Last month marked two years since the U.S. Supreme Court ruled in favor of Henry Montgomery, a quiet prisoner at the Louisiana State Penitentiary at Angola.

Montgomery was 17 when he killed Deputy Charles Hurt in Baton Rouge in 1963. A teen with a low IQ and oversized incisors that earned him the nickname “Wolf Man,” Montgomery did poorly in school and was playing hooky that day, taking a nap in a grassy area of a park when Hurt, a plainclothes sheriff’s deputy, found him while trying to clear truants from that area.

Read the original special report:Louisiana man, imprisoned for 50 years for killing a deputy, is at center of Supreme Court hearing on youth sentencing

Though his lawyer claimed he was not guilty because of insanity — what his lawyers described as “the mentality of a 3-year-old” — Montgomery was convicted of first-degree murder. First he got the death penalty. Then, after a new trial and conviction, he was, in accordance with state law, automatically sentenced to life without parole.

But in 2016, the high court read the pleadings of Henry Montgomery and ruled that a “meaningful opportunity to obtain release” should be given to prisoners like him who were serving time for crimes they had committed as juveniles.

On Monday, Montgomery was given that chance and was formally denied parole by a three-person panel.

The decision raises the question of what a “meaningful opportunity” is for prisoners like Montgomery, said Perry Moriearty, who co-directs the Child Advocacy and Juvenile Justice Clinic at the University of Minnesota. “Part of the problem is that this is uncharted territory,” she said. “Parole boards across the country are struggling with how to review the sentences of adults who were incarcerated decades earlier for offenses they committed as children.”

Because Louisiana’s powerful law enforcement organizations had submitted letters pushing for a denial, some also saw the decision as an indication that the parole board couldn’t look beyond Montgomery’s crime.

“It’s the one thing he can’t change,” said lawyer Carol Kolinchak, who consults on juvenile cases in Louisiana and trains lawyers working on such cases. “And the Supreme Court knew that he had killed a sheriff’s deputy when they decided this case.”

In 2016, in the case Montgomery v. Louisiana, the Supreme Court found that mandatory life-without-parole sentences were unconstitutional for Montgomery and other prisoners who had been convicted of crimes they committed as juveniles. Only the rare, incorrigible person would likely be deserving of such a sentence, the court found.

“Parole boards across the country are struggling with how to review the sentences of adults who were incarcerated decades earlier for offenses they committed as children.”—Perry Moriearty, Child Advocacy and Juvenile Justice Clinic

“The penological justifications for life without parole collapse in light of the ‘distinctive attributes of youth,’” Justice Anthony Kennedy wrote in the Montgomery decision. It outlined the science about still-developing adolescent brains, which causes adolescents to be impulsive but also gives them capacity for change.

Defense lawyers knew that from the outset that, in many ways, it would be an uphill battle to resentence these cases and move people toward parole, Kolinchak said. “Every one of these is a murder. Every one of these is horrible. In every one of these, there are loved ones that won’t come back,” she said.

Still, since the decision, about half of the 2,600 inmates nationwide are no longer serving life without parole for crimes they committed as juveniles, according to the Campaign for Fair Sentencing of Youth. Some have been released, and the rest have been resentenced to something other than JLWOP.

Montgomery gets a hearing

Montgomery, now 71, also seemed to be moving toward freedom. He was resentenced last year by a judge who called him a “model prisoner.” He made his way onto the docket of the Louisiana Board of Pardons & Parole on Monday.

The board heard how Montgomery has been a role model and a coach for decades and how he helped form a boxing team at Angola, according to reports from the hearing’s observers and from press accounts written by the Associated Press and The Baton Rouge Advocate.

“In my opinion, Henry Montgomery will become a productive member of society, if allowed a second chance.”—Alvin Roche Jr., one of three members of the parole board

Board members also heard how he was active in his church, how he’d worked in the prison’s silkscreen shop for 20 years and was named employee of the month eight times. He had not earned a GED, but he had earned a waiver for that because of his borderline IQ, which is in the low 70s. Though he’s taken only two classes, they weren’t offered at Angola until about 20 years ago and he was considered ineligible for any that require reading and writing, advocates said.

He was denied, in a 2-1 vote, by parole board members who questioned the number of classes he’d taken, asked about his role in the murder a half-century ago and noted that his release was opposed by Hurt’s family, the East Baton Rouge Parish Sheriff’s Office and the Louisiana Sheriffs’ Association.

Access to letters the Department of Corrections sent for Montgomery’s hearing was denied under a parole board regulation that precludes the release of anything submitted by a private entity on behalf of a victim.

“One of the rules of law is that you don’t kill somebody, and when you do, there’s consequences.”—James Kuhn, one of three members of the parole board

Parole board member Alvin Roche Jr., the designated victims’ advocate, was the only vote for Montgomery. “In my opinion, Henry Montgomery will become a productive member of society, if allowed a second chance,” Roche said.

Montgomery needed a unanimous decision. James Kuhn, a retired appellate judge, cast one of two opposing votes.

“One of the things that society demands, and police officers certainly demand, is that everyone abide by the rule of law. One of the rules of law is that you don’t kill somebody, and when you do, there’s consequences,” Kuhn said during the hearing.

As board chair, Kuhn is designated as the person who can publicly comment on cases; he did not return phone calls for this story.

Looking differently at juvenile cases

Defense attorneys and experts who work on juvenile cases said the parole board somehow looked past the Supreme Court’s directive that “children who commit even heinous crimes are capable of change.”

They pointed to the hearing itself, which did not focus on whether Montgomery was the rare prisoner who could not be released, as the Supreme Court had described.

“Nothing was presented to show that he was incorrigible. The argument about not taking enough education courses seems to be a fig leaf,” said lawyer George Kendall. He directs the Squire Sanders Public Service Initiative, which has worked pro bono on a number of juvenile cases across the country, though not Montgomery’s.

Instead, the parole board should have focused on something very different, given its charge by the Supreme Court, he said. “This individual committed this crime at a very young age, when, as we know now, the most important parts of his brain were not fully developed. So the question is: How did he turn out when nature was done with him?”

Moriearty agreed. “In the case of a juvenile who’s served 54 years of an unconstitutional mandatory life-without-parole sentence, Montgomery says that you should begin with the presumption that he’s not permanently incorrigible and therefore eligible for release. The state can try to rebut it,” she said.

Certainly, determinations of rehabilitation can be more complicated for people more recently convicted, Kendall said. “But these old guys, we can look at their records. We don’t have to guess at all.”

“This individual committed this crime at a very young age, when, as we know now, the most important parts of his brain were not fully developed. So the question is: How did he turn out when nature was done with him?”—George Kendall, Squire Sanders Public Service Initiative

Until Monday, hopes were high that Montgomery might also be able to earn parole after 54 years of incarceration, since he hadn’t had a disciplinary write-up for years and had been given a very low risk-assessment score, clocking in with a negative-one score in the Louisiana Risk Needs Assessment, or LaRNA.

Still, those hopes had been tempered by the reality that Montgomery is seen as a cop-killer, as a person who gunned down a sheriff’s deputy who had three young kids. “That was always going to be the problem with this case,” Kendall said.

Similar hurdles around the country

It’s a tough hurdle to overcome, one not isolated to Louisiana or to people who were juveniles when they committed their crimes. In New York last year, Supreme Court Justice Maria Rosa issued a contempt order against the state’s parole board over the case of John MacKenzie, an exemplary prisoner who was an adult when he shot an officer in 1975 and has been denied parole repeatedly. Rosa found that the board’s decision gave undue weight to the crime of conviction instead of MacKenzie’s rehabilitation.

Beyond that, what a highly publicized case like Montgomery’s makes clear is that the Supreme Court’s instructions about “a meaningful opportunity” are being interpreted through parole procedures that differ broadly from state to state. For instance, some states allow defendants to appear in person. Montgomery, who is hard of hearing and has trouble understanding complicated questions, was connected to the procedures by video and was clearly confused during the process, observers said.

Guidelines about these cases published in May by the Louisiana Board of Pardons and Parole noted that “juveniles are constitutionally different from adults” and instructed the parole panel to “give great weight to the fact that youth are less responsible than adults are for their actions.”

To understand the barriers that Montgomery defendants face, Sarah French Russell, a professor at Quinnipiac University of Law in Connecticut, sent a survey to 49 states with parole boards and received answers from 45 of them.

“It is difficult for someone to focus on remorse for a terrible act while at the same time cataloging one’s accomplishments.”—Sarah French Russell, Quinnipiac University of Law

“State parole boards have traditionally had great flexibility in terms of the criteria that they use in making release decisions,” she wrote in a report, “and they have not been required to provide a realistic opportunity for release to prisoners.” That’s particularly true if the defendant’s offense was violent, she noted.

But Russell’s analysis of the U.S. Supreme Court directives on the matter notes that a 2010 decision, Graham v. Florida, requires that states “give defendants like Graham some meaningful opportunity to obtain release based on demonstrated maturity and rehabilitation.” She believes that “a releasing authority that relies too heavily on the severity of the initial offense in denying release will run afoul of the Eighth Amendment.”

Yet, Russell also acknowledges what observers saw at Montgomery’s hearing — that juveniles who have been incarcerated since their teen years likely had limited education, didn’t have opportunities to develop communication skills, and may have difficulty refuting information that’s kept in private, parole-board folders.

By their very nature, hearings like Montgomery’s are meant to convey conflicting information, Russell wrote. Parole board members want to hear about genuine remorse but also understand how the crime was affected by the defendant being a juvenile, all during a short time period.

“It is difficult for someone to focus on remorse for a terrible act while at the same time cataloging one’s accomplishments,” Russell wrote. “And it is extremely hard for a person to express remorse and responsibility for the crime at the same time as he or she suggests mitigation regarding an offense.”

The May directive to the Louisiana Board of Pardons and Parole notes, in one sentence, the importance of its role. “The availability of a meaningful opportunity for release on parole is what makes the juvenile’s life sentence constitutionally proportionate,” it reads.

This story was written for the Juvenile Justice Information Exchange, a national news site that covers the issue daily.