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Analysis: Lee v. U.S.

Kay L. Levine |

On June 23, 2017, the U.S. Supreme Court once again applied the Sixth Amendment ineffective assistance of counsel doctrine to attorney errors during plea negotiations. In Lee v. United States, a six-member majority led by Chief Justice Roberts found a Sixth Amendment violation where an attorney incorrectly advised a noncitizen defendant that guilty pleas do not trigger deportation, and the defendant established “by substantial and uncontroverted evidence” that he would not have pled guilty but for this advice.

Lee—a native of South Korea but a longtime resident of the United States—was charged with possession with intent to distribute ecstasy. At the time he was prosecuted, Lee had been living and working in Memphis for decades but had never applied for U.S. citizenship. His primary job was as a restauranteur; his hobby was, unfortunately, sharing ecstasy with his friends. He pled guilty on the advice of counsel, accepting counsel’s representation that he would not be deported. [This representation was patently incorrect, as possession with intent to distribute ecstasy is considered an aggravated felony that subjects the offender to automatic deportation after conviction by plea or by trial.] As soon as he learned he was about to be deported, Lee sought to vacate his conviction and sentence under 28 U.S.C. section 2255, alleging ineffectiveness of counsel. While a U.S. magistrate judge originally ruled in his favor, he lost at the District Court and again at the Sixth Circuit.

Lee’s case is the direct progeny of Padilla v. Kentucky, decided in 2010. Padilla was the first opinion in which the Supreme Court addressed how ineffectiveness on the issue of immigration consequences can potentially invalidate a conviction and sentence based on a guilty plea. The Padilla court held that defense counsel’s failure to advise of immigration consequences before a guilty plea amounts to error under Strickland v. Washington (1984) and Hill v. Lockhart (1985), because it falls outside the bounds of what a reasonable attorney would do. However, in order to get habeas relief, a defendant still has to convince the reviewing court that counsel’s error prejudiced him. In other words, he must show that his decision to plead guilty hinged on his mistake about deportability, and that it would have been rational for him to reject the plea deal on the basis of immigration consequences.

But if a defendant faces strong evidence of his guilt and very little chance of winning at trial, would it ever be rational for him to reject the government’s offer of reduced incarceration time in the hopes of staying in the country? The majority in Lee said yes, that the almost certainty of getting deported after trial was better than the absolute certainty of getting deported after a guilty plea. For that reason, a lower court facing an ineffectiveness challenge ought to consider the defendant’s own decision-making calculus, rather than imposing its preferences on the defendant. Considering respective connections to both countries in terms of length of residence, family, friends, business, and language ability, a defendant such as Lee might fear deportation (especially permanent deportation) more than a prison term of any length—deportation would be the “determinative issue.” And a defendant for whom deportation is the determinative issue might rationally reject any plea offer that imposes mandatory deportation, to keep negotiating for a nondeportable offense or to take his chances at trial. For a defendant in that circumstance, counsel’s error about the impossibility of deportation could sway the decision to plead guilty, even in the face of strong evidence of guilt.

Kay L. Levine, professor of law