The Supreme Court has settled a dispute lingering in the lower courts since its decision seven years ago in Padilla v. Kentucky:  If a criminal defendant’s decision to plead guilty resulted from his lawyer’s constitutionally deficient advice about the collateral consequences of conviction, what does he have to show to undo the plea and bring the government back to the bargaining table?  The question before the Court in Jae Lee v. United States was whether a defendant facing deportation must be given a second chance to stay in the United States after bad advice from his lawyer led him to plead guilty, even though the odds of his winning at trial are low and he is likely to be deported anyway.

The government argued that no “rational” defendant in Lee’s position would have risked a longer prison term, that he therefore could not show that he was prejudiced by his lawyer’s bad advice, and that the plea should accordingly stand.  Lee countered that “deportation after some time in prison was not meaningfully different from deportation after somewhat less time,” and that he would have taken his chances with the jury if he had had accurate advice about the consequences of pleading guilty.  As the Court put it, he “would have rejected any plea leading to deportation in favor of throwing a ‘Hail Mary’ at trial.”

On June 23, the Supreme Court agreed that Lee should have another bite at the apple. In an opinion by Chief Justice Roberts, the Court held 6-2 that Lee had met his burden of showing that it would not have been “irrational” for him to reject the plea offer and go to trial, even though he would have been “almost certain” to lose.

The Court’s opinion is analyzed by Amy Howe at SCOTUSblog here.  Justices Thomas and Alito dissented, and Justice Gorsuch took no part in the decision.