Montgomery was found guilty and received an automatic death sentence. But his conviction was later overturned. In a two-day retrial in 1969, he was found guilty again, this time receiving a mandatory life sentence — but again without a separate sentencing hearing where he could introduce mitigating evidence.

“He may have an I.Q of 84,” Pitcher said about Montgomery, “but he has the cunning of John Dillinger. … He may have the mind of a 3-year-old, but he has the cunning of a wolf.”

Montgomery was arrested after a 16-year-old witness told police he had seen him fleeing the scene where Hurt was shot. As his trial approached, newspapers routinely referred to Montgomery as “Wolf Man.” He’d been given the nickname by family and friends because of his oversized incisors, Montgomery’s cousin told Reckdahl, but in the press it took on a more menacing air. District Attorney Sargent Pitcher, a member of the local White Citizens’ Council, sought the death penalty, telling the all-white jury that anything less would be “jeopardizing the life of every law enforcement officer in this parish.” To undermine court-appointed defense lawyers’ attempts to show that Montgomery had signs of developmental disabilities, prosecutors introduced a fingerprint card from the local jail that stated he was more than 6 feet tall and weighed 165 pounds — designed to show the truth about “this child with the little mind at the end of the table.”

Even before the high-profile crime, Louisiana was fraught with the racial strife emblematic of the South at that time. Just a few months earlier, in August 1963, Baton Rouge newspapers had taken note of the “revival of the Ku Klux Klan.” Crosses burned across the state to protest school integration. On the lawn of the state Capitol in Baton Rouge the year before, a 4-foot cross was set ablaze, with a Klan spokesperson promising more in “at least 15 to 20 southern Louisiana towns,” according to the Associated Press.

Hurt, a father of three young children, was the first police officer to be killed in East Baton Rouge in decades, according to the local press. The Baton Rouge Advocate described a “massive manhunt” involving hundreds of cops, along with “volunteer officers.” Over 28 hours, authorities blocked roads and deployed bloodhounds. “Every Negro fitting the general description of the suspect, thought to be tall and slender, was apprehended,” the Advocate reported. More than 60 black men, from 16 to 59 years old, were taken into custody. “Long as you were black, they were picking you up,” one man, now 70, who was arrested on his way to work, told New Orleans reporter Katy Reckdahl in a recent investigation revisiting the case.

HENRY MONTGOMERY had just turned 17 when he shot a sheriff’s deputy in East Baton Rouge, Louisiana. It was November 13, 1963. The police officer, Charles Hurt, was on patrol for truants in the African-American neighborhood of Scotlandville, when he found Montgomery, a 10th-grader who had skipped his third-period class to take a nap in a field near his school. Hurt “frisked” Montgomery from behind, his partner would later testify. The teenager would tell police he “panicked,” shooting Hurt dead with a stolen .22-caliber pistol.

On Tuesday, October 13, almost 52 years after the crime that sent him to prison, the U.S. Supreme Court took up the case of Henry Montgomery.

It was a chance to address unfinished business: In their 2012 ruling in Miller v. Alabama, the justices invalidated sentencing schemes like the one that condemned Montgomery to die behind bars, concluding that mandatory life without parole violates the Eighth Amendment ban on cruel and unusual punishment when imposed on juvenile defendants. As Justice Elena Kagan wrote for the 5-4 majority, “children are constitutionally different from adults for purposes of sentencing” — their brains have not developed as fully, making them less culpable for their crimes, and they have more potential for rehabilitation. What’s more, Kagan noted, in previous rulings striking down mandatory death sentences, “this Court has required sentencing authorities to consider the characteristics of a defendant and the details of his offense before sentencing him to death.” The same should be true, the Miller ruling said, for a defendant facing death in prison for a crime committed as a child.

For more than 2,000 prisoners across the country, Miller rekindled hope of a shot at freedom. There was no guarantee, however. The Court made clear that life without parole is still a valid punishment for teenagers. A person who committed a crime before 18 could still be sentenced to life without the possibility of parole, assuming a judge gave due consideration to the individual factors in the case. And there was no mandate for states to make the ruling retroactive. As juvenile lifers across different states sought resentencing hearings in the months that followed Miller, many were told that the ruling did not apply to them. Although 14 state supreme courts have ruled it is indeed retroactive, seven have not. Louisiana, is among the latter. The Montgomery case asked the Supreme Court to resolve the question once and for all.

Yet the Court on Tuesday felt far removed from the lives hanging in the balance. Most of the morning was spent not on the merits of Montgomery’s case, but on the question of whether the justices even have jurisdiction to rule on Miller’s retroactivity at all. This was particularly vexing given that both sides — along with the Obama administration — agreed that the Court is indeed authorized to decide the issue. To allow for the possibility that it is not, the justices tacked on an additional 15 minutes to oral arguments, inviting Washington lawyer Richard Bernstein, a former clerk for Justice Antonin Scalia, to convince them that they should not be hearing the case at all.

This separate but pivotal question, whose answer is wrapped in impenetrable layers of legal precedent — and rooted in historical tensions between state and federal courts — took over arguments completely. Louisiana attorney Mark Plaisance, who represents Montgomery, spent much of his time fielding challenges about jurisdiction — although he managed in his closing seconds to declare that people like his client “deserve a chance at redemption.” In one rare moment when the justices seemed to take an interest in the problem of unconstitutional confinement, Justice Stephen Breyer pointed out that “there were some people in Salem who were imprisoned for being a witch” — an admittedly “outrageous example” to make a point that could perhaps have been more effectively illustrated by the real-world example at hand: a half-century old case that predates the Kennedy assassination, is rooted in the segregated South, and involves a defendant who is poised to die in prison.

In his closing statements, Bernstein called it a “fantastic discussion,” reiterating his belief that the Court had no jurisdiction over the matter at hand.

But outside the Court, Xavier McElrath-Bey expressed frustration. He had traveled from Chicago to attend oral arguments, along with activists from the D.C.-based Campaign for the Fair Sentencing of Youth, some of whom lined up outside the Court around 6 a.m. McElrath-Bey spent 13 years in prison after being convicted of a gang-related murder when he was just 13 — he knows all too well what it is to be sentenced as an adult at a young age. But inside the Court, “the language was above my head,” he said. To the extent the justices addressed Miller’s retroactivity, the debate was over another technical question: whether the decision created a “substantive” rule — which would be applied retroactively — versus a “procedural” rule, which would not. “I understand that ‘substantive’ has a legal definition,” McElrath-Bey said. But what he considers “substantive” is what he knows to be true through his own lived experience, supported by empirical scientific data that has underwritten the Court’s decisions in the past: that teenage brains are not as fully developed as adults, that young people change and mature. “It’s hard for me to accept that the fate of these [juvenile lifers] is reliant on this legal debate,” he said.

Illinois, where McElrath-Bey is from, provides a sobering glimpse of what juvenile lifers are up against even in states that have applied Miller to pre-2012 cases.

Earlier this year, after reconsidering the case of 38-year-old Adolfo Davis, a Cook County judge nonetheless resentenced Davis to life without parole for his role in a murder committed when he was only 14. To many, the decision to reimpose a life sentence was particularly galling given that Davis himself did not carry out the killing — a reminder of how judicial discretion can lead to the most punitive results, no matter what mitigating factors might exist.

Among the states that have refused to provide access to such hearings at all are those holding the highest number of people serving life without parole for crimes they committed before they were 18. Some of these cases are decades old. In Pennsylvania, home to some 500 juvenile lifers – the highest in the country — a woman named Trina Garnett remains imprisoned for a crime committed in 1976. Garnett was just 14 when she was arrested for setting fire to a neighbor’s home in an impoverished neighborhood in Chester, Pennsylvania, killing two kids. Her sentencing judge called her case “one of the saddest I’ve ever seen” — Garnett was a victim of severe abuse and neglect from a young age; she exhibited profound mental disabilities and was in and out of homelessness. Yet Pennsylvania’s mandatory sentencing statute meant the judge was unable to exercise mercy or even consider her youth, traumatic upbringing, or her potential later in life. She was sent to adult prison at 15, where she was raped and impregnated by a guard.

I wrote about Trina Garnett in 2012, following oral arguments in Miller. When the court’s ruling came down that June, Garnett’s sister, Edy, cried happy tears over the phone at the thought that Trina would have a chance to come home and spend her remaining days with her family. But today, Garnett remains incarcerated at the State Correctional Institution at Muncy, where she relies on a wheelchair and has multiple sclerosis. She turned 54 earlier this month.

Yet Garnett is luckier than some. For a fellow SCI Muncy prisoner named Sharon Wiggins — reportedly the longest serving female lifer in Pennsylvania — even a favorable outcome in Montgomery would come too late. Though she lived to see the ruling in Miller, Wiggins died of a heart attack less than a year later.