By Daniel Horwitz:
The United States Supreme Court has agreed to hear a Sixth Amendment case out of Tennessee in its March 2017 sitting. The case – Jae Lee v. United States – focuses on the Sixth Amendment’s guarantee of effective assistance of counsel when plea bargains trigger deportation consequences. Specifically, Jae Lee will determine whether a defendant who would likely have been convicted if he had proceeded to trial is prejudiced by ineffective counsel when he accepts a guilty plea on the basis of erroneous legal advice that he will not be deported.
The facts of Jae Lee are not in dispute. In 1982, Mr. Lee legally immigrated to the United States from South Korea. Thereafter, Mr. Lee completed high school and moved to Memphis with his family, where he became a successful restaurateur. As the Sixth Circuit noted, however, Mr. Lee “also became a small-time drug dealer,” and in 2009, he “was charged with possession of ecstasy with intent to distribute” in violation of federal drug laws. If convicted, Mr. Lee would immediately become deportable. Unfortunately for Mr. Lee and his family, the case against him was also very strong.
After being indicted, Mr. Lee’s criminal defense attorney advised him to plead guilty in exchange for a lighter sentence. Mr. Lee’s attorney also advised him that if he accepted a guilty plea, he would not be deported. On the basis of that advice, Mr. Lee decided to plead guilty.
Unfortunately for Mr. Lee, the advice that he received from his attorney turned out to be spectacularly wrong. Notwithstanding his attorney’s advice to the contrary, Mr. Lee’s guilty plea actually did render him deportable, and he was immediately subjected to removal proceedings as a result. Had he avoided a criminal conviction or been convicted of a different offense, however, Mr. Lee would have been permitted to remain in the country.
Understandably upset that he had pleaded guilty based on legal advice that turned out to be completely incorrect, Mr. Lee sought to withdraw his guilty plea on the basis that he had received the ineffective assistance counsel. Under the standard for ineffective assistance of counsel established in Strickland v. Washington, a defendant must satisfy two separate requirements in order to prevail. First, a defendant must demonstrate that his attorney’s performance was “deficient” in that it fell below prevailing professional norms. Second, the defendant must demonstrate that he suffered legal “prejudice” as a consequence of his counsel’s deficient performance. Both requirements must be met in order to win a claim of ineffective assistance of counsel, which – if successful – would have allowed Mr. Lee to withdraw his guilty plea and proceed to trial instead.
Because the government conceded that Mr. Lee’s attorney had rendered deficient counsel by misadvising him about the deportation consequences of accepting a guilty plea, the only question remaining was whether Mr. Lee was legally “prejudiced” by his attorney’s erroneous advice. Typically, a defendant challenging a conviction on the basis of ineffective assistance of counsel must prove that there is “a reasonable probability that, but for counsel’s unprofessional errors, the result of the proceeding would have been different.” Importantly, however, when it comes to plea bargaining, the test for prejudice is slightly more favorable to defendants. Generally, to withdraw a guilty plea on the basis of ineffective counsel, a defendant must show “a reasonable probability that, but for counsel’s errors, he would not have pleaded guilty and would have insisted on going to trial.” As this author explains in his 2016 Harvard Latino Law Review article on this subject, however, following the U.S. Supreme Court’s landmark 2010 decision in Padilla v. Kentucky, immigration-related pleas have a different standard still. Specifically:
“In the context of deficient immigration counsel,  the test is whether ‘a decision to reject the plea bargain would have been rational under the circumstances.’ It is not yet clear whether, or to what extent, there is a substantive difference between these standards, and indeed, the Government occasionally ‘wobbles between the two standards for allowing the withdrawal of one’s guilty plea upon belated discovery of the deportation threat.’ What is clear, however, is that the test for prejudice under Padilla is not whether a defendant would have been deported anyway. Instead, it is whether the defendant would rationally have rejected the offered plea bargain and either proceeded to trial or negotiated an alternative plea bargain if the defendant had received the competent immigration counsel to which all immigrants are constitutionally entitled.”
The federal Circuits are deeply divided on whether it can ever be “rational” for an obviously guilty defendant to reject a plea bargain and instead attempt to “throw a Hail Mary” at trial in the hopes of avoiding near-certain deportation consequences. After acknowledging this split of authority, the Sixth Circuit reaffirmed its prior holding in Pilla v. United States that “no rational defendant charged with a deportable offense and facing ‘overwhelming evidence’ of guilt would proceed to trial rather than take a plea deal with a shorter prison sentence.” Accordingly, the Sixth Circuit denied Mr. Lee an opportunity to withdraw his guilty plea, and the Supreme Court granted review.
The problem with the Sixth Circuit’s (and several other Circuits’) take on this issue, however, is that it misapplies the standard for prejudice under Padilla and also violates the bedrock constitutional requirement that a guilty plea must be entered voluntarily. As Judge Posner of the Seventh Circuit wrote in a similar case, for example, “[j]udges and prosecutors should hesitate to speculate on what a defendant would have done in changed circumstances,” and “a criminal defendant cannot be denied the right to a trial, and forced to plead guilty, because he has no sturdy legal leg to stand on but thinks he has a chance that the jury will acquit him even if it thinks he’s guilty.” Additionally, as this author explains in his Harvard Latino Law Review article referenced above, “several commentators have recognized the reality that in most instances, non-citizen defendants are likely to view deportation as a far more serious punishment than a conviction that results in incarceration.” Thus:
By any metric, a defendant who accepts a guilty plea as a consequence of  affirmative misadvice [that he will not be deported]—only to learn later on that he is to be deported anyway—has suffered serious prejudice in the form of a criminal conviction due to his counsel’s incompetence.
This sort of bait-and-switch—which, incidentally, occurred in Padilla itself—represents a classic case of ineffective assistance of counsel. Indeed, on this point, even the two concurring Justices in Padilla enthusiastically agreed. As Justice Alito explained:
when a defendant bases the decision to plead guilty on counsel’s express misrepresentation that the defendant will not be removable[,] . . . it seems hard to say that the plea was entered with the advice of constitutionally competent counsel—or that it embodies a voluntary and intelligent decision to forsake constitutional rights [at all].
Daniel A. Horwitz, Actually, Padilla Does Apply to Undocumented Defendants, 19 Harv. Latino L. Rev. 1, 19 (2016).
Consequently, given that fully seven of the Supreme Court’s eight current Justices have held that a defendant cannot be denied the opportunity to withdraw a guilty plea under these circumstances, it seems likely that Mr. Lee – and his excellent Tennessee attorney Patrick McNally – will ultimately prevail.
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 825 F.3d 311 (6th Cir. 2016), cert. granted, No. 16-327, 2016 WL 4944484 (U.S. Dec. 14, 2016).
 466 U.S. 668, 687 (1984).
 Id. at 694.
 Hill v. Lockhart, 474 U.S. 52, 59, 106 S.Ct. 366, 88 L.Ed.2d 203 (1985).
 559 U.S. 356 (2010).
 Daniel A. Horwitz, Actually, Padilla Does Apply to Undocumented Defendants, 19 Harv. Latino L. Rev. 1, 15 (2016) (citations omitted).
 Compare Pilla v. United States, 668 F.3d 368, 373 (6th Cir. 2012); Haddad v. United States, 486 Fed. Appx. 517, 521–22 (6th Cir. 2012); Kovacs v. United States, 744 F.3d 44, 52–53 (2d Cir. 2014); United States v. Akinsade, 686 F.3d 248, 255–56 (4th Cir. 2012); and United States v. Kayode, 777 F.3d 719, 724–29 (5th Cir. 2014), with United States v. Orocio, 645 F.3d 630, 643–46 (3d Cir. 2011), abrogated on other grounds by Chaidez v. United States, ––– U.S. ––––, 133 S.Ct. 1103, 185 L.Ed.2d 149 (2013); DeBartolo v. United States, 790 F.3d 775, 777–80 (7th Cir. 2015); United States v. Rodriguez–Vega, 797 F.3d 781, 789–90 (9th Cir. 2015); Hernandez v. United States, 778 F.3d 1230, 1234 (11th Cir. 2015).
 DeBartolo v. United States, 790 F.3d 775, 778-89 (7th Cir. 2015).