Last September, a group of academics and activists gathered at Princeton University to discuss the limits of artificial intelligence in public policy.

The longest debate concerned some of the most sensitive decisions in the justice system, like whether to release a person on bail or parole. Many in attendance were queasy about using algorithms to determine prison stays — not least because crime data tends to reflect racial bias. But one conference goer in particular stood out for his skepticism.

His name was Bruce Reilly. The deputy director of a New Orleans organization called VOTE, which advocates for the formerly incarcerated, Mr. Reilly is a minor celebrity in the field. He was a sounding board for the leader of the recent Florida ballot campaign that restored voting rights to up to 1.4 million former felons, and helped lead similar initiatives in Rhode Island and Louisiana.

Mr. Reilly, 45, has playful eyes, weathered skin and a boyish voice, and at Princeton, he wore a dark blazer that did not appear to be his natural uniform. Though it was barely midmorning, his shirt was already threatening to decamp from his pants as he turned to address a Princeton postdoctoral researcher sitting next to him.

“Statistically,” Mr. Reilly told her, “the safest person to let out of prison is a murderer.” The academic, Madelyn Sanfilippo, screwed up her face in apparent disbelief.

“You seem like a person who cares about statistics,” Mr. Reilly continued, arguing that people convicted of lesser crimes often cycle in and out of prison, while someone serving a long sentence for murder has typically matured out of crime by the time he is released.

“That makes sense,” Ms. Sanfilippo said, warming to the claim.

They talked amiably for a few more minutes. When they were done, Mr. Reilly turned and whispered in my ear: “She has no idea.”

‘You need to be broken’

In September 1992, a Rhode Island community college professor named Charles Russell picked up a 19-year-old hitchhiker on an interstate. The two men eventually made it to Mr. Russell’s home, where they smoked marijuana and talked books for hours.

About a week later, the hitchhiker returned. The two men talked and smoked again. But as Mr. Russell performed oral sex on him, the younger man became enraged. He picked up a knife and began stabbing at Mr. Russell’s neck.

Mr. Russell tried to defend himself with a fireplace poker, but the man wrested it from his hand and beat him until he stopped moving. As the younger man was dressing, Mr. Russell rose to his feet, picked up a small statue and charged. The man took the statue away and delivered several more blows, fatally crushing Mr. Russell’s skull.

A year later, acting on a tip, the police arrested Bruce Reilly. He confessed that he had snapped during the sexual encounter, and that the fight had escalated once Mr. Russell fought back.

“I was reacting — I had stuff built up inside of me,” Mr. Reilly told me. Facing life in prison, he accepted a deal to plead guilty to second-degree murder, and a judge sentenced him to 20 years, followed by 25 years of probation.

Many of Mr. Reilly’s high school friends were shocked, if not entirely surprised. He had always been precocious, but his home life was a mess — his mother was in and out of psychiatric institutions, and he lived in foster care for years as a young child. As a teenager, he dealt drugs and stole license plates. He was accepted to college but didn’t fill out the paperwork in time to qualify for financial aid. He was constantly hustling from one dead-end gig or sketchy apartment to another, until one night he ended up at the home of the man he would kill.

In prison, Mr. Reilly became something of an ascetic. He read and wrote for hours each day and strictly limited his TV intake. He accumulated a small circle of friends who believed he had special insight into surviving incarceration. They would write essays on a chosen topic, like whether democracy was the best form of government, and circulate them for feedback.

When they debated prison reform, their views were a mix of Old Testament justice and New. They came to believe that their dreary sentences were central to their rehabilitation.

“You need to be broken,” Greg Tovmasian, a member of the group, told me. “You need to be completely honest with yourself about why you’re in there. If you’re constantly on the phone, talking to people out there, your head is still in society.” The flip side, they believed, was that if a person had done his grappling and come through it, there ceased to be a point to keeping him locked up.

Mr. Reilly was often the most effective legal adviser his fellow inmates ever consulted. He spent hundreds of hours studying case law in the prison library and wrote dozens of petitions, briefs and motions. He helped at least two fellow prisoners reduce their sentences by several years. “It was like magic to people — like mixing chemicals,” said his friend Steven Parkhurst, who is still in prison.

Mr. Reilly was paroled in 2005. He enrolled at Rhode Island College, worked low-wage jobs and became active in a local civil rights group that’s now known as OpenDoors. The organization was campaigning for a ballot initiative to restore the voting rights of felons after their release, and Mr. Reilly eventually worked as a strategist and volunteer coordinator for the effort, which passed.

To help continue his work on behalf of the formerly incarcerated, Mr. Reilly applied to law school. Although he scored in the top 7 percent on the standardized entrance exam, he didn’t have a bachelor’s degree, and only one of more than two dozen schools accepted him. In the fall of 2011, Mr. Reilly arrived on the campus of Tulane University — and almost immediately confronted the question that still dogs him today.

The purest test of mainstreaming

The political consensus for bringing former convicts back into society’s mainstream has shifted faster this decade than at any other moment in modern history. Late last year, President Trump signed into law a watershed bill reducing prison sentences for a range of federal offenders, with backing from a coalition that ranged from the American Civil Liberties Union to the Koch brothers. Numerous cities and states have enacted “ban the box” laws, preventing employers from asking about criminal history on a job application. The Florida initiative whose leader Mr. Reilly counseled passed by a nearly two-to-one ratio.

But many of these recent gains have accrued to nonviolent offenders. What about rehabilitation for those who have committed a brutal crime?

“We as a culture have yet to confront forgiveness for someone who commits a crime that we universally agree” is abhorrent, Mr. Reilly once told me, using an expletive. “The drug offender — that person should not even be in jail,” he continued. “The hard questions are reintegration for people the criminal justice system was actually designed for.” People like him.

Since I started tracking his career, in 2013, I’ve come to think of Mr. Reilly, whom prosecutors once described as a manipulative “predator,” as the purest test of America’s commitment to mainstreaming ex-felons. Even as Mr. Reilly makes it his life’s work to advance the cause, he finds himself illustrating its limits. That’s both because his crime was so severe and because he is not satisfied merely to be housed or employed. He craves elite credentials and recognition, like advanced degrees and fellowships, and wants to work on cutting-edge legal issues.

Last summer, I attended a Soros Justice Fellowships conference in New Orleans with Mr. Reilly, who had been invited to appear on a panel about solitary confinement. Funded by the liberal billionaire George Soros, the organization behind the conference is one of the country’s largest financial backers of criminal justice reform.

As he collected his name tag from a table, Mr. Reilly glanced down at the other names and began identifying who had won various fellowships, grants and accolades. “I’ve applied to them all, have not gotten any of them,” he said. And then, referring to his efforts in Louisiana and Rhode Island, he added with a degree of pride: “But apparently you don’t need a fellowship to win voting rights.”

When Mr. Reilly got to Tulane Law School in 2011, he initially fell in with a circle of students interested in civil rights and unfazed by his past. “He straight-up told me he had been convicted of murder,” one classmate, Allyson Page, recalled. “I was like, ‘O.K., that’s cool.’ I wasn’t expecting that, but I didn’t care that much.”

But within a few weeks, another student began to broadcast Mr. Reilly’s criminal record across campus. Some classmates complained that his presence compromised their safety and would make it harder for them to land jobs.

The story — ex-murderer at exclusive law school! — was picked up by the popular legal blog Above the Law. An unnamed student wondered if, “when placed in one of the most stress-inducing environments in the United States, Mr. Reilly will reach his tipping point and live up to his violent past.” Another espoused a form of Nimby-ism: “I think felons should get a second chance. But why at Tulane? What are we, the law school for murderers?”

TV crews turned up near his house. A producer for “Dr. Phil” called Mr. Reilly on his cellphone; a reporter from “Inside Edition” staked out his apartment.

Publicly, David Meyer, the law school’s dean, was statesmanlike. Tulane’s admissions process “allows for the possibility of redemption even in exceptional circumstances of tragedy and hardship,” he told Above the Law. But privately, Mr. Meyer seemed as panicked as anyone. Susan Krinsky, the dean of admissions, said in an interview that Mr. Meyer had told her, “You have endangered this entire community.” (Ms. Krinsky left Tulane about a year later, and Mr. Meyer declined to comment.)

Mr. Reilly, fearing Tulane would revoke his admission, tried to lie low. But he soon realized he had to stop his classmates from getting their information secondhand, off the internet. And he tried to convince his peers, one at a time, that he belonged.

“Bruce was in the hallway — he was friends with people who were conservative, people who were liberals,” recalled Tony Viviani, a close friend. “One of the most staunch conservative guys was an Alabama grad. He was talking football with him, smacking right back.”

Two years later, when I was in New Orleans to give a talk, I arranged to meet Mr. Reilly for coffee. I was fascinated by how someone could live in two completely different worlds, one familiar to me, the other unimaginable. But as the appointment got closer, I started to worry. I had a daughter, a wife. Was it really such a good idea to schmooze with a murderer?

When we did meet, we chatted for nearly an hour about writing and fatherhood. (Mr. Reilly has a daughter from a relationship in Rhode Island.) He was humble and thoughtful, and I was immediately embarrassed by the vague scenarios I had played out in my head.

Still, to this day, I sometimes struggle to shake my mental image of his crime. And I can’t help thinking: If Mr. Reilly worked at, say, a top-shelf law firm, how many partners would claim the office next to his? Bunk with him on a corporate retreat? Introduce him to their spouse and children?

Although Mr. Reilly apologized to the Russell family at his sentencing hearing in 1996, it takes only a little probing to affirm how fresh his crime remains. His victim’s sister-in-law, Marilyn Rodriguez, told me that she and her two children had been especially close to Mr. Russell, and that his death had “made a mess of our whole family.”

“The hurt is still in our family,” she added. “It can’t be undone.”

Confined by his past

Mr. Reilly, who graduated from Tulane in 2014, would like to be able to practice law, but it’s highly unlikely that he could pass the “character and fitness” portion of the bar admissions process. He’s interested in data and internet privacy issues, but he’s hard-pressed to get a foothold in such fields.

After getting his law degree, Mr. Reilly searched unsuccessfully for a position that would suit his qualifications: policy jobs in Washington, entertainment-law gigs in Los Angeles, even a job with the Tribeca Film Institute in New York. He landed only two interviews and struggled to discuss his criminal record with prospective employers.

“Once you let the debate go there,” Mr. Reilly said, “now they’re visualizing you killing someone.”

Finally, after nearly six months piling credit card debt on top of his student loans, he landed a job in New Orleans as a paralegal at the Capital Appeals Project, which represents indigent people on death row. From there he moved to another criminal justice reform organization and eventually to VOTE.

Last summer, Mr. Reilly was part of a small team of activists that met with Roger Goodell, the commissioner of the National Football League, and executives for the New Orleans Saints. He briefly told his story, explaining how he was an impulsive teenager before committing his crime, but came out of prison an adult. He made a plea for the Saints and the league to throw their weight behind initiatives that would ease assimilation. The executives nodded sympathetically.

Mr. Reilly makes a quick impression with his intellect. When he was a law student, for example, it took him only a few hours of research to conclude that Louisiana’s ban on voting by felons on probation or parole probably violated the state’s Constitution, and a large group of legal scholars agreed. Still, the fact that Mr. Reilly has devoted his professional life to the rights of the formerly incarcerated — as opposed to a less personal issue like genetically modified foods, another law school interest — testifies to the way his past confines him.

In some ways, he confines himself. Mr. Reilly has a habit of leaning into stereotypes about felons, almost as a political protest, and I sometimes wonder if it is self-defeating. The T-shirts he favors do little to conceal his tattoos, and he leans heavily on jailhouse idiom when he speaks. There are frequent allusions to “bids” (tours in prison), “guys in the yard” (fellow prisoners) and “shankings” (stabbings with a makeshift weapon).

Race also complicates his upward trajectory in an uncomfortable way. After Mr. Reilly introduced me as a journalist to fellow reformers at the Soros conference, some responded with a measure of irritation: Criminal justice issues disproportionately affect minorities, and I was going to profile a white guy? From Rhode Island? Who went to a fancy law school?

Mr. Reilly is the first to concede the advantages he has over former inmates who are black or Latino. “I can go incognito as a white guy,” he said. But he is still pained by the skepticism his race sometimes provokes among progressives.

Then there is the continuing threat to his freedom, in which even a seemingly minor political dispute can escalate into a crisis.

In December, a judicial oversight committee in New Orleans ruled that a candidate for a local judgeship had made false statements about Mr. Reilly’s employer, VOTE. On the day of the ruling, the candidate, Marie Williams, applied for a temporary restraining order against Mr. Reilly, saying he had harassed her through social media, filed baseless claims against her and endorsed her opponent.

The temporary order was granted — Louisiana has a low threshold for such actions — and a judge found probable cause to believe that Mr. Reilly violated the order when his lawyer reached out to Ms. Williams to request that she withdraw it. Now a pending warrant for his arrest could send him to jail. Mr. Reilly’s lawyer hopes to resolve the matter this month, when a court will consider the case.

The sheer hysteria of a murder conviction

Mr. Reilly is encouraged by the growing number of formerly incarcerated people who have gained entree into elite professions and rarefied social strata. He cites with pride his friend Andres Idarraga, who spent time in prison for selling drugs and later earned a law degree from Yale and worked for the famed law firm Boies Schiller Flexner; and Reginald Dwayne Betts, an acclaimed poet who graduated from Yale Law after serving time for a carjacking. Neither of them, though, has a murder conviction.

A vanishingly small number of such people have even begun to claw their way toward mainstream respectability after serving their sentences. Michelle Jones, who published original historical research while serving more than 20 years for the murder of her young son, lost out on a place in a Harvard Ph.D. program when the school overruled its own history department. (She gained admission to New York University.)

Mr. Reilly’s prison friend Greg Tovmasian, who was convicted of second-degree murder, abandoned his application to the University of Rhode Island when he was told that he would have to meet with a university official to be considered. “I just wasn’t ready emotionally to face another parole board,” Mr. Tovmasian said. Instead he earned an economics degree at the smaller Rhode Island College.

Mr. Reilly believes that by telling his story, he can help diminish the sheer hysteria a murder conviction can inspire. But while he has been granted more audiences from the likes of Princeton and the New Orleans Saints, Mr. Reilly has not found that organizations outside the criminal justice field are rushing to work alongside him, in close quarters, for sustained periods. They see him as a source of information or a helpful perspective, but rarely as a potential colleague or friend.

At the Princeton A.I. conference, Mr. Reilly had a long and seemingly productive conversation about life after prison with a man named Chuck Howell, who had an impressive job at a company that manages federal research and development centers. But later, as the two men bantered about police departments and the issue of disciplining rogue cops, Mr. Reilly spun out an extended prison metaphor.

If a gang member wrongs an inmate from a different gang, he said, leaders from the offender’s group will typically agree to punish him on their own. From where I stood, Mr. Howell, who had seemed engaged and receptive at the beginning of the exchange, started to look uncomfortable.

“The problem with the cops is they don’t do it,” Mr. Reilly continued, meaning that police departments don’t rein in rogue officers. “If you were a real gang, you’d off that guy. I’m not saying off that guy — but take care of it.”

Mr. Howell went quiet. The conversation was never the same again.

Jack Begg, Kitty Bennett and Doris Burke contributed research. Karen Ziner contributed reporting.

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