Henry Montgomery will observe his 69th birthday next month. Of his three score and nine years, Montgomery will have served 52 in prison. He was 17 when he killed Louisiana deputy sheriff Charles Hurt, was convicted in state court, and was sentenced to die. He was 20 when the Louisiana Supreme Court reversed his conviction because of the atmosphere—racial hostility and even cross-burnings—in East Baton Rouge at the time of his trial. He was 23 when he was retried and when the new jury picked “guilty without capital punishment” as its verdict, which meant mandatory life without parole. He was 43 when Evan Miller was born, and 66 when, in Miller’s case, the U.S. Supreme Court held that “the Eighth Amendment forbids a sentencing scheme that mandates life in prison without possibility of parole for juvenile offenders”—meaning defendants who, like Montgomery, were underage at the time of the crime. The Court didn’t hold that such a sentence was never permitted; but the majority opinion by Justice Elena Kagan said, “we think appropriate occasions for sentencing juveniles to this harshest possible penalty will be uncommon.”

On Tuesday, the U.S. Supreme Court heard Montgomery’s argument that Miller v. Alabama should allow him the hope of parole—the bare legal possibility, if nothing else, that he may one day demonstrate that he has changed, and walk in the open air briefly before he dies. Montgomery v. Louisiana focuses on a single question: Does the Court’s decision in Miller apply to all prisoners who were sent to prison for life without parole, no matter how long ago, for crimes they committed as juveniles?

The question of “retroactivity” is an important battleground in criminal law. Say that you are in prison, convicted of a crime. You believe that some feature of your trial—the racial makeup of the jury and the selection process that produced it, say—violated the Constitution. You argued the issue in state court; when you lost there, you appealed your conviction to the state supreme court; when you lost there, you petitioned the Supreme Court for review. Without comment, the Supreme Court denied review. Your conviction and sentence are now final.

One morning you read that the Supreme Court has decided that this precise feature of the trial actually was a violation of the Constitution. Under this decision, you should clearly win.

What can you do? Your conviction has been upheld on appeal, and denied by the Court. This process—called “direct review”—is over and nothing can revive it.

But there is another process by which you can test the constitutionality of your conviction. It is called “collateral review.” As one example, a prisoner can ask a federal district court for a writ of habeas corpus—an ancient legal procedure that allows a court to review even final convictions for constitutionality.

When you were convicted, the state was following the rules as they stood. Now they have changed. Henry Montgomery got a full range of procedures as they were understood half a century ago; should he be able to reopen his case because of a case decided in 2012?

The Court faced that question in 1989 in a case called Teague v. Lane. Frank Teague, convicted of attempted murder and robbery, challenged the prosecution’s exclusion of African Americans from the jury. Teague was convicted; the Illinois Supreme Court denied his appeal; and the Supreme Court denied a petition for cert. Then he moved the case to federal district court, seeking habeas corpus. He lost in district court and appealed to the Seventh Circuit.

Then the Supreme Court decided to revisit the very issue Teague had raised, and the Court of Appeals postponed deciding Teague’s case until it could see what the high court did. In 1986, the Supreme Court decided Batson v. Kentucky, which overturned the precedent that had denied relief to Teague and announced a new, tougher standard of review of race and jury selection cases.

But the Sixth Circuit still turned Teague down. The Supreme Court then rejected his claim. His case, the Court said, was “final” before the Batson decision; he was not before the Court on “direct appeal”—that was already over—but on “collateral review.” So the Batson rule didn’t apply. Here’s the kicker: If Teague’s appeal had still been live, he would have been able to invoke the rule.

Teague went on to announce a new standard for retroactivity of cases. If a case announces a “new rule,” an opinion by Justice Sandra Day O’Connor said, the new rule will apply to all cases pending on direct review; but in most cases it will not apply to cases already final.

There are two exceptions, the Court said. First, a “new rule” will apply retroactively if it is “substantive,” meaning eliminating certain crimes (all sodomy cases, say, after Lawrence v. Texas) or protecting certain classes of people from certain punishments—as in the Court’s recent decisions that juvenile offenders and the intellectually disabled cannot be sentenced to death. The issue in Montgomery is whether the new rule against “true life” sentences for juvenile is that kind of “substantive” rule. The Miller Court said that states could no longer subject juvenile defendants to automatic sentences of life without parole; it didn’t say that a court could not sentence any juveniles to that penalty. Is that a “substantive” exclusion of juveniles—or a requirement of individualized sentencing that makes a mere “procedural” change to the law?

The second exception to Teague is for a “watershed rule of criminal procedure,” meaning one that the Court finds to be an “absolute prerequisite” to a fair and accurate trial. This is a terrific exception except that, well, there seemingly aren’t any “watershed cases.”

The Teague Court explained that restricting habeas corpus respects “the principle of finality which is essential to the operation of our criminal justice system.” The Warren Court had been enthusiastic about habeas relief for state prisoners; by the time Teague came before the Court, official attitudes toward habeas corpus had turned chilly. Seven years after Teague, Congress enacted (and Bill Clinton signed) the Antiterrorism and Effective Death Penalty Act (AEDPA), which bars federal judges from granting habeas corpus to inmates even when state courts misapplied the law—unless the state court made an “unreasonable” mistake of law or fact. Today, from the combination of Teague and AEDPA, habeas relief is out of reach for many state prisoners who might have had a chance in earlier years, and the Court’s current majority seems content with that. Legal journalist Lincoln Caplan not long ago called habeas “the withered writ”: “These reversals [of lower-court decisions granting a writ] matter because they almost always involve life-and-death stakes,” Caplan writes. “The habeas story is about capital punishment.”

There’s no doubt that many of these prisoners have committed terrible crimes, and that constant relitigation of criminal trials is draining and expensive. In the real world, every system has to decide how much leeway to give convicts to relitigate their convictions, and how much injustice to tolerate in its courts. But the current system seems, from the outside, like a version of Franz Kafka’s “Before the Law,” in which a “man from the country” seeks to enter the law but is blocked by an officious doorkeeper. The man from the country waits his whole life to enter; when he is dying, he asks the doorkeeper why in all these years no one else has used the door. “This entrance was assigned only to you,” the doorkeeper explains. “I’m going now to close it.”

The Court Tuesday spent a great deal of time talking about whether it would even decide the retroactivity question in this case; much of the argument considered whether the Court had jurisdiction. The Court may actually punt in Montgomery’s case—closing his door of the law, probably forever. But the question will be back.


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