Lee: A “Hail Mary” Can Be Rational When Deportation Is the Whole Case

You took the deal because your lawyer said you would not be deported. The evidence against you was strong, and you knew it. Now you face removal, and everyone tells you it would not have mattered: You would have lost at trial anyway.

That argument does not end the case. Someone with almost no chance at trial can still show that bad immigration advice harmed him, if staying in this country was what mattered most, going to trial would not have been much worse than the plea, and evidence from the time of the plea supports it. The Supreme Court called the facts unusual and said a person with no real defense will rarely be able to make this showing. So the proof is everything.

The rule comes from Lee v. United States, 582 U.S. 357 (2017), No. 16-327, decided June 23, 2017. Jae Lee asked the Court to undo his guilty plea because his lawyer had wrongly told him he would not be deported. The Court agreed that he had shown harm from that advice, reversed the Sixth Circuit and sent the case back. Chief Justice Roberts wrote for six justices. Justice Thomas dissented, joined in most of his opinion by Justice Alito, and Justice Gorsuch took no part.

Two restaurants, a plea and one wrong assurance

Lee came from South Korea in 1982, at 13. His family settled in New York, and he moved to Memphis, worked in a restaurant and then opened two of his own. In 35 years he never went back to South Korea. He stayed a lawful permanent resident and did not become a citizen.

He was also involved with illegal drugs. An informant told federal agents Lee had sold about 200 ecstasy pills and two ounces of marijuana over eight years. A search of his house turned up 88 ecstasy pills, three Valium tablets, $32,432 in cash and a loaded rifle. Lee admitted the drugs were his.

His lawyer told him trial was “very risky.” Lee told the lawyer he was not a citizen and asked repeatedly whether he would be deported. The lawyer said he would not. Lee pleaded guilty and got a year and a day in prison. His offense was an aggravated felony, which meant mandatory deportation.

At a hearing on his federal motion to cancel his conviction, filed under 28 U.S.C. § 2255, both Lee and his former lawyer testified that “deportation was the determinative issue” in accepting the plea. The lawyer called it a “bad case to try,” but acknowledged he would have advised going to trial had he known Lee would be deported. A magistrate judge recommended setting the plea aside. The district court disagreed: With overwhelming evidence of guilt, Lee would almost certainly have been convicted, with a longer sentence and deportation besides. The Sixth Circuit affirmed, reasoning that he stood to gain nothing from trial but more prison time.

The question was not whether he would have won

No one disputed that the lawyer’s advice was deficient; the government conceded it. The fight was over prejudice, meaning harm caused by the lawyer’s error, which is the second half of the test from Strickland v. Washington for ineffective lawyers.

The Court began by identifying what had been lost. Usually a defendant must show the proceeding would have come out differently. But Lee’s lawyer’s error led him to give up a trial altogether, and courts “cannot accord” a presumption of reliability to a proceeding that never took place. So, under Hill v. Lockhart, the question is whether there is a “reasonable probability that, but for counsel’s errors, he would not have pleaded guilty and would have insisted on going to trial.” That means a probability strong enough to undermine confidence in the outcome.

The Court drew a distinction the dissent rejected. If the lawyer’s mistake affected the defendant’s chances at trial, such as failing to move to suppress a confession, the defendant must show he would have been better off. Lee’s lawyer’s mistake had nothing to do with his chances. It went to his understanding of what pleading guilty would do to him. The Court said Hill itself involved this kind of error, bad advice about parole. That defendant lost because he alleged no special circumstances showing parole mattered especially to him.

Why a losing trial could still make sense

The government asked for a flat rule: A defendant with no viable defense can never show prejudice. The Court agreed that this makes sense as a general matter. A person facing long odds “will rarely be able to show prejudice” from taking a better deal.

It refused to make that a rule, for two reasons. Categorical rules fit badly with a case-by-case inquiry into all the evidence. And the question is what this defendant would have done, which may not turn only on the likely verdict. “But common sense (not to mention our precedent) recognizes that there is more to consider than simply the likelihood of success at trial.”

When the consequences of conviction after trial and by plea are similarly dire from the defendant’s point of view, even a small chance can look attractive. The Court’s example was a 20-year charge and an 18-year offer. For Lee, deportation after some time in prison was not meaningfully different from deportation after somewhat less. So, he said, he would have thrown a “Hail Mary” at trial.

The government answered with Strickland’s line that a defendant has no entitlement to “the luck of a lawless decisionmaker.” The Court said that line belongs to the presumption that completed proceedings were reliable. When the question is what a person would have decided, even a highly improbable result may matter, to the extent it would have affected the decision.

What the record had to show

This is the part of the case to read twice. Courts, the Court said, “should not upset a plea solely because of post hoc assertions from a defendant about how he would have pleaded but for his attorney’s deficiencies.” Judges “should instead look to contemporaneous evidence to substantiate a defendant’s expressed preferences.” That means evidence from the time of the plea, not only what a person says years later.

Lee had it. He had asked his lawyer about deportation again and again. Both he and the lawyer testified that he would have gone to trial had he known, and the government did not dispute that deportation was the deciding issue. And at the plea hearing, when the judge warned that a conviction “could result in your being deported” and asked whether that affected his decision, Lee said “Yes, Your Honor.” Asked how, he said “I don’t understand,” and turned to his lawyer. Only after the lawyer called it a “standard warning” did he go ahead.

His ties pointed the same way. He had lived here for nearly three decades at the time of the plea, had built two businesses and was the only family member here who could care for his elderly parents, both naturalized citizens. There was no indication he had any ties to South Korea.

The government invoked Padilla v. Kentucky’s requirement that rejecting the plea would have been rational. It argued that Lee would be deported either way and trial would only add prison time. The Court disagreed. With correct advice, Lee would have known the plea meant certain deportation. Trial meant deportation “almost certainly.” If deportation was the determinative issue, if the person had strong connections to this country and no other, and if the consequences of trial were not markedly harsher than pleading, “that ‘almost’ could make all the difference.” Against a chance of staying stood a year or two more of prison. “Not everyone in Lee’s position would make the choice to reject the plea. But we cannot say it would be irrational to do so.”

A footnote matters for anyone who heard a warning from the judge. Several courts have said such warnings can undercut a claim of prejudice. Lee’s case, the Court noted, involved a lawyer’s advice that specifically undercut the judge’s warning, which he said on the record he did not understand.

The dissent: This turns Strickland on its head

Justice Thomas would have required proof both that the defendant would have gone to trial and that he would likely have done better there. In his view Hill stated only a threshold, and the majority had created separate tests for different kinds of cases. With overwhelming evidence and no defense, he wrote, Lee would have faced the same deportation with more prison, so he was plainly better off with the plea. He warned of many challenges to old pleas, costly hearings and a rule not limited to immigration. In a part Justice Alito did not join, he also repeated his view that the Sixth Amendment does not require immigration advice at all. The majority answered that it was not removing the prejudice requirement. “The issue is how the required prejudice may be shown.” It said Frye and Lafler, on which the dissent relied, involved defendants who alleged that they would have accepted plea offers with competent advice, while Lee said he would have rejected his plea.

Where Lee leaves a person with a plea

The Court held that Lee had shown prejudice and sent the case back “for further proceedings consistent with this opinion.” With the lawyer’s error conceded, it resolved the one disputed half of the claim. Its value lies in what it permits when the lawyer’s error went to what the plea would do to the person, not to the chances at trial: A court cannot deny relief just by pointing to the strength of the evidence, and it must consider what deportation meant to this person.

Two things bear on who can use it. The government conceded the lawyer’s error here; the duty behind that concession comes from Padilla v. Kentucky, and timing limits that duty. Chaidez v. United States held that, under federal law, a person whose conviction was final before Padilla (March 31, 2010) cannot use Padilla’s rule. That case involved a lawyer who gave no advice, and a false assurance like the one Lee received can be treated differently. And the Court did not reach Lee’s separate argument that with correct advice he could have bargained for a plea without deportation.

What to gather if this happened to you

These steps are our practical advice, based on these decisions.

• Find the plea transcript. What you said when the judge warned you can be the best evidence you have, or the worst.
• Ask for your old lawyer’s file. Notes, emails and texts about immigration can show whether you asked and what you were told. In Lee, the former lawyer confirmed that deportation was the deciding issue and that he would have advised trial had he known.
• Document your ties at that time. Family here, who depended on you, work, property and how long you had lived here. Then show what ties you had, or did not have, to the other country.
• Compare the two outcomes as you saw them. How much more prison did trial really risk? Lee depended on that difference being small.
• Be honest about the alternative. Winning means losing the plea. If the charge comes back, the risk is real.
• Do not wait. Lee used a federal section 2255 motion, and other routes depend on custody and on which court convicted you. Each has its own timing rules, and a lawyer should check them promptly.

California has a separate route

California provides a separate route for a person who is no longer in criminal custody. Under Penal Code section 1473.7, a prejudicial error damaging your ability to meaningfully understand, defend against or knowingly accept a conviction’s immigration consequences can justify setting aside the conviction or sentence. You need not prove ineffective assistance of counsel. You must establish the statutory ground by a preponderance of the evidence and show that the conviction is causing, or could cause, removal or denial of an immigration benefit, lawful status or naturalization. The court may find a motion late if it was not filed with reasonable diligence after the later of the immigration notices specified in the statute. Bring those notices with the plea papers.