Over 95% of criminal cases in the federal system end in a plea bargain, rather than going to trial. One such case is that of Jae Lee, who in 2009 pleaded guilty to possession of ecstasy with the intent to distribute it. Lee was sentenced to one year and one day in prison – considerably less than the 24 to 30 months suggested by the U.S. Sentencing Guidelines.

The real problems began after Lee went to prison. In 1982, at the age of 13, Lee had moved from South Korea to the United States with his parents. They became U.S. citizens, but he did not. Lee’s attorney, Larry Fitzgerald, had told Lee before he entered his plea that he would not be deported: The government wasn’t seeking to deport him as part of the plea bargain, Fitzgerald explained, and because Lee had been in the country so long, the government couldn’t remove him from the country even if it wanted to. Fitzgerald’s advice, it turned out, was dead wrong. Lee learned that deportation was a mandatory penalty for the crime of which he had now been convicted.

Lee filed a petition seeking post-conviction relief on the ground that Fitzgerald had not provided him with the effective assistance of an attorney guaranteed by the Sixth Amendment. Fitzgerald indicated that, if he had known that Lee’s plea would result in mandatory deportation, he would have advised him to go to trial. But Fitzgerald also acknowledged that this was “a bad case to try” and that Lee likely would have received an even longer sentence after a jury trial. Both a federal district court and the U.S. Court of Appeals for the 6th Circuit turned Lee down.

Under the Supreme Court’s seminal decision in Strickland v. Washington, a defendant who wants to have his conviction overturned based on ineffective assistance by his lawyer must show two things: first, that his attorney’s representation was deficient; and, second, that he was prejudiced by that ineffective assistance. In Lee’s case, the U.S. government agrees that Fitzgerald’s assistance was inadequate. The dispute centers on the second prong of the Strickland test: whether Lee was prejudiced by Fitzgerald’s bad advice. The 6th Circuit agreed with the government that he was not, ruling instead that when there is “overwhelming evidence” that a defendant is guilty, he cannot be prejudiced by accepting a plea bargain. The Supreme Court agreed to weigh in last December.

In the Supreme Court, Lee argues that courts should apply a different rule to determinations of prejudice when the defendant is an immigrant. For an immigrant facing the prospect of deportation, Lee explains, the evidence suggesting his guilt is only one factor in his decision. He will also consider how long the prison sentence would be and the consequences for his immigration status. For someone who has been in the United States for a long time, he contends, staying in the country may be the ultimate goal, even if it means more jail time or taking one’s chances at trial. This is particularly true for immigrants who might face serious consequences if removed. For example, he observes, a Nigerian LGBT immigrant, if forced to return to Nigeria, would likely go to prison or even be killed. For that reason, it would not be irrational for him to go to trial. Therefore, Lee concludes, a defendant should be allowed to show “that he would have bargained for a different plea offense or taken his chances at trial rather than plead guilty to an offense that resulted in his permanent exile from the United States.”

If Fitzgerald had told him that he would face deportation if he pleaded guilty, Lee reasons, he would have tried to negotiate a different plea, even if it meant more jail time, that would not have endangered his ability to stay in the United States – for example, a plea to a charge of simple possession of ecstasy, rather than intent to distribute, which would have allowed him to try to avoid deportation. Other possibilities might have included an agreement not to prosecute or one that would have allowed him to enter a pretrial diversion program instead. And if he had opted to go to trial, Lee notes, trials can be unpredictable. Important witnesses sometimes fail to show up or evidence is suppressed, prompting prosecutors to offer a plea to a lesser charge.

The federal government counters that the Supreme Court’s decision in Strickland requires a defendant to demonstrate that there was an “objectively rational” reason for him to have spurned a plea offer and go to trial. A defendant can’t show that he was prejudiced by an attorney’s bad advice about the consequences that a plea deal would have on his immigration status when the evidence against him was “overwhelming” and there is no evidence that the government would have offered him a better deal that would have allowed him to avoid deportation. Lee’s approach, the government warns, would “effectively give dispositive weight to a defendant’s assertion that he would have thrown ‘a Hail Mary’ at trial had he known the immigration consequences of a conviction,” which would in turn virtually guarantee relief for all defendants in similar situations.

In Lee’s case, the government argues, he still would have been convicted because of the strong evidence against him, and he still would have been deported if he had gone to trial – the only difference would have been that he would have had to serve a longer prison sentence first. Although Lee suggests that the evidence discovered through a search of his house might have been suppressed in the end, the government maintains there was no real basis for such a challenge. But even if there had been a good argument for excluding the evidence, the government continues, the prosecutors also had a confidential informant who would have testified that he had purchased 200 ecstasy pills from Lee over eight years. Similarly, there is no reason to believe that the prosecutors would have offered Lee a much more lenient plea bargain that would have allowed him to avoid deportation.

Lee’s case does not have the high public profile of some of the others on the court’s docket this term – including Gloucester County School Board v. G.G., the transgender bathroom dispute that was originally also scheduled for oral argument next Tuesday. But given the ubiquity of plea deals in the criminal justice system and the apparent frequency with which criminal defendants receive bad advice about the immigration consequences of such pleas from their attorneys, this is a case that attorneys and advocates in the field of “crimmigration” will be watching closely.