Supreme Court Dispatches

Is Life Retroactive?

He was sentenced to life without parole at 17. Fifty years later, the Supreme Court weighs setting him free.

Man behind bars.
Montgomery v. Louisiana could affect the fates of prisoners sentenced to life without parole as juveniles.


At the white-hot center of retroactivity doctrine and federal/state jurisdiction roils an oral argument that may or may not have something to do with sentencing juveniles to life without parole. This morning, during arguments in Montgomery v. Louisiana, we hear a good deal from the Supreme Court about the forced incarceration of witches and lots more about the eternal raging war between “substantive” and “process” changes to the law. Whether that will come to mean much of anything for the more than 2,000 people sentenced as juveniles to life without parole before the Supreme Court ruled that such sentences—when mandatory—violate the constitution is anybody’s guess.

Back in 2012, the high court decided in Miller v. Alabama that mandatory life-without-parole sentences for young people who committed their crimes as juveniles violate the Eighth Amendment. The court left open the possibility that life sentences could be on the table if the sentencing judge carefully considered a host of factors that took the offender’s age into account, “among them, immaturity, impetuosity, and failure to appreciate risks and consequences.” Following Miller, some state courts or legislatures opted to re-examine LWOP sentences. Fourteen state supreme courts decided to apply Miller retroactively. Seven and some federal appeals courts don’t think it looks backward.

So the issue in Montgomery is simply whether, post-Miller, every state must offer a new sentencing or parole hearing to anyone serving life for crimes they committed before age 18. Retroactivity is a bit like The Matrixall flawless internal logic that goes down easier with vodka. But before the justices can wade into the question of whether Miller can be applied retroactively, they need to decide whether they even have the authority to hear the case. Over 75 minutes, four attorneys argue those two questions, on which hang the fate of more than 1,000 juveniles.

The young person at the center of the case is Henry Montgomery, who in 1963 was a black teenager convicted for the murder of a white deputy sheriff in East Baton Rouge, Louisiana, amid a backdrop of racial strife. Montgomery was 17 at the time of the shooting. He is 69 today. He has spent the last 52 years in prison. He was sentenced to death in a trial that was so compromised by Ku Klux Klan threats that the original conviction was tossed. After a retrial, Montgomery was sentenced to mandatory life without parole. In the wake of Miller he sought to revisit that sentence, but Louisiana’s Supreme Court ruled Montgomery wasn’t entitled to a new sentencing. He’s at the court today asking whether he really has to die in prison, even though the Supreme Court has said youthful offenders should not.

But before we do battle over retroactivity, the court needs to sort out whether it can even hear the case—because if the Louisiana Supreme Court decided Montgomery’s appeal based on state law rather than federal law, the supremes might not be able to wade in. Since both parties believe the court has jurisdiction to hear this case, the court reached out and appointed Richard D. Bernstein to argue that it doesn’t.

Everyone seems to agree that this is one of those all-eyes-on-Kennedy cases. So it may or may not be important that one of Justice Anthony Kennedy’s few questions at oral argument is: “If a State says, we acknowledge that we are holding a prisoner in contravention of Federal law but we choose to do nothing about it, the State can be required under the Supremacy Clause, under its own procedures, to enforce the Federal law?”

Justice Stephen Breyer asks a hypothetical question about masses of Americans incarcerated under a sedition law the Supreme Court then finds unconstitutional. Doesn’t the court have jurisdiction to hear the case when “there are human beings who are in prison, who are there without having violated any valid law, because it was always protected by the First Amendment?” Or, as he rephrases the question: “I mean, why doesn’t it violate the Constitution to hold a person in prison for 20 years, for conduct which the Constitution forbids making criminal?” When Bernstein evades the hypothetical, Breyer changes it up, now proposing that the masses of people unconstitutionally rotting in prison were charged with being witches. In Massachusetts. Before that was found to violate the constitution. In 1820.

Mark Plaisance, representing Montgomery, gets 15 minutes to explain that the high court should hear the case and also resentence his client. He tangles with Justices Antonin Scalia and Samuel Alito, who don’t think the court should hear this case at all. All of his time goes to the technical, jurisdictional question; then Deputy Solicitor General Michael Dreeben gets 15 more minutes to contend that the court should hear the case and is well into his own presentation before Chief Justice John Roberts gently nudges him to maybe discuss the retroactivity question, meant to be the heart of the case.

So here’s where things could get crazy, until they don’t. In order to determine whether a decision applies retroactively (most don’t, in part because of society’s interest in the finality of convictions), the courts try to decide whether the big new case has announced a substantive new rule of law or merely a procedural rule. Substantive rules can be found retroactive. Dreeben contends Miller announced a substantive rule because it “goes far beyond merely regulating the procedure by which youths are sentenced for homicide crimes and compelled the State to adopt new substantive sentencing options.”

When pressed to say why Miller should be applied retroactively, Dreeben says the “Court made very clear that it believed that of the 2,000 people that were in prison and under mandatory life for juvenile homicide, the Court believed that that penalty was frequently disproportionate … and that it was not a sentence that was consistent in most cases with the mitigating characteristics of youth.” Dreeben contends that the jurisdictions that have allowed resentencing of youthful offenders saw a big decrease in the time they needed to serve. To which Alito replies, “Would it be accurate to say that a rule is substantive if it makes a particular outcome less likely or much less likely or much, much less likely than was previously the case?”

The last advocate on parade this morning is Kyle Duncan, who ably represents the state of Louisiana despite the fact that he is—on more than one occasion—wholly unable to get a word in edgewise. Because he is contending that the court has jurisdiction to decide the case, he must first get past Scalia, who balks when Duncan says that “as a practical matter, this court ought to weigh in.” Scalia replies tartly, “We weigh in when we have jurisdiction. You don’t think that matters at all?” adding, “What you said doesn’t make much sense.”

Duncan replies: “I think it makes sense.” Scalia is puzzled: “Let’s get in there quickly, whether we have jurisdiction or not?”

Justice Elena Kagan goes after Duncan repeatedly with the procedural-versus-substantive stick, and Breyer tests out the idea that Miller announced a “watershed” rule, which might also provide an exception to the general preference not to make rulings retroactive. But in general, the enthusiasm for not hearing this case seems to outweigh the enthusiasm for deciding it, and we may be looking at another appeal—there are more cases in the pipeline—before the question of whether life sentences without parole for juvenile defendants can be contested by septuagenarians.

Henry Montgomery has lived an exemplary life behind bars, proving that a young life looked at retroactively may militate against life without possibility of parole. That we may not be able to look at that retroactively is too ironic to contemplate.