Henry Montgomery Paved the Way for Other Juvenile Lifers to Go Free. Now 72, He May Never Get the Same Chance.

As Eric Alexander entered the Louisiana State Penitentiary, known as Angola, he found himself transported back 25 years, to a place he had never wished to revisit. “All these things that I observed upon walking into prison for the first time as a teenager, I began to experience again in there,” he said. “The smell. The sound. It reminded me of what it was like. And I guess I had never thought about it since I came home. I made it my business not to think about it.”

Alexander was arrested in 1994 for his role as a lookout in an armed robbery that killed a store owner in Memphis, Tennessee. He pleaded guilty and was released from prison after 10 years, becoming an advocate for kids living in the kinds of traumatic circumstances in which he’d grown up. In Nashville, where he lives now, Alexander mentored students in city schools, then became a program developer for the YMCA, organizing wilderness retreats in the summer. Today he’s a legislative advocate for the Washington, D.C.-based Campaign for the Fair Sentencing of Youth.

It was through the campaign that Alexander found himself at Angola on the morning of April 11. The massive complex recalled the Tennessee penitentiary where he was once incarcerated. At that time, he said, “everyone knew full well if you were black and young, you were going to serve your time in West Tennessee, whereas if you were white and young, you would be sent to a prison in East Tennessee, where there were services around computer literacy and other things.” As at Angola, a former slave plantation named after the homeland of those once forced to work there, men at the prison harvested crops on the grounds. “The only reason I escaped fieldwork was because I became a licensed barber,” Alexander said.

He had not been back inside a prison since his release. And while he was unnerved by his own visceral reaction to Angola, he was glad to be there. It was an important day: 72-year-old Henry Montgomery was up for parole.

Montgomery was the same age as Alexander had been, 17, when he was arrested for shooting a white police officer in East Baton Rouge. Montgomery’s crime took place decades before, however, in 1963 — and he was sentenced to life without parole. But more than 50 years later, Montgomery would open a path for freedom to thousands of people like himself, doomed to die in prison for crimes they committed as kids. In 2012, the U.S. Supreme Court decided a landmark case, Miller v. Alabama, which declared that such sentences, when imposed mandatorily, were unconstitutional for juvenile defendants. The ruling was based on research showing that children’s brains are not as fully developed as those of adults, making them less culpable for their actions and more capable of change. As states responded to Miller, Louisiana fought back against applying the decision retroactively. But Montgomery challenged his sentence all the way up to the Supreme Court — and in 2016 he won.

People line up outside the Supreme Court on Oct. 13, 2015, as the justices hear arguments in Montgomery v. Louisiana.

Since the rulings in Miller and Montgomery v. Louisiana, more than 500 people have been freed from prison who were once serving life without parole for crimes they committed as juveniles. Many more have been re-sentenced, among them Montgomery, who was given a parole-eligible life sentence in 2017. Of the more than 50 people released from Louisiana, several were at Angola for the hearing that day. “Some of them were gray-haired and leaning on canes,” recalled Jody Kent Lavy, executive director of the Campaign for the Fair Sentencing of Youth, who attended the hearing with Alexander. “Some of them were younger. But everybody knew Mr. Montgomery.”

Montgomery had gone before the parole board once before, in February 2018. He was rejected by a vote of 2-1. The rationale was that he had not participated in enough programs over his five decades in prison. Though Montgomery was supposed to wait two years for another chance, his lawyer successfully sought a rehearing, much to the dismay of his victim’s relatives, who had testified against him and were prepared to do so again. Nonetheless, Alexander felt optimistic. “I was excited for Mr. Montgomery. I was thinking, How could they not grant him parole after the U.S. Supreme Court had passed a mandate in his name? … But it turned out to be the total opposite.”

“I was excited for Mr. Montgomery. I was thinking, How could they not grant him parole after the U.S. Supreme Court had passed a mandate in his name?”

Unlike Alexander’s final parole hearing years ago, Montgomery went before the parole board remotely, via a TV monitor linked to its Baton Rouge office. Looking back at him on the screen was the presiding member, Brennan Kelsey, joined by two others. Kelsey, a physical therapist from Amite, Louisiana, had no background in criminal justice when he was appointed to the parole board. But he was a longtime friend of Louisiana Gov. John Bel Edwards, who hailed from the same town. The first-term Democrat won a surprise victory in the fall of 2015. “It’s hard to pin it, but there was something more about John that he had that you knew he was kind of destined for something really big,” Kelsey told a local Fox station in January 2016. Less than two weeks later, Edwards appointed Kelsey to the parole board.

“Mr. Montgomery, you said you’ve been incarcerated for how long?” Kelsey asked.

Fifty-five years, Montgomery said.

“Fifty-five years,” Kelsey repeated. “Your last write-ups were in 2013 and 2014, is that correct?”

Yes, Montgomery answered.

In fact, Montgomery had collected only 23 write-ups total during his time at Angola — a remarkable record for a near-lifetime spent behind bars. But Kelsey didn’t acknowledge this. “Tell me about the write-ups in 2013 and 2014,” he pressed.

Montgomery struggled to reply. As his lawyers showed at trial, he has quite a low IQ and a hard time expressing himself. At his 2018 hearing, his lawyer had been forced to help him along — “he’s very, very nervous this morning,” Baton Rouge attorney Keith Nordyke had explained — but there was an additional problem: Montgomery couldn’t hear. “It looks like I’ll need you to translate, Mr. Nordyke, because Mr. Montgomery is more hard of hearing than I am,” one of Kelsey’s colleagues joked. Prison staff adjusted the volume of Montgomery’s hearing aid — a box hanging from his neck that resembled a “repurposed cassette-tape player,” as one reporter described it. Nevertheless, Nordyke had to loudly repeat most of the questions for his client.

Montgomery spoke haltingly, often mumbling and trailing off. But he clearly named the first write-up from 2013: “smoking in an unauthorized area.” A deputy warden offered the second — “clothes left on his locker box,” he said. But he made clear that Montgomery was no troublemaker. “He’s not a problem to us at all.”

Some 20 minutes into the hearing, Andrew Hundley stood to speak. In his 30s, Hundley was the first “juvenile lifer” freed under Miller and Montgomery, released in June 2016. Now he’s the executive director of the New Orleans-based Louisiana Parole Project, which has helped all the state’s returning juvenile lifers find housing, employment, and support. Hundley hoped to do the same for Montgomery, reiterating what the board was told in 2018: Montgomery had a bed waiting for him at The Refinery, a faith-based mission in Opelousas, Louisiana, whose director was watching in Baton Rouge that day. “I hope this board gives Henry the same opportunity that multiple individuals have been able to take advantage of and be successful since the U.S. Supreme Court decision that bears his name.”

Three people came to oppose Montgomery’s release that day. Two were relatives of Charles Hurt, the deputy officer shot by Montgomery. By all accounts, Hurt was well-loved in the community; on the day he died, he was on patrol looking for truants and encountered Montgomery skipping school. Hurt’s daughter, Linda, was angry to be returning to testify so soon after she last spoke before the board. “You have no idea how this affects me,” she said. “How it has affected me since I was 6 years old.” Although she said she had forgiven Montgomery, she did not think he should be released.

The audio from the parole hearing stops immediately after Kelsey makes his announcement. It does not capture Montgomery’s confusion.

After a brief recess, the first two parole board members said they would vote to grant parole. But the decision had to be unanimous. “Unfortunately, Mr. Montgomery, I’m gonna have to vote to deny you parole,” Kelsey said. He repeated what the previous parole members had said in 2018: Montgomery had not participated in enough programs. “I think that’s a lack of maturity,” he said. “It’s your responsibility to continue to work hard on the inside. … Take as many programs as you can. Continue to work hard. But that’s my vote for today.”

The audio from the parole hearing stops immediately after Kelsey makes his announcement. It does not capture Montgomery’s confusion; his inability to hear exactly what Kelsey had said. “It obviously didn’t register with him what had happened,” Lavy said. “His lawyer turned to him and said, ‘Henry, you’ve been denied.’ And he just looked stunned. As we all did. Much of the room was in tears.”

Alexander had still not fully processed the hearing when we met in Nashville last month. It was not only the cruelty of telling an elderly man with cognitive challenges that he just needed to work harder to ever leave prison that left Alexander struggling for words. “I saw a lot of myself in him,” Alexander said. He was struck by Montgomery’s difficulty expressing himself, which reminded him of his own early inability to articulate the childhood trauma that had contributed to his crime. For years Alexander had craved the kind of outpouring of love and support shown to Montgomery that day. He wanted him to “finally get to see people around him hug him and cheer for him. I long for that for him because that’s something that I longed for myself.”

The entrance of the Louisiana State Penitentiary, known as Angola, on Oct. 14, 2013.

Who Is Considered Redeemable

In many ways, the plight of Henry Montgomery is hard to understand. No one has argued he poses a threat to society. Nor is there is any tangible benefit to keeping him behind bars, beyond a lingering need for retribution. Meanwhile the costs of keeping him incarcerated are clear. Montgomery is one of scores of elderly men at Angola, where the vast majority will die on the grounds. The Angolite, a prisoner-run magazine, prints regular death notices, a hospice provides end-of-life care, and multiple cemeteries provide an ever-expanding burial ground.

Should Montgomery live to see his next parole date, it is hard to imagine he will have a better shot at release. After the hearing ended, Nordyke asked the warden what other programs Montgomery might take. “The warden said, ‘Oh, there may be some substance abuse class he hasn’t taken,’” Lavy said. “He doesn’t have a substance abuse problem.” To Lavy, the truth of the matter comes down to a story that is as old as the U.S. criminal justice system. “It’s a white police officer. He is a black teenager. It’s 1963, just months before the ‘I Have a Dream’ speech.” In fact, as she points out, Montgomery was originally sentenced to die, but the sentence was overturned after the Louisiana Supreme Court found that a racist atmosphere — and the presence of the Ku Klux Klan — had infected the trial. “That’s the context in which the crime took place. There is no discussion of that. But in thinking about this outcome, you can’t ignore that history. You can’t ignore the power dynamics at play.”

The racist myth of the “teenage superpredator” convinced U.S. lawmakers and courts that kids should serve “adult time for adult crimes.”

Indeed, Montgomery’s case is not only inextricable from Louisiana’s racist past, it is emblematic of how so many other U.S. children came to be sentenced to die in prison in the years that followed. Newspapers seized on Montgomery’s nickname, “Wolf Man” (originally a reference to his oversized incisors), while the district attorney dismissed his developmental limitations. “He may have the mind of a 3-year-old, but he has the cunning of a wolf,” he said. Decades later, the racist myth of the “teenage superpredator” convinced U.S. lawmakers and courts that kids should serve “adult time for adult crimes,” fueling a wave of reforms to toughen juvenile sentencing. Among the vocal proponents of such policies were Democratic politicians like Joe Biden, who in a 1993 speech issued dire warnings about the menacing “cadre of young people, tens of thousands of them, born out of wedlock, without parents, without supervision, without any structure, without any conscience.”

It was amid this dehumanizing rhetoric that the Clinton administration passed its now infamous 1994 crime bill. Among its major impacts was banning Pell Grants that once allowed for college education in prisons — a devastating assault on the rehabilitative goals incarcerated people were expected to pursue. “Prison guards came around and confiscated everything,” Alexander recalled. “They would actually say things like, ‘Oh, you think you’re better than everybody else,’ and throw my papers in the garbage. Sometimes throw them in the toilet.” At the time, Alexander says, “it made me doubt whether or not I would be able to transition back into society, because in my mind education was the only way that I could take away the stain of incarceration.”

Today there is some political support for restoring Pell Grants to people in prison — and the crime bill has become a perennial subject of critique. Yet, despite rulings like Miller, the legacy of the tough-on-crime era remains largely untouched. Even very young children continue to be treated like adults for the purpose of prosecution. And while the U.S. Supreme Court has had several chances to abolish life without parole sentences for juveniles altogether — as 21 states and the District of Columbia have done to date — it has instead preserved the assumption that there are some “children whose crimes reflect irreparable corruption,” as Justice Anthony Kennedy wrote in Montgomery.

Crucially, Kennedy’s logic was that such youths are “rare” — rather than an impending army — and that juvenile life without parole sentences should thus be given out sparingly. With the court now poised to revisit juvenile life without parole in the notorious D.C. sniper case, however, there is real reason for advocates to worry that the door will be opened even wider for more young people to end up in Henry Montgomery’s shoes. As I wrote after the 2016 ruling, “while it may be easy to accept that, as an old man, Henry Montgomery is not the same person he was in 1963, it is difficult to imagine such sober perspective governing the fate of a 17-year-old who today committed the same crime.”

In fact, although Louisiana has made some important criminal justice reforms since Montgomery — including raising the age at which juveniles can be automatically transferred to adult court — a 2017 amicus brief before the U.S. Supreme Court by the Louisiana Center for Children’s Rights and the Juvenile Law Center argued that prosecutors continue to defy Miller and its progeny in their approach to old and new cases alike. With 258 juvenile lifers eligible for re-sentencing after Montgomery, prosecutors announced they would seek new life without parole sentences in more than 80 cases — over 30 percent and “a far cry from ‘rare’ and ‘uncommon,’” as LACCR attorney Jill Pasquarella argued. In East Baton Rouge Parish, where Montgomery is from, the district attorney was “pursuing JLWOP at a rate of 42 percent.” The vast majority of these cases involved black defendants: 75 percent according to the brief. But the numbers were even more stark when it came to new cases: of the juvenile defendants sentenced to life without parole since Miller, the brief found, 92 percent were black.

Lives like Montgomery’s end up in the hands of people who may be either clueless or indifferent when it comes to the racist history of juvenile life without parole.

On May 29, Lavy, of the Campaign for the Fair Sentencing of Youth, published an editorial on the racism at the heart of Montgomery’s case. It pointed out that on the same day Montgomery was denied parole at Angola, the board voted to free a juvenile lifer “who had served a similar amount of time, had a less stellar prison record, and was convicted of killing a black woman.” While Lavy supported that vote, she wrote, “it’s hard to shake the idea that the differing outcomes in these cases is a reflection of the value we as a society place on white versus black lives.”

Kelsey, the board member who denied Montgomery parole, did not respond to phone calls asking him to discuss his vote. But as with the parole process across the country, when it comes to deciding who is redeemed or redeemable, politics often has the final say. With board members serving at the pleasure of the governor, who comes from a long line of law enforcement and faces re-election later this year, lives like Montgomery’s end up in the hands of people who may be either clueless or indifferent when it comes to the racist history of juvenile life without parole — or places like Angola.

The last person to speak in support of Montgomery in April was New Orleans-based activist Norris Henderson. A respected leader among reform advocates, he spent almost 28 years at Angola, released in 2003. He urged the board to consider the context in which Montgomery spent his first decades at Angola. These were years when it was notorious as “the bloodiest prison in America,” he explained. The men inside were not focused on what little programs the prison had to offer. “They were concerned about basic survival.” Besides, it was simply not true that Montgomery had been lax in his efforts to get involved in activities at the prison. In the 1970s, a time when lifers were not even eligible for educational programming, Montgomery founded the Angola Amateur Boxing Association, which still exists today. “We all learned the discipline, not only for self-protection, but to deal with the environment,” Henderson said. In fact, he said, he owes his own success to such early mentorship by people like Montgomery.

To Alexander, the boxing program was emblematic not only of Montgomery’s capacity to contribute to society, but of his humanity and love for his community. “To build a program that says, ‘I’m going to ensure that I live in harmony here, that we can find a way to constructively live here in peace, without fighting and killing each other,’” he said, “I thought that should have really counted for something.”