Here’s the Court’s Headnote (not part of the decision)
Petitioner Jae Lee moved to the United States from South Korea with his parents when he was 13. In the 35 years he has spent in this country, he has never returned to South Korea, nor has he become a U. S. citizen, living instead as a lawful permanent resident. In 2008, federal officials received a tip from a confidential informant that Lee had sold the informant ecstasy and marijuana. After obtaining a warrant, the officials searched Lee’s house, where they found drugs, cash, and a loaded rifle. Lee admitted that the drugs were his, and a grand jury indicted him on one count of possessing ecstasy with in- tent to distribute. Lee retained counsel and entered into plea discussions with the Government. During the plea process, Lee repeatedly asked his attorney whether he would face deportation; his attorney assured him that he would not be deported as a result of pleading guilty. Based on that assurance, Lee accepted a plea and was sentenced to a year and a day in prison. Lee had in fact pleaded guilty to an “aggravated felony” under the Immigration and Nationality Act, 8 U. S. C. §1101(a)(43)(B), so he was, contrary to his attorney’s advice, subject to mandatory deportation as a result of that plea. See §1227(a)(2)(A)(iii). When Lee learned of this consequence, he filed a motion to vacate his conviction and sentence, arguing that his attorney had provided constitutionally ineffective assistance. At an evidentiary hearing, both Lee and his plea-stage counsel testified that “deportation was the determinative issue” to Lee in deciding whether to accept a plea, and Lee’s counsel acknowledged that although Lee’s defense to the charge was weak, if he had known Lee would be de- ported upon pleading guilty, he would have advised him to go to trial. A Magistrate Judge recommended that Lee’s plea be set aside and his conviction vacated. The District Court, however, denied relief, and
JAE LEE v. UNITED STATES Syllabus
the Sixth Circuit affirmed. Applying the two-part test for ineffective assistance claims from Strickland v. Washington, 466 U. S. 668, the Sixth Circuit concluded that, while the Government conceded that Lee’s counsel had performed deficiently, Lee could not show that he was prejudiced by his attorney’s erroneous advice.
Held: Lee has demonstrated that he was prejudiced by his counsel’s erroneous advice. Pp. 5–13.
(a) When a defendant claims that his counsel’s deficient perfor- mance deprived him of a trial by causing him to accept a plea, the de- fendant can show prejudice by demonstrating a “reasonable probability that, but for counsel’s errors, he would not have pleaded guilty and would have insisted on going to trial.” Hill v. Lockhart, 474 U. S. 52, 59.
Lee contends that he can make this showing because he never would have accepted a guilty plea had he known the result would be deportation. The Government contends that Lee cannot show prejudice from accepting a plea where his only hope at trial was that something unexpected and unpredictable might occur that would lead to acquittal. Pp. 5–8.
(b) The Government makes two errors in urging the adoption of a per se rule that a defendant with no viable defense cannot show prejudice from the denial of his right to trial. First, it forgets that categorical rules are ill suited to an inquiry that demands a “case-by-case examination” of the “totality of the evidence.” Williams v. Taylor, 529 U. S. 362, 391 (internal quotation marks omitted); Strickland, 466 U. S., at 695. More fundamentally, it overlooks that the Hill v. Lockhart inquiry focuses on a defendant’s decisionmaking, which may not turn solely on the likelihood of conviction after trial.
The decision whether to plead guilty also involves assessing the respective consequences of a conviction after trial and by plea. See INS v. St. Cyr, 533 U. S. 289, 322–323. When those consequences are, from the defendant’s perspective, similarly dire, even the smallest chance of success at trial may look attractive. For Lee, deportation after some time in prison was not meaningfully different from deportation after somewhat less time; he says he accordingly would have rejected any plea leading to deportation in favor of throwing a “Hail Mary” at trial. Pointing to Strickland, the Government urges that “[a] defendant has no entitlement to the luck of a lawless deci- sionmaker.” 466 U. S., at 695. That statement, however, was made in the context of discussing the presumption of reliability applied to judicial proceedings, which has no place where, as here, a defendant was deprived of a proceeding altogether. When the inquiry is focused on what an individual defendant would have done, the possibility of even a highly improbable result may be pertinent to the extent it
Cite as: 582 U. S. ____ (2017) 3
would have affected the defendant’s decisionmaking. Pp. 8–10.
(c) Courts should not upset a plea solely because of post hoc assertions from a defendant about how he would have pleaded but for his attorney’s deficiencies. Rather, they should look to contemporaneous evidence to substantiate a defendant’s expressed preferences. In the unusual circumstances of this case, Lee has adequately demonstrated a reasonable probability that he would have rejected the plea had he known that it would lead to mandatory deportation: Both Lee and his attorney testified that “deportation was the determinative issue” to Lee; his responses during his plea colloquy confirmed the importance he placed on deportation; and he had strong connections to the United States, while he had no ties to South Korea.
The Government argues that Lee cannot “convince the court that a decision to reject the plea bargain would have been rational under the circumstances,” Padilla v. Kentucky, 559 U. S. 356, 372, since deportation would almost certainly result from a trial. Unlike the Government, this Court cannot say that it would be irrational for someone in Lee’s position to risk additional prison time in exchange for holding on to some chance of avoiding deportation. Pp. 10–13.
825 F. 3d 311, reversed and remanded.
ROBERTS, C. J., delivered the opinion of the Court, in which KENNEDY, GINSBURG, BREYER, SOTOMAYOR, and KAGAN, JJ., joined. THOMAS, J., filed a dissenting opinion, in which ALITO, J., joined except as to Part I. GORSUCH, J., took no part in the consideration or decision of the case.
My favorite quote from the Chief Justice’s opinion:
“There is no reason to doubt the paramount importance Lee placed on avoiding deportation. Deportation is always “a particularly severe penalty,” Padilla, 559 U. S., at 365 (internal quotation marks omitted), and we have “recognized that ‘preserving the client’s right to remain in the United States may be more important to the client than any potential jail sentence,’” id., at 368 (quoting St. Cyr, 533 U. S., at 322; alteration and some internal quotation
12 JAE LEE v. UNITED STATES Opinion of the Court
marks omitted); see also Padilla, 559 U.S., at 364 (“[D]eportation is an integral part—indeed, sometimes the most important part—of the penalty that may be imposed on noncitizen defendants who plead guilty to specified crimes.” (footnote omitted)). At the time of his plea, Lee had lived in the United States for nearly three decades, had established two businesses in Tennessee, and was the only family member in the United States who could care for his elderly parents—both naturalized American citizens. In contrast to these strong connections to the United States, there is no indication that he had any ties to South Korea; he had never returned there since leaving as a child.”
When is the Court finally going to take the next logical step, ditch the fiction that “deportation from the United States is strictly a civil matter,” and formally recognize that deportation, at least of someone like Lee who has been legally admitted to the U.S. for permanent residence, is indeed punishment, of the severest type imaginable! Indeed, exile as punishment dates back to ancient times?
Also worthy of note, the DOJ and the Solicitor General continue to be spectacularly unsuccessful in convincing a conservative, law enforcement oriented Court of the merits of their extreme “hard-line” positions in immigration-related matters. I have previously predicted that loss of “face” and credibility by the SG before the Supremes is a likely consequence of representing the Trump Administration with Jeff Sessions as your boss. As the President himself is finding out, the hard way, once lost, credibility before the courts is difficult or impossible to regain.