United States v. Kerry Newman, 420 U.S. App. D.C. 89

Kerry Newman, a Jamaican national and lawful permanent resident since 1980, pleaded guilty in 2001 to one count of federal wire fraud arising from a real-estate flipping scheme.
Defense counsel never advised Newman that a guilty plea could carry immigration consequences; at sentencing counsel misstated immigration law, telling the court and Newman that deportation risk depended on the length of the sentence rather than the nature of the offense.
The district court relied on counsel’s incorrect advice and imposed a sentence it believed would be "beneficial" for immigration purposes.
In 2007 immigration authorities charged Newman as inadmissible based on his wire-fraud conviction (crime involving moral turpitude and an aggravated felony based on loss amount); Newman was removed to Jamaica after consenting to deportation on counsel of immigration counsel.
After Padilla v. Kentucky (2010) issued, Newman sought coram nobis relief arguing his trial counsel was ineffective for failing to advise and for providing affirmative misadvice about immigration consequences; the district court denied relief, concluding Newman could not show prejudice because the misadvice occurred after his plea.
The D.C. Circuit reverses and remands, holding the district court erred to deny coram nobis relief solely because the misadvice came after the plea and directing the district court to evaluate prejudice (whether Newman would have sought to withdraw his plea and obtained a different outcome).

Issue	Plaintiff's Argument	Defendant's Argument	Held
Whether counsel was ineffective for failing to research or consider immigration consequences when negotiating the plea	Newman: counsel had duty to investigate and mitigate immigration consequences during plea bargaining	Government: pre-Padilla counsel had no duty to advise; cannot be faulted for failing to research	Rejected: Padilla/Chaidez foreclose imposing such a pre-Padilla duty; district court properly denied this claim
Whether counsel's affirmative misrepresentation about immigration consequences (given pre- and at-sentencing) constituted ineffective assistance and whether Newman showed prejudice	Newman: affirmative misadvice was constitutionally deficient and could have caused him to refrain from withdrawing his plea or seek a different plea	Government: Newman cannot show prejudice because misrepresentations occurred after he pled guilty (too late to change result)	Reversed and remanded: timing alone does not foreclose prejudice; district court must decide on remand whether Newman can show a reasonable probability he would have withdrawn his plea and obtained a different outcome

Padilla v. Kentucky, 559 U.S. 356 (failure to advise on deportation consequences can be ineffective assistance)
Chaidez v. United States, 133 S. Ct. 1103 (Padilla announced a new rule; only convictions not yet final at Padilla benefit)
Strickland v. Washington, 466 U.S. 668 (standard for ineffective assistance: deficient performance and prejudice)
Hill v. Lockhart, 474 U.S. 52 (prejudice standard for guilty-plea challenges)
Missouri v. Frye, 132 S. Ct. 1399 (plea-bargain ineffective-assistance principles)
Morgan v. United States, 346 U.S. 502 (coram nobis as remedy for fundamental errors when not in custody)
Denedo v. United States, 556 U.S. 904 (coram nobis can redress Sixth Amendment errors)
Koon v. United States, 518 U.S. 81 (legal error justifies reversal)