United States v. Gonzales, 884 F.3d 457

Gonzales, a lawful permanent resident, pleaded guilty in the W.D.N.Y. to drug- and firearm-related charges under a Rule 11(c)(1)(C) plea agreement calling for a 228-month sentence.
At the plea colloquy the district court did not inform Gonzales of the immigration consequences of conviction, as required by Fed. R. Crim. P. 11(b)(1)(O); the plea agreement and counsel also did not advise him.
The Presentence Report (PSR) later noted Gonzales "may be amenable to removal," and at sentencing Gonzales said he had been told not to worry about deportation.
The district court acknowledged Gonzales’s concern at sentencing but took no corrective action or further inquiry and proceeded to impose the agreed 228-month sentence and ordered delivery to immigration authorities after incarceration.
On appeal the government conceded the Rule 11 error; the Second Circuit reviewed whether the error was harmless and whether Gonzales’s substantial rights were affected.

Issue	Plaintiff's Argument	Defendant's Argument	Held
Whether the district court’s omission to advise an LPR of immigration consequences violated Rule 11	Gonzales: plea was not knowing/voluntary because he was not informed he would likely be removed	Government: error was harmless and would not have altered Gonzales’s decision to plead	Court: violation of Rule 11 occurred and was not harmless; vacated conviction and remanded
Whether the Rule 11 error affected Gonzales’s substantial rights (harmless-error standard)	Gonzales: likely would have considered deportation in plea decision given long residency and family ties	Government: benefit of plea and seriousness of charges show removal risk would not have changed decision	Court: government failed to show harmlessness; reasonable probability exists that the error affected decision-making
Whether sentencing-stage discussion cured the earlier Rule 11 omission	Gonzales: sentencing remarks show he was unaware at plea and raised concern promptly upon learning from PSR	Government: post-plea awareness or failure to immediately move to withdraw weakens claim	Court: sentencing-stage statements and court’s failure to follow up did not cure the Rule 11 defect
Whether vacatur/remand is required remedy	Gonzales: plea must be vacated and proceedings reopened	Government: uphold plea despite procedural lapse	Court: vacated judgment and remanded for further proceedings consistent with the opinion

Brady v. United States, 397 U.S. 742 (establishes standard that guilty plea must be knowing and voluntary)
United States v. Rossillo, 853 F.2d 1062 (2d Cir. 1988) (discusses Rule 11’s role in ensuring pleas are knowing and intelligent)
United States v. Pattee, 820 F.3d 496 (2d Cir. 2016) (requires strict adherence to Rule 11 and criticizes recurring noncompliance)
United States v. Davila, 569 U.S. 597 (harmless-error framework for Rule 11 violations)
United States v. Harrington, 354 F.3d 178 (2d Cir. 2003) (government bears burden to show misinformation did not affect defendant’s decision)
Padilla v. Kentucky, 559 U.S. 356 (deportation can be a particularly severe and determinative consequence of a plea)
Lee v. United States, 137 S. Ct. 1958 (deportation can be the determinative issue in plea decisions)
I.N.S. v. St. Cyr, 533 U.S. 289 (recognizes the centrality of immigration consequences to noncitizen plea decisions)