11 omission was error but held Richards failed to demonstrate that the error prejudicially affected his substantial rights under plain-error review.
- The Court also noted a separate, unraised Rule 32 deficiency at sentencing (court did not verify counsel had discussed the PSR with the defendant) but declined relief because it was not preserved or pursued on appeal.
Issues
| Issue | Plaintiff's Argument | Defendant's Argument | Held |
|---|---|---|---|
| Whether omission of Rule 11(b)(1)(O) warning invalidates plea | The government argued any Rule 11 error was harmless because Richards knew or learned of deportation risk before sentencing | Richards argued the omitted warning violated Rule 11 and due process and warrants vacatur | Court: Error occurred but under plain-error review Richards cannot show a reasonable probability he would have refused the plea; affirm conviction |
| Whether defendant preserved challenge or must meet plain-error standard | Government: No timely objection below; plain-error applies | Richards: Invoked Rule 11 and due process on appeal; argued relief nonetheless warranted | Court: Applied plain-error standard (Vonn/Pattee); Richards failed third prong (prejudice) |
| Effect of learning omission before sentencing on withdrawal chance | Government: Learning before sentencing and failing to move to withdraw forecloses showing prejudice | Richards: Contended omission still undermined voluntariness | Court: Because PSR disclosed deportation risk and counsel relied on it, no reasonable probability he'd have withdrawn plea (citing Tulsiram) |
| Whether sentencing Rule 32 inquiry warranted reversal | Government: Not raised; harmless/unpreserved | Richards: Did not press this ground on appeal | Court: Identified district court’s inquiry was insufficient under Rule 32(i)(1)(A) but provided no relief because error not preserved/pressed on appeal |
Key Cases Cited
- United States v. Pattee, 820 F.3d 496 (2d Cir. 2016) (plain-error standard for unpreserved Rule 11 errors)
- United States v. Vonn, 535 U.S. 55 (U.S. 2002) (plain-error review for Rule 11 violations)
- United States v. Tulsiram, 815 F.3d 114 (2d Cir. 2016) (failure to move to withdraw plea after learning omitted Rule 11 info defeats prejudice showing)
- United States v. DeLeon, 704 F.3d 189 (1st Cir. 2013) (better practice for courts to verify defendant discussed PSR with counsel)