Lee v. U.S.: Plea Bargains, Deportation, and Very, Very Strange Bedfellows

Present political situation aside, America is pretty awesome. To quote our first treasury secretary, it’s the land “where even orphan immigrants can leave their fingerprints and rise up.” And that is why the case of Lee v. U.S. is so interesting: it asks, when faced with overwhelming odds of conviction and automatic deportation, is it ever rational for a criminally-charged lawful permanent resident to risk trial in a Hail Mary attempt to avoid deportation? According to Petitioner Jae Lee, the answer is yes. The U.S. government, however, disagrees. The case will be argued at the Supreme Court this week.

At 13 years old, Jae Lee moved from South Korea with his parents. For whatever reason, while he maintained legal permanent residency, he never obtained his U.S. citizenship. Lee developed a drug problem and in 2009 was arrested and charged with possession of ecstasy with an intent to distribute.

When contemplating a potential plea bargain, Lee made clear to his attorney that his primary priority was avoiding deportation, even at the expense of a shorter sentence. His attorney incorrectly advised him that if he took the plea offered by the government of pleading guilty to possession with intent to distribute in exchange for a shorter sentence, he would not and could not be deported. In reality, deportation was a mandatory penalty for the crime for which he had just been convicted, and deportation proceedings were promptly instituted.

Lee appealed on the basis that he received ineffective assistance of counsel. Under the Supreme Court’s decision in Strickland v. Washington, 466 U.S. 668 (1984), a defendant asserting a claim of ineffective assistance of counsel must not just prove that his attorney’s representation was “deficient”, but also that the defendant was “prejudiced” as a result. The parties agree that the first element is met; indeed, the Supreme Court ruled in Padilla v. Kentucky, 559 U.S. 356, that a lawyer provides ineffective counsel when he fails to tell a client that pleading guilty will subject the defendant to deportation.

The case thus centers on the second element: was Jae Lee actually prejudiced as a result of his attorney’s plainly deficient advice? Despite the gut reaction being “obviously”, the Sixth Circuit said no, basing their decision on the aforementioned Padilla case, which stated that “to obtain relief on this type of claim, a petitioner must convince the court that a decision to reject the plea bargain would have been rational under the circumstances.”

The Sixth Circuit reasoned that it would not have been objectively rational to reject the offered plea because Lee had no real chance of avoiding deportation due to overwhelming evidence of his guilt, and because there was no real prospect of pleading down to a non-deportable offense. According to the Sixth Circuit, “being denied the chance to throw a Hail Mary at trial does not by itself amount to prejudice.” Lee, on the other hand, essentially argues that with nothing to lose deportation-wise, it would have been perfectly rational to “risk it” at trial. Thus, by depriving Lee of this option, Lee was prejudiced. It bears mentioning that circuit courts are deeply split on this very issue, with the Third, Seventh, Ninth and Eleventh Circuits finding for defendants in Lee’s situation, and the Second, Fourth, Fifth and Sixth (both here and in a prior decision) Circuit Courts finding against similarly-situated defendants.

At issue is not just Lee’s fate, but also the Court’s view of the state of plea bargaining in this country. To that end, the case makes for strange alliances and bedfellows. Liberal criminal justice reformers criticize the system as a plea bargaining mill, where under 5 percent of cases go to trial and the other 95% defendants plea rather than risking trial. This criticism of plea bargaining underscores Jae Lee’s argument and was discussed in amicus briefing in Lee’s favor. Representing Lee, however, is not the ACLU or a liberal interest group, but rather John J. Bursch, the conservative former Michigan Solicitor General who had been floated as a possible Trump pick for Solicitor General, and who has argued before the Supreme Court ten times. The most notable of these appearance was in Obergefell v. Hodges, when he argued on behalf of the states against gay marriage. In another case before the high court, Lafler v. Cooper, 566 U.S. __ (2012), during his stint as Michigan’s Solicitor General, Bursch argued against a criminal defendant’s ineffective assistance claim under Strickland. Suffice it to say, representing a likely-guilty drug-dealing immigrant against the government’s attempts to deport him is not a typical situation for him. In fact, twenty states – all of which were won by Trump, including Bursch’s home state of Michigan – filed an Amicus Brief against Lee and for the U.S. government. That Lee is represented by Bursch instantly provides conservative gravitas and legitimacy to his argument.

On the other side, we have the United States government, paradoxically arguing that remaining in America is not great enough to risk jail time for. That is obviously an over-simplification of their position, but hits at the gravamen of Lee’s argument – that it is sometimes rational for an immigrant to risk trial and extended jail time in order to maintain a sliver of hope of remaining in this country.

In a perfectly logical way, the government’s position makes sense – Lee cannot prove prejudice because he cannot show that his attorney’s ineffectiveness plausibly led to a worse outcome, since Lee’s conviction and deportation were almost certain to occur. But it’s the “almost” part of “almost certain” that is key. Like all citizens, Lee has a constitutional right to a jury trial and a presumption of innocence, and that was taken from him directly because of his attorney’s deficiency. However unlikely, Lee could have won – at least on the deportation-mandatory “intent to distribute” charge. Lee also may have obtained a more favorable plea on lesser, non-deportable charges later in the proceedings.

Going to trial to maintain that sliver of hope is objectively reasonable, even at the risk of a longer jail sentence. For an immigrant, remaining “in the United States may be more important than any potential jail sentence.” Padilla, at 368. Not just to Jae Lee, but to other immigrants as well. Lee’s attorney, Bursch – who personally argued against gay marriage in the Supreme Court – persuasively provides the example of a legal immigrant from Nigeria who is LGBT and would face potential death if returned to his home country. To that defendant, taking his chances at trial is certainly objectively rational. Bursch then cites to an article listing ten countries where homosexuality is punishable by death. This argument serves as the piece de resistance of Lee’s brief, and it is even more stunning considering the source.

That Bursch is the one making this argument may actually be the thing that wins the day for Lee. It would be very easy for Chief Justice Roberts and other conservatives in the “calling balls and strikes” crowd to write Lee’s case off as an unfortunate but straightforward application of existing precedent. But Bursch’s involvement complicates things, and it may create a subconscious permission structure for at least some of the conservatives (i.e. Roberts and Kennedy) to find for Lee. Again, this isn’t the Southern Poverty Law Center making this argument, it is a prominent conservative appellate lawyer who has spent his career representing governments and defending conservative positions.

Ultimately, Chief Justice Roberts and Justice Kennedy will likely be the deciding votes, and it remains to be seen whether they or the other justices will be swayed by Lee’s logic. But it certainly appears to me to be an instance when risking near-certain conviction at trial would be objectively favorable to a plea to reduce prison time.