Lee v. United States: Vacating a Criminal Conviction Based On Ineffective Assistance Regarding Immigration

Lee v. United States



On June 23, 2017, the Supreme Court of the United States issued its decision in Lee v. United States, 582 U.S. ___ (2017) [PDF version]. The case concerned Jae Lee, an alien who had been a defendant in criminal proceedings. Lee's counsel incorrectly advised him that pleading guilty to certain criminal charges would not have adverse immigration consequences. Lee pled guilty, but he was then charged as deportable on the basis of the offense to which he had pled guilty. In moving to vacate his conviction Lee claimed that his counsel had been ineffective and asserted that, had he given legally accurate advice, Lee would have opted to go to trial in lieu of pleading guilty.

A six-justice majority led by Chief Justice John Roberts held that a defendant can show prejudice from his counsel's deficient performance in plea proceedings by establishing that there is a reasonable probability that but for counsel's errors, he or she would not have pled guilty. Pertinently, this standard thus applies regardless of the presumptive strength of the evidence against the defendant and the likely outcome if a trial were to have taken place. The Supreme Court also held that courts should look for evidence of the circumstances from the time of the plea to determine if the defendant would have declined the plea deal but for the erroneous advice of his or her counsel.

In this article, we will examine the facts of the case, the analysis and decision in the majority opinion, and what this new precedent will mean in the immigration context going forward. We will also examine in brief the dissenting opinion authored by Justice Clarence Thomas and joined by Justice Samuel Alito. Please note that Justice Neil Gorsuch took no part in the consideration of the case.

Opinion of the Court: Chief Justice Roberts

Chief Justice John Roberts, writing also for Justices Anthony Kennedy, Ruth Bader Ginsburg, Stephen Breyer, Sonia Sotomayor, and Elena Kagan, delivered the Opinion of the Court. In the subsequent sections, we will examine Chief Justice Roberts' opinion.

Part I: Facts and Procedural History

The petitioner, Jae Lee, a native and citizen of South Korea, was a lawful permanent resident (LPR) of the United States. He had lived in the United States for 35 years and had never returned to South Korea since arriving in the United States at the age of 13.

In 2008, law enforcement officials obtained a search warrant for Lee's house. They found 88 ecstasy pills, three Valium tablets, $32,432 in cash, and a loaded rifle. Lee admitted to law enforcement officials that the ecstasy pills were his and that he had given ecstasy to his friends.

Lee was indicted on one count of possessing ecstasy with the intent to distribute in violation of 21 U.S.C. 841(a)(1). Lee obtained counsel and entered into plea negotiations with the Government. Lee's attorney advised him that going to trial would be “very risky.” Furthermore, Lee's counsel informed him that, by pleading guilty, he would receive a lighter sentence than if he were to be convicted at trial.

Lee informed his counsel that he was an LPR and asked about the potential immigration consequences of a guilty plea. Lee's counsel told him that he would not be deported as a result of pleading guilty.

On the basis of this assurance that pleading guilty would not render him deportable, Lee accepted the Government's plea offer. The District Court sentenced Lee to one year and one day in prison. The District Court deferred commencement of Lee's sentence for two months.

After pleading guilty, Lee discovered that he had in fact pled to an “aggravated felony” under the immigration laws found in section 8 U.S.C 1101(a)(43)(B) (see section 101(a)(43)(B) of the Immigration and Nationality Act (INA)). On account of having pled guilty to an aggravated felony, Lee was subject to the deportability provision found in 8 U.S.C. 1227(a)(2)(A)(iii) (see section 237(a)(2)(A)(iii) of the INA).

Having discovered that his guilty plea rendered him deportable, Lee filed a motion under 28 U.S.C. 2255 to vacate his conviction. He argued that his attorney had provided constitutionally ineffective assistance by providing incorrect guidance regarding the immigration consequences of a guilty plea.

At an evidentiary hearing on Lee's motion to vacate, both Lee and his plea-stage counsel testified that deportation was the determinative issue in Lee's decision of whether to accept the guilty plea. Lee testified that his attorney repeatedly reassured him during the plea proceedings that he did not need to worry about his immigration status. Lee's attorney assured him that “the government cannot deport you.” Lee's attorney advised him to take the plea because of the weakness of their case. Lee's attorney acknowledged that, had he understood the immigration ramifications of the guilty plea, he would have advised Lee to go to trial.

Based on the testimony of Lee and his plea-stage attorney, the Magistrate Judge recommended that Lee's plea be set aside and his conviction vacated due to his having received ineffective assistance of counsel. However, applying the four-part test from the Supreme Court decision in Strickland v. Washington, 466 U.S. 668 (1984) [PDF version], the District Court denied relief. The District Court agreed that Lee's counsel had performed deficiently in providing incorrect information about the immigration ramifications of a conviction, but it nevertheless denied relief in light of the substantial evidence establishing Lee's guilt, which suggested he would have not only been convicted had the case gone to trial, but that he would also have received “a significantly longer prison sentence, and subsequent deportation.” For this reason, the District Court held that Lee could not show that he had been prejudiced by his attorney's deficient performance.

On appeal, the United States Court of Appeals for the Sixth Circuit affirmed the District Court's decision to deny relief in its decision titled Lee v. United States, 825 F.3d 311 (6th Cir. 2016) [PDF version]. Before the Sixth Circuit, the Government conceded that Lee's attorney had been deficient in the plea-stage. However, the Sixth Circuit held, citing to the Supreme Court's application of the Strickland analysis to the guilty plea scenario in Hill v. Lockhart, 474 U.S. 52, 59 (1985) [PDF version], that Lee was required to show that, but for the deficient advice, he would not have pled guilty. Agreeing with the District Court, the Sixth Circuit held that, because Lee had lacked a bona fide defense (or even a weak defense), he had nothing to gain from going to trial. Relying on its own precedent, the Sixth Circuit concluded that no rational defendant charged with a deportable offense facing overwhelming evidence of guilt would opt to go to trial in lieu of taking a plea deal with a shorter prison sentence.

Lee appealed from the Sixth Circuit decision to the Supreme Court, which agreed to hear the case.

Part II-A: Setting Forth the Issues

Citing to Strickland, 466 U.S., at 694, Chief Justice Roberts explained that the standard for establishing ineffective assistance of counsel during the course of a legal proceeding is whether the defendant can show not only that the attorney's performance was deficient but also that there is a “a reasonable probability that, but for counsel's unprofessional errors, the result of the proceeding would have been different.”

However, Lee v. United States involved not a “judicial proceeding of disputed reliability, but rather [] the forfeiture of a proceeding itself.” Roe v. Flores-Ortega, 528 U.S. 470, 483 (2000) [PDF version]. Again citing to Flores-Ortega, the Chief Justice explained that when a defendant alleges that his attorney's deficient performance led him to accept a guilty plea instead of going to trial, the question is not whether the result of the trial would have been different than the plea bargained result. Rather, the question is whether the defendant was prejudiced by foregoing a trial due to the deficient performance of his attorney. Id. Citing to Hill, 474 U.S. at 59, the Chief Justice explained that a defendant alleging ineffective assistance of counsel in the plea stage may establish 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” regardless of the weight of the evidence of his guilt.

Chief Justice Roberts noted that the dissenting opinion of Justice Clarence Thomas [see section] took the position that the defendant must show additionally that he or she would have been better off going to trial than as resulted from the plea. However, Chief Justice Roberts and the majority held that this standard only applies “when the defendant's decision about going to trial turns on his prospects of success and those affected by his attorney's error…” Such was not the scenario presented in Lee's case. Chief Justice Roberts explained that Lee knew that his prospects of acquittal at trial were grim. However, Lee's attorney's error had nothing to do with an assessment of the likely outcome of a trial relative to the offered disposition of the charge. Instead, the error affected Lee's understanding of the immigration consequences of pleading guilty.

Citing again to Hill, Chief Justice Roberts explained that instead of asking how a hypothetical trial would have played out but for the attorney error, the Court was to consider “whether there was an adequate showing that the defendant, properly advised, would have opted to go to trial.”

Lee insisted that had he been given the correct advice in the plea stage regarding the immigration ramifications of a guilty plea, he would have rejected the plea offer and opted to risk going to trialon the off chance he might be acquitted, while fully understanding that he faced the potential of significantly more jail time in doing so. The Government responded by noting that due to the evidence against Lee, he would have almost certainly lost at trial, and have received a longer prison sentence, and would still have been subject to deportation,. Accordingly, the Government urged the Court to find that Lee could not establish prejudice, as required by Strickland v. Washington, “where his only hope at trial was that something unexpected and unpredictable might occur that would lead to an acquittal.”

Part II-B Rejecting the Government's Position

The Government urged the Supreme Court to adopt a per rule described by the Chief Justice thus: “[T]hat a defendant with no viable defense cannot show prejudice from the denial of his right to trial.” Chief Justice Roberts found that the Government's position may make sense in certain cases, but the proposal failed as a general rule for the following reasons:

1. 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 (2000) [PDF version]); and
2. Under Hill, the inquiry depends on the defendant's decision making, which may not always hinge on the likelihood of conviction post-trial.

Chief Justice Roberts acknowledged that, in most cases, a defendant without any viable defense to the charges against him or her would be unable to show prejudice from accepting a guilty plea that provides a better outcome for the defendant than what would have been likely had he or she opted to go to trial.

However, the Chief Justice explained that sometimes there is more to consider in weighing a plea offer than success at trial. Citing to INS v. St. Cyr, 533 U.S. 289, 322-323 (2001) [PDF version], Chief Justice Roberts noted that the decision of whether to accept a plea also takes into account the consequences of a conviction after trial and plea. In the event that, from the defendant's perspective, the consequences are “similarly dire,” the defendant may be more likely to choose to go to trial. In the instant case, Lee testified that avoiding deportation was the determinative factor for him. Accordingly, for Lee, deportation after a shorter prison sentence under the plea deal was not meaningfully different than deportation after the likely longer prison sentence stemming from a trial. Lee stated that he would have risked the longer sentence for the very slight chance that he could have avoided a conviction that would lead to his deportation.

Citing to Strickland, 466 U.S., at 695, the Government took the position that a “defendant has no entitlement to the luck of a lawless decisionmaker.” However, Chief Justice Roberts found that this standard is not relevant where the defendant was deprived altogether of a proceeding, namely, a trial. Instead, the question is what the defendant would have done regarding the plea had counsel not been deficient.

Part II-C: Rule Going Forward

Chief Justice Roberts held that “[j]udges should [] look to contemporaneous evidence to substantiate a defendant's expressed preferences.” Here, he means that it is not sufficient for a defendant to simply claim, after the fact, that he would have pled differently but for the deficient performance of his or her attorney. Rather, the Court must assess all of the evidence in order to substantiate the defendant's claim.

In the instant case, the Court held that Lee sustained his burden of demonstrating a reasonable probability that he would have rejected the plea deal had he known that it would lead to his mandatory deportation. The Chief Justice found that there was “no question” that avoiding deportation was determinative for Lee. At the hearing on the motion to vacate, both Lee and his attorney had testified that Lee would not have gone to trial had he understood the immigration consequences of the plea. Furthermore, when entering his plea, Lee's attorney had assured him that the judge's warning that the conviction could have immigration consequences was a “standard warning” and that Lee had no reason to worry. Citing to Padilla v. Kentucky, 559 U.S. 356, 365 (2010) [PDF version], the Chief Justice noted that deportation is “a particularly severe penalty.” In St. Cyr, 533 U.S., at 32, the Court noted that preserving the right to remain in the United States may be more important to defendants in some cases than the length of a jail sentence.

Chief Justice Roberts rejected the Government's argument that Lee had to establish that rejecting the plea would have been rational in light of the circumstances. The Chief Justice stated that, because the paramount concern for Lee was avoiding deportation, preserving a slight chance of avoiding deportation was not an irrational choice, even though others similarly situated may have weighed the factors different (also noting Lee's strong connections to the United States).

Dissent: Justice Thomas (Joined by Justice Alito in Part)

Justice Clarence Thomas filed a dissenting opinion, joined by Justice Samuel Alito but for Part I of the dissent. In this post, we will examine the dissenting opinion.

Part I: Justice Thomas Alone

Citing to the dissenting opinion of Justice Scalia in Padilla, 559 U.S., at 388 (Scalia, J., joined by Thomas, J., dissenting), Justice Thomas asserted his continuing position that the Sixth Amendment to the United States Constitution does not require that counsel provide a defendant with accurate advice concerning the potential removal or deportation consequences of a guilty plea. Justice Thomas would have affirmed the Sixth Circuit on this ground. Justice Alito did not join in this part of Justice Thomas's dissent, which should come as no surprise considering the fact that Justice Alito did not join with the dissent in Padilla.

Brief Overview of Parts II-IV: Justice Thomas joined by Justice Alito

Justices Thomas and Alito agreed with the Government's position — and that of the Sixth Circuit — that Lee had the burden of showing that the deficient representation he received had an adverse effect on his defense.” Strickland 466 U.S., at 688, 693. Citing to Id., at 694, Justice Thomas would have held that Lee had to establish that, but for the error of his attorney, the result of the proceedings would have been different. In other words, not only that he would have chosen to stand trial, but also that there was a reasonable probability that he would have been able to procure a better result from a trial. Furthermore, Justice Thomas noted that Hill in fact incorporated this Strickland test into the plea proceeding context. In Premo v. Moore, 562 U.S. 115 (2011) [PDF version], Justice Thomas noted that the Court held that “strict adherence to the Strickland standard” applies when evaluating ineffective assistance claims at the plea stage.

Justice Thomas also cited to Missouri v. Frye, 566 U.S. 134 (2012) [PDF version]. In Frye, the Court held that counsel could be held to be ineffective for failing to communicate a plea offer to the defendant. However, Justice Thomas also characterized the decision as requiring a reasonable probability that the result of the criminal process would be more favorable by reason of plea to a lesser charge or less prison time. Id., at 147, 150. (Note that Chief Justice Roberts disagreed with Justice Thomas's analysis of Frye.)

Justice Thomas argued that the majority misapplied Supreme Court precedent in concluding that the defendant could establish prejudice without showing that the result of the trial would be any different than the plea bargain. Justice Thomas also argued that Roe v. Flores-Ortega, relied upon in sections by Chief Justice Roberts, was not relevant because the case dealt with a defendant's claim that his attorney had failed to file a notice of appeal.

Regarding Hill, Justice Thomas took the position that “Hill instructs that the prejudice inquiry must presume that the foregone trial would have been reliable.” In a broader point, Justice Thomas criticized the Court for what he described as applying different standards for ineffectiveness claims for when a case goes to trial (Strickland), when the defendant accepts a plea (Hill), and when the defendant rejects a plea (Frye).

Applying his reading to the instant case, Justice Thomas would have ruled against Lee because Lee could not show a reasonable probability that the result of his criminal proceeding would have been different had he not pled guilty. Justice Thomas further noted that the necessarily implication would that Lee would have faced deportation regardless.

Finally, Justice Thomas expressed concern about the potential effect of the decision going forward. Citing to Primeo, 562 U.S., at 125, Justice Thomas noted that the effect of the Court's permissive standard in the instant case could compel prosecutors to forgo plea bargains in certain cases. In conclusion, Justice Thomas stated: “In circumstances where a defendant has admitted his guilt, the evidence against him is overwhelming, and he has no bona fide defense strategy, I see no justification for imposing [the potential] costs.”


Lee is a significant decision in both the immigration and broader criminal law contexts. Under Lee, an individual seeking to vacate a guilty plea based on counsel having misadvised him of the immigration repercussions of his plea need only show that counsel's performance was deficient and that, but for the deficient performance, the alien would not have pled guilty. Notably — and to the consternation of Justices Thomas and Alito — the Court did not require that the individual establish that he or she had any likelihood of achieving a superior result in going to trial.

It is worth noting that it is unclear from the decision to the extent which, if at all, Lee will apply retroactively. This remains to be seen in subsequent litigation.

Whether Lee applies in any given case will rely upon a fact-specific inquiry. An alien who is facing immigration issues relating to a guilty plea should consult with an experienced immigration attorney for case-specific guidance. When an alien is facing criminal charges, it is essential that he or she consult with an attorney who understands the immigration laws in order to have the best advice at each stage of the process, and with hope, avoid pleading guilty or making any other decision based on faulty information.