Supreme Court Breakfast Table

Friends:

Walter’s last post about the travel-ban litigation focuses on one of the few blockbuster issues before the court this term. But however extraordinary President Trump’s order may be, and however the court rules on it, it’s worth remembering just how draconian the ordinary course of immigration litigation can be.

We’re still awaiting the court’s decision in Jennings v. Rodriguez, which was argued in November. That case concerns the rights of noncitizens who are subject to mandatory detention while the government is seeking to deport them. The case is a class action, and the platintiffs argue that these noncitizens are entitled to bond hearings and—if the detention lasts for six months or more and detainees can show they are not a flight risk or a danger to the community—to release. The lead plaintiff—Alejandro Rodriguez—is a lawful permanent resident brought to the country as an infant. He was later convicted for possession of a controlled substance and “joyriding.” The government detained him for more than three years without a bond hearing; ultimately, his challenge to the government’s attempt to deport him succeeded, and he was released. This case is a very big deal in the immigration-law world. If the plaintiffs win, a significant number of individuals will be entitled to bond hearings. At oral argument, the court seemed deeply divided.

But two smaller cases, each involving a single litigant, are lessons in just how harsh the government’s approach to immigration has been long before—to borrow a phrase from the great constitutional scholar Charles L. Black Jr.—the Trump administration made “[t]he curves of callousness and stupidity intersect at their respective maxima.”

The first of these is a case where I helped to represent the petitioner: Esquivel-Quintana v. Sessions. (It’s worth remembering that the case was initially captioned Esquivel-Quintana v. Lynch, since it was the Obama administration that initially sought to deport our client.)

When he was 12 years old, Juan Esquivel-Quintana moved to the United States with his parents on an immigrant visa and became a lawful permanent resident. In 2009, California charged him with unlawful intercourse with a minor, alleging that he broke the law by having sex with his girlfriend beginning when she was 16 and he was 20. He pleaded no contest and was sentenced to 90 days in jail and five years’ probation

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The government then sought to deport Esquivel-Quintana. It argued not only that he should be deported, but that he should be deported for having committed an “aggravated felony.” This characterization is important, because individuals convicted of an aggravated felony are ineligible to get their deportation canceled and can never return to the United States. (Individuals convicted of other offenses have the opportunity to persuade the government to cancel their deportation.)

The government claimed that Esquivel-Quintana’s crime—entirely consensual sex with a 16-year-old—constituted the “aggravated felony” or “sexual abuse of a minor,” a crime that federal immigration law groups with “murder” and “rape.” (The language appears in 8 U.S.C. § 1101(a)(43)(A).) To get there, the government (and the Board of Immigration Appeals and the 6^th Circuit Court of Appeals) had to ignore the fact that in the overwhelming majority of states, what Equivel-Quintana did would not only not have been an aggravated felony; it would not have been a crime at all. In all but a small handful of states, the age of consent is 16.

So it was not surprising that the court, in a unanimous opinion written by Justice Thomas, rejected the government’s position. What’s surprising, and distressing, is that the government sought mandatory deportation in the first place.

And Friday, the court handed down Lee v. United States. Jae Lee moved to the United States with his parents when he was 13. His parents became citizens, but Jae remained a legal permanent resident. He never returned to South Korea.

In 2008, a government informant reported that, over the course of eight years, Lee had sold him 200 ecstasy pills and two ounces of marijuana. The government got a warrant, searched Lee’s house and found 88 pills. It charged Lee with a single count of possessing ecstasy with intent to distribute.

Lee hired a lawyer, and told the lawyer he was very worried about being deported. The lawyer told Lee that going to trial would be “very risky” and that he should accept a plea deal instead, because he would get a lighter sentence. He also told Lee that he would not be deported if he pleaded guilty.

Before a defendant can actually enter a guilty plea, the judge engages in a discussion with the defendant to make sure the defendant understands what he is doing and wants to waive all the rights that go along with a trial. In Lee’s case the judge warned him that a conviction “could result in your being deported” and asked Lee whether that would “affect your decision about whether you want to plead guilty or not.” Lee answered “Yes, Your Honor.” When the judge asked Lee to elaborate, Lee turned to his lawyer who essentially told him not to worry, because the judge was just giving a “standard warning.” So Lee pleaded guilty.

The lawyer was dead wrong. Lee had pleaded guilty to an “aggravated felony.” (And unlike Esquivel-Quintana, the crime to which Lee pleaded guilty is clearly on the list.) So he was subject to mandatory deportation with no chance ever to return to the United States.

Lee challenged his conviction, arguing that his lawyer had provided ineffective assistance, in violation of the Sixth Amendment’s guarantee of effective assistance of counsel. The Supreme Court has a two-part test for assessing ineffectiveness claims. First, a defendant must show that his lawyer’s performance fell below the acceptable range. (The Supreme Court has been distressingly willing over the years to uphold even woeful performances, but that’s a story for another day.) Second, the defendant must show that he wasprejudiced by his attorney’s failing performance: that is, that it made a difference in his case. When a defendant goes to trial, this means showing a reasonable probability that, but for his lawyer’s errors, the outcome would have been different. When a defendant pleads guilty—as Lee did—this means showing that but for the lawyer’s errors, the defendant would not have pleaded guilty and would instead have insisted on going to trial.

Even the government agreed that Lee’s lawyer failed the performance prong of the ineffectiveness inquiry. But the government argued that Lee had not been prejudiced: He would have been convicted if he had gone to trial, and he would have been deported anyway.

Chief Justice Roberts’ opinion for the court rejected the government’s position. He acknowledged that Lee was in a position with no really attractive options. But Roberts explained that even the smallest chance of success at trial may lead a defendant to reject a plea deal if the deal leads inevitably to mandatory deportation. And because Lee would have rejected the plea deal “in favor of throwing a ‘Hail Mary’ at trial”—had his lawyer given him accurate advice about the plea—he was entitled to a replay.

It’s hard to know whether that will make any difference in the end. The pills were found at Lee’s house, and the government may well be able to convict him at trial and deport him. But reading between the lines of the Chief Justice’s opinion, which mentions Lee’s success as a restaurateur (at two Chinese restaurants in Memphis) and his status as the sole family member who could take care of his elderly parents, it’s hard to escape the sense that the court recognizes just how harsh U.S. immigration law already is. And the justices don’t like it. Whether they want to give the Trump administration a green light to make things even worse remains to be seen.