At the age of 17, Henry Montgomery killed a Baton Rouge, Louisiana, police officer in 1963 and was sentenced to life without parole for the crime. More than 50 years later, his attorneys are trying get him from behind bars, or at least a reduced sentence, under a 2012 U.S. Supreme Court decision that said mandatory life without parole sentences for juveniles are unconstitutional. 

The ruling applies to cases after 2012, but Montgomery's attorneys said it should apply retroactively, with the idea that someone shouldn’t be in prison for something that is no longer recognized as legally sound. But Montgomery, along with thousands of other inmates facing similar sentences, may not get the parole they have wanted for so long.

The Supreme Court heard arguments Tuesday on whether states should be required to grant new sentencing hearings to prisoners who were minors when they committed their crimes. Even though the case, Montgomery v. Louisiana, seems like it could be easily won, Montgomery faces many legal battles on his way to getting the U.S. Supreme Court on his side. A 1989 Supreme Court ruling limits what cases can be looked at retroactively. What's more, the court may not have the jurisdiction to make a ruling on the case because Montgomery may have taken a shortcut to the Supreme Court, bypassing lower federal courts. The case has raised questions about whether the futures of hundreds of criminals who were sentenced as adults while underage should be reconsidered more than four years after the Supreme Court said such sentences were unconstitutional.

“We know that going forward we can’t [give a mandatory sentence to] kids for life without parole, the Supreme Court made that clear, but the argument has been ‘what about those kids who were sentenced before the 2012 decision? Mr. Montgomery is one of those. What about him?’” said Perry Moriearty, a professor at the University of Minnesota Law School who has written about retroactivity.

There are several key Supreme Court cases that could decide Montgomery's future and that of other youth offenders like him. The decision relating to mandatory life without parole sentences began with Evan Miller. In 2006, Miller was convicted of aggravated murder at the age of 14 and was sentenced to life in prison without parole in Alabama after he set his neighbor's home on fire and left him to die. Miller appealed his conviction, arguing that his life sentence was cruel and unusual. The case eventually made its way to the U.S. Supreme Court, which ruled in 2012 that life without parole sentences for juvenile homicide offenders was unconstitutional under the Eighth Amendment’s ban on cruel and unusual punishment.

Montgomery, now 69, filed an appeal in a Louisiana state trial court to have the 2012 Supreme Court ruling on mandatory life without parole sentences apply to his sentencing, but the court denied his motion. The Louisiana Supreme Court also denied Montgomery's case, citing a 1989 principal outlined in the Supreme Court case Teague v. Lane, in which Frank Teague tried to challenge the deliberate exclusion of African-Americans from the jury at his trial. Teague, who was found guilty in 1979 of attempted murder of police officers in Illinois, appealed his decision through various courts, but they rejected his claims. 

Eventually, the Supreme Court ruled in another case, Batson v. Kentucky, that a prosecutor can't exclude jurors based on race — exactly what Teague was arguing. Teague argued that the decision should apply retroactively to him. The Supreme Court said it shouldn't apply to Teague because his conviction was final before Batson v. Kentucky, but it also laid out the exemptions as to when a case can be applied retroactively, typically known as the Teague principle.

That brings us back to Montgomery. In deciding that the Miller v. Alabama ruling was only a procedural change in the law, the Louisiana state court said it shouldn’t be applied retroactively to Montgomery under the Teague precedent. That means Louisiana wouldn't recognize the 2012 Supreme Court ruling in Montgomery’s case, even though he was sentenced to mandatory life without parole when he was a only a teenager. 

“Fairness lies at the center of this particular case,” Marsha Levick, the deputy director of the Pennsylvania-based Juvenile Law Center and a member of Montgomery’s legal team, told the Supreme Court during Tuesday's arguments.

The question with retroactivity has always been where to draw the line, Moriearty said. If the courts were to reopen every single criminal conviction to see if decisions should be applied retroactively, the legal system would get too clogged up. Under the juvenile justice issue alone, there are roughly 2,000 offenders serving life sentences for crimes they committed when they were minors.

The U.S. Supreme Court drew a line with the Teague case, articulating for the first time that if a decision is considered a substantive change in the law, it can be applied to cases retroactively, but if the change is more procedural in nature, it shouldn’t be applied retroactively. A case can be applied retroactively if it is a procedural change only if that change is considered a watershed decision, said Katherine Mattes, a professor at Tulane University Law School in New Orleans who studies criminal litigation.

Defining what is substantive and what is procedural is complicated. A substantive rule places certain people or certain conduct beyond the state’s power to punish, Mattes said. 

“For example, the rule that a state may not execute juveniles, or that juveniles may not be sentenced to life without the possibility for parole in non-homicide cases, are rules that protect a particular class of persons from punishment,” Mattes said.

Procedural rules regulate the way courts determine if a person did something illegal. An example of a procedural rule, Moriearty said, would be a court deciding that a jury, not a judge, should make sentencing decisions.

“That decision, even though it’s significant, it doesn’t have that same gravity [as a substantive change],” Moriearty said. “It merely reallocates decision making authority.”

Montgomery's attorneys are arguing that the Miller case should be applied retroactively because it is a substantive change. But lawyers for Louisiana argued Miller only changed a sentencing process, making it procedural, the Hill reported

Another barrier that exists for Montgomery is whether the Supreme Court is even allowed to issue a ruling. Washington, D.C. attorney and former Justice Antonin Scalia clerk Richard Bernstein argued before the justices at their request that the court doesn’t have jurisdiction in the case.

Bernstein argued that because states have the right to decide whether they want to use the Teague principal, the Supreme Court shouldn’t second guess how states interpret the principal, Moriearty said. Bernstein also argued that the Montgomery should have his case go through lower federal courts before the U.S. Supreme Court could have jurisdiction over it.


Legal experts have said that the Montgomery case should qualify for the Teague exception because the Miller case was a substantive change in the law. Moriearty wrote an article arguing that Miller was a substantive change, and Douglas Berman, a sentencing expert and law professor at Ohio State, submitted a brief to the Supreme Court also saying the change was substantive.

These experts are not the only people who are on the side of the court granting the Montgomery case to move forward. “The idea that we were ever sending children to life without parole is barbaric,” Marjorie Esman, executive director of the Louisiana chapter of the American Civil Liberties Union, told Al Jazeera. “They are different from adults, and they have a different sense of culpability and cause and effect. We need to give them the benefit of understanding the way they develop.”