Jae Lee, a South Korean national who had lived lawfully in the United States since his youth and operated a Memphis restaurant, was charged in federal court with possession of ecstasy with intent to distribute, a violation of 21 U.S.C. § 841(a)(1). Concerned about immigration consequences, Lee repeatedly asked his retained counsel whether pleading guilty would lead to his deportation. Counsel—mistakenly believing a plea would not trigger removal—assured Lee that he would not be deported if he accepted the plea. Relying on this advice, Lee pleaded guilty pursuant to an agreement under which the Government recommended a sentence of one year and one day. During the Rule 11 plea colloquy, the district judge issued a generic warning that a conviction could result in deportation; Lee and his lawyer continued to rely on counsel's affirmative assurances that deportation would not occur. After sentencing, Lee learned that his § 841 drug-trafficking conviction rendered him an aggravated felon subject to mandatory deportation. He moved under 28 U.S.C. § 2255 to vacate his plea, alleging ineffective assistance of counsel in violation of the Sixth Amendment. The district court found deficient performance under Padilla v. Kentucky and credited Lee's testimony that he would have gone to trial if properly advised, but denied relief on the ground that Lee could not show prejudice because the evidence of guilt was overwhelming. The Sixth Circuit affirmed. The Supreme Court granted certiorari.
Whether a defendant who received deficient advice that a guilty plea would not result in deportation can establish Strickland prejudice by showing a reasonable probability that, but for the misadvice, he would have rejected the plea and insisted on trial, even though conviction at trial was likely.
Under Strickland v. Washington and its plea-bargain application in Hill v. Lockhart, a defendant claiming ineffective assistance must show (1) deficient performance and (2) prejudice. In the plea context, prejudice requires a reasonable probability that, but for counsel's errors, the defendant would not have pleaded guilty and would have insisted on going to trial. The analysis focuses on the defendant's decisionmaking and whether rejecting the plea would have been rational under the circumstances, considering the totality of consequences—including, when the law is clear, mandatory deportation recognized in Padilla v. Kentucky. Generic plea colloquy warnings do not automatically cure counsel's affirmative misadvice.
Yes. Lee demonstrated prejudice under Strickland/Hill. Given the undisputed evidence that avoiding deportation was paramount and that he would have gone to trial had he known deportation was mandatory, it was rational for him to reject the plea notwithstanding the likelihood of conviction. The Supreme Court reversed the Sixth Circuit and remanded.
The Court emphasized that the prejudice inquiry in the plea context asks whether there is a reasonable probability the defendant would have made a different decision—not whether the defendant would probably have been acquitted at trial. While likely trial outcomes and sentencing exposure are relevant, courts must assess the defendant's priorities and the rationality of rejecting a plea in light of all material consequences. Deportation, the Court noted, is a particularly severe penalty tantamount to "banishment," and thus a defendant may rationally risk a trial—even one he is likely to lose—if the alternative is certain removal from the country. Here, both sides conceded deficient performance under Padilla because the immigration consequence of a § 841 drug-trafficking plea was clear: mandatory deportation as an aggravated felony. The record convincingly showed that Lee consistently prioritized avoiding deportation, repeatedly asked counsel about it, had lived in the United States since childhood, and had minimal ties to South Korea. The government's argument that overwhelming evidence of guilt defeats prejudice misapprehended the standard; a small chance of acquittal, a hung jury, or even the possibility of negotiating a different charge that might carry lesser immigration consequences can render the decision to proceed to trial rational when deportation is certain upon a plea. The Court also rejected the notion that the district court's generic admonition during the plea colloquy cured counsel's affirmative misadvice. The judge's statement that Lee "could" be deported did not correct counsel's repeated and confident assurances that he "would not" be deported, especially where the legal consequence was mandatory. Accordingly, Lee met Strickland's prejudice prong because, properly advised, he would have rejected the plea and insisted on trial.
Lee recalibrates the Strickland prejudice analysis in the plea-bargaining context by directing courts to evaluate the defendant's actual decision and priorities, not merely the likelihood of conviction. It confirms that severe collateral consequences—especially mandatory deportation—can make it rational to reject a favorable plea even in the face of strong evidence. For practitioners, Lee underscores the constitutional imperative to give accurate immigration advice and warns that boilerplate plea colloquies do not insulate convictions from post-conviction attacks based on affirmative misadvice. For students, Lee is essential to understanding the interplay among Strickland, Hill, and Padilla, and the centrality of client-centered counseling in plea negotiations.
Lee v. United States powerfully affirms that the Sixth Amendment protects a defendant's right to make informed, autonomous decisions about pleas in light of all material consequences, including mandatory deportation. By focusing the prejudice inquiry on the defendant's rational decisionmaking rather than purely on trial probabilities, the Court ensures that the Constitution safeguards choices that reflect a defendant's deepest stakes.