Prepping for Parole – The New Yorker

Earlier this year, the Parole Preparation Project put out a call for volunteers, and more than a hundred people applied. Many were law students and lawyers, but there was also a Planet Fitness employee, a pediatric I.C.U. nurse, a professor of philosophy, a software engineer, a waiter, and a translator. Parole Prep invited them to an orientation, and, one Wednesday evening last April, some eighty people assembled in a lecture hall at New York University School of Law. Most were in their twenties or thirties. Three-quarters were female. A few people carried reusable water bottles; one older woman walked in with a cane.

Michelle Lewin, who is thirty-two years old and the executive director of Parole Prep, stood at the front of the room, wearing a loose-fitting brown dress and worn work boots. She explained that Parole Prep requires an eight-to-twelve-month commitment. Each volunteer is assigned to a team of two or three people, then matched up with someone who has been incarcerated for decades, whom the team helps prepare for an upcoming interview before the parole board. Lewin talked about Parole Prep’s “values as a project.” “Nobody should be judged by the worst thing they’ve ever done,” she said. Then she introduced two men, Kevin Bartley and Anthony Dixon, whom she called “my uncles and my dear friends.”

Bartley, a sixty-seven-year-old man with a shaved head and a confident demeanor, spoke first. “I’m not a law student, like some of y’all,” he said. “But I am an expert on corrections. What makes me an expert? I did thirty-seven years. I came home nine months ago. I went in at twenty-eight, came out at sixty-five. I was denied parole twelve times.” He talked about his experience with Parole Prep. “I had two of the best volunteers. They were extraordinary,” he said. “I think I would still be inside if not for Parole Prep. This would’ve been my thirty-eighth year.”

The official mission of New York’s parole board is to “ensure public safety by granting parole when appropriate.” When incarcerated people appear before the board, its members evaluate “their ultimate fitness to be paroled.” The incarcerated people are expected to speak openly about their crimes, take responsibility for them, and express remorse. But some people who are convicted of very serious crimes minimize their actions when they appear before the board, saying things like “The gun went off” or “I made a mistake.” “That’s a bad thing for anyone to say,” Bartley told the would-be volunteers. Killing another man is not a “mistake.” “A mistake is you wake up in the morning and put on a white sock and a black sock,” he said. He added, “The hardest thing that you’re going to have to do if you become a volunteer is you sit down with the guys and you have to pull it out of them. It’s like pulling teeth, especially when someone carries a lot of guilt and shame, like myself.”

Dixon, a soft-spoken fifty-eight-year-old man with square-framed glasses, spent thirty-two years in prison. Speaking about the first time he went before the parole board, he said, “I failed, and I failed miserably. My particular problem was I knew what to say but I had a hard time saying it myself.” In the months before his third parole-board hearing, a team of volunteers had come to see him on weekdays, weekends, and holidays. He said that they prepared him well for the parole interview: “I felt so much confidence.” He added, “I didn’t want to let my volunteers down. I wanted to give the best presentation that I could, because I felt they had connected with me so much that it would hurt them if I was denied parole.” The board voted to release him.

New York’s state prisons hold some forty-six thousand people. Almost twenty per cent are “lifers,” which means that they are serving a prison sentence with “life” on the back, like twenty years to life. Parole Prep works only with lifers, most of whom have been convicted of murder or other acts of extreme violence. Once they have completed their minimum sentence, they are given a date to appear before a panel of usually three parole-board members. According to the Vera Institute for Justice, the success rate for lifers appearing before the board in the past three years has been thirty-six per cent. According to Lewin, the rate for people going before the board after assistance from a team of Parole Prep volunteers is about sixty per cent.

In the past five years, Parole Prep volunteers have helped a hundred and forty-nine people get out of prison, twelve of them women. Often, the relationships between the men and women in prison and their volunteers endure after the prisoners are released. Tyler Morse, who recently finished a master’s degree in women’s and gender studies at the CUNY Graduate Center, went to a Super Bowl party hosted by a man she helped get out of prison. Ben Seegars, who was released from prison in January, was a guest at the wedding of one of his volunteers, Stacy Auer. When Chloé Truong-Jones, a Ph.D. student at N.Y.U., discovered that the seventy-one-year-old man she had worked to get freed was in a homeless shelter that was unsafe, she arranged for him to stay at her boyfriend’s apartment in Bushwick while he waited for a transfer.

Recently, Gina Lee recalled the first Parole Prep meeting she attended, in the fall of 2017. A friend had been a volunteer and told her about the project; Lee was then twenty-five and working at a nonprofit that helped teen-agers who had been jailed on Rikers Island. She filled out an application, went to an orientation, and found herself on a team with another friend, John White, a twenty-five-year-old who worked for an art-auction Web site, and Olivia Button, a twenty-four-year-old manager at a software company. Lewin assigned the group to work with a sixty-six-year-old man incarcerated at Auburn, a maximum-security prison in Cayuga County, two hundred and fifty miles from Brooklyn, where they all lived.

His name was Richard Lloyd Dennis, and he had been in prison for forty-six years. The volunteers knew little more than that he had been convicted in 1972 of killing a police officer in Brownsville, Brooklyn. He was twenty when he committed the crime. At the time, anyone convicted of killing a police officer in New York State faced the possibility of the death penalty, but he was sentenced to twenty-five years to life. The parole board had turned him down eleven times.

Lee, White, and Button travelled to Auburn for the first time in December of 2017. Waiting in the prison visiting room, they noticed a short, balding man walking toward them. He looked, as Lee put it, like somebody’s grandfather. It was Dennis. All the formerly incarcerated men whom Lee had heard share their stories at Parole Prep meetings had been powerful public speakers. But Dennis rarely smiled, and he had a stutter. When the volunteers tried to broach the subject of his crime with him, he stopped talking altogether. Two hours into their interview, he said, “O.K., now you leave.” On the ride back to New York City, the volunteers were caught in a blizzard. The nerve-racking weather matched the mood in the car. Lee, in particular, was worried about the task they had taken on. “I just remember being, like, Oh, this is going to be really hard,” she said.

Today, New York’s parole board receives almost no scrutiny, but in the early seventies its operations drew enormous attention. In September, 1971, men incarcerated at Attica seized control of parts of the prison, sparking a rebellion that lasted four days. By the end of it, forty-three people were dead—thirty-two incarcerated men and eleven state workers. Afterward, an official state investigation into the uprising revealed that the way the parole board operated had been “a primary source of tension and bitterness” inside Attica. “The decisions of the parole board are fraught with the appearance of arbitrariness,” the report stated. “Even when parole is granted, inmates must often wait in prison for months while searching for jobs and places to live. This is done through the mail, and they are given little assistance.” Many of the incarcerated men also believed that the board was racially biased. Most of its members were white men; none was younger than fifty-nine.

After the rebellion, a disparate group of prominent New Yorkers formed the Citizens’ Inquiry on Parole and Criminal Justice. Ramsey Clark, who had served as Attorney General under President Lyndon B. Johnson, chaired the inquiry; the committee members included the playwright Arthur Miller, the civil-rights leader Bayard Rustin, the psychologist and educator Kenneth B. Clark, and the labor leader Moe Foner. In 1975, they published a two-hundred-page report, declaring that New York’s parole system had “failed dramatically” and was “beyond reform.” The board’s decision-making process, which was “based on an assessment of an inmate’s rehabilitation,” rested on “faulty theory,” the report said. “Since the theory of rehabilitation includes vague and subjective notions of moral character and future conduct, there is no way that the parole board can measure the degree of an inmate’s rehabilitation.” As a result, the board’s decisions about how long to keep someone in prison were “irrational and cruel.” The group shared a version of the report with parole officials before publication, but they received no response. David Rudenstine, who directed the inquiry, wrote in the final report, “It is regrettable that the primary loyalty of public officials responsible for an important social system such as parole seems to be the maintenance of things as they are.”

In the decades that followed, allegations of racism in the parole system continued to circulate. In 2016, three reporters at the Times examined thousands of decisions made by New York’s parole board and found that black men were “at a marked disadvantage.” Michelle Lewin, in the years since she started working with incarcerated people seeking parole, has come to many of the same conclusions that the Citizens’ Inquiry did, forty-four years ago. As she put it in a 2017 law-review article that she co-wrote, “The Board’s practices exemplify nationwide criminal justice policies that are rooted in retribution and racism and result in extreme punishment.”

Lewin grew up in Atlanta. Her paternal grandparents were Holocaust survivors, and she attended a Jewish day school. She told me that she did not have any non-Jewish friends until she was fifteen, after she started attending a private, progressive high school. As a sophomore at Sarah Lawrence College, she enrolled in a class called The Penal State, and the professor took a group of students to Sing Sing. “I remember just the towering cells, stacked on top of each other, floor after floor after floor,” she told me. “It was horrifying.” After college, she worked for a victims’-services group; she had a desk at a police precinct in Coney Island and accompanied officers when they visited domestic-violence victims. She later worked as a court advocate at the Hall of Justice in the Bronx, trying to persuade judges not to imprison people accused of low-level felonies.

In the fall of 2013, she enrolled at CUNY School of Law, and soon afterward she attended a meeting of the National Lawyers Guild’s Mass Incarceration Committee, in Harlem. One of the other attendees, Scott Paltrowitz, a Harvard Law graduate who worked for a prison-reform organization, had recently visited Otisville Correctional Facility, in Orange County, New York, where he had met members of its Lifers & Long Termers Organization. Paltrowitz informed Lewin and the other meeting attendees that there was a man at Otisville named Roberto Pascal, who had been in prison for thirty-three years and needed help obtaining parole. Lewin and Nora Carroll, a Legal Aid attorney, said that they would try to assist him.

Inside Otisville, Pascal gave crocheting classes to the other men, and, Lewin learned, he liked to feed Snickers bars to the groundhogs in the yard. Lewin and Carroll started visiting him every other month. They worked with him to prepare for his next parole interview, helping him draft a personal statement and studying transcripts from his earlier interviews to figure out what had gone wrong. Pascal had a heavy accent, and, in Lewin’s view, the parole board “just didn’t give a shit about him.” He seemed to appreciate the women’s efforts on his behalf, and on one visit he left them a gift of two crocheted string bikinis to pick up on their way out. (The next time Lewin sent him a letter, she told him, “Socks would’ve been nicer,” but, she says, “it was harmless.”) The parole board turned Pascal down at his next hearing, but the women continued to work with him, and he was later released.

Otisville had a very active Lifers & Long Termers Organization. While Lewin and Carroll were working on Pascal’s case, they began hearing from the group’s leaders, who told them stories about men who had been repeatedly denied parole. When the women called lawyers who worked on prison issues to get advice about how to help the men, they realized that the lawyers’ knowledge was, as Lewin put it, “really minimal.” “They really didn’t have a sense of how to actually prepare someone for the board,” she said. “Most of their clients were not getting out.”

In the spring of 2014, the two women decided to expand their efforts, recruiting volunteers and calling themselves the Parole Preparation Project. That June, at their first training session, some thirty people showed up, most of them law students. “I don’t even think they knew what parole was,” Lewin told me. “I think they just wanted to connect with people in prison.” A jailhouse lawyer at Otisville had sent them a list of men who needed help obtaining parole, and they assigned volunteers to work with several of them. Six months later, after they announced their second volunteer training, a hundred and thirty people responded, including a bartender, a retired biology teacher, and a woman who described herself as a “queer mama of twins in the pursuit of justice.”

Carroll recalled that, as word of the project spread throughout the state’s prisons, “letters just started coming.” Soon they were overwhelmed with requests from incarcerated men. In 2016, Lewin graduated from law school and began running Parole Prep full time, working out of a café in Brooklyn. The organization now has two desks at a shared workspace in Manhattan’s Chinatown. The second desk belongs to Anthony Dixon, who left prison three years ago and sometimes wears a suit to work. Parole Prep often collaborates with the RAPP Campaign—short for Release Aging People in Prison—which pushes for parole reform and has three desks nearby. A bulletin board above Lewin’s desk is covered with photographs of middle-aged and elderly men (and one woman). She explained that they were people with whom she had worked in the past five years and who had died either in prison or shortly after they were released.

One afternoon this past spring, over lunch at a soup-dumpling restaurant near the office, Lewin reflected on Parole Prep’s evolution. When the project started, she said, she thought that the work was going to be “very technical.” The first training sessions focussed on how to assemble a packet for the parole board, containing an advocacy letter and letters from relatives. “It was very legalistic,” Lewin said of the approach, “but it was not related actually at all to the work we were doing, somehow.” That work was building relationships, trying to befriend someone who had been imprisoned for decades, helping him to speak honestly about his crime. Parole Prep has attracted many volunteers with degrees from colleges such as Brown and Yale. “They come in with a lot of ideas about their politics,” Lewin told me, “but don’t necessarily have a lot of experience connecting with people in prison.”

In the past few years, she, Carroll, and another friend, with the help of several men at Otisville, have written numerous memos for volunteers on topics such as what to bring on a prison visit (singles and quarters for the vending machine), how to act when they get a collect call (don’t say anything critical of prison staff, because all calls are recorded), and how to relate to the incarcerated people they are working with (“the best advocate is someone who listens actively, hears the nuances in what the other person is saying”). They teach the volunteers how to obtain court documents in order to learn the official narrative of the crime. There are monthly meetings, too, for which Lewin brings in speakers who have served decades in prison.

Lee, White, and Button studied Parole Prep’s training materials and took notes at its meetings. From their first visit, they had only five months to help Richard Lloyd Dennis—whom they call Lloyd—prepare for his next parole interview. Volunteers working with people in prisons closer to New York City, such as Sing Sing and Fishkill, were able to visit often, but since Auburn was so far away, they had to rely more on letters and calls. In a letter to Dennis in March, 2018, a few months after they first visited him, they wrote, “With your next parole hearing quickly approaching, there is much work to do, and an important part of this work is the process of writing and reflecting.” Parole Prep had distributed a memo with writing prompts, and the volunteers began including a few of them in each letter they sent. At first, the questions were innocuous: “How would you describe yourself as a young man?” “How do you think you’ve changed since being in prison?” But soon they became more challenging: “What happened that night?” “What do you remember of the victim?” In his letters, Dennis began to tackle their questions. “Temper is an attitude, a disposition and over the years I have learned to control it,” he wrote. “I felt real bad about my situation . . . but you should know that I felt real hurt inside also for the officer and his family.”

Many people who have been in prison for thirty or forty years lose contact with their families, but, in an early letter, Dennis enclosed phone numbers for eight relatives. One Saturday in February of 2018, the volunteers got together at a coffee shop in Brooklyn to work on his parole packet. Button called Dennis’s sister, Velma, in Virginia. Velma, who had been sending letters to the parole board for years, asking for her brother to be freed, was delighted to hear that someone was trying to help him get out. Dennis was the sixth of seven siblings who had grown up in New Castle, Pennsylvania. After high school, he spent a year in the Marine Corps, then moved to New York City, where he got a job as a cook at a nursing home in Queens. Button asked Velma to write another letter on his behalf, and she sent it the following week. She wrote, “Richard has been in prison almost forty-six years now (he turned twenty-one in prison), no previous criminal record, high school graduate, employed prior to entering the system, raised in a two parent home, has four brothers and one sister (none in the system), and all of us ready to step in and help upon his release!”

By many standards, Dennis was a strong candidate for parole. He’d had no disciplinary infractions for several years; he had a place to live, with Velma; and he had lined up a job as a laborer with a contracting company run by Velma’s son-in-law. The volunteers made the drive to Auburn in February and again in April, 2018, when they conducted a mock parole interview with Dennis in the visiting room. They had studied the transcripts of his last two interviews, and had noticed that many of his answers were very short. “Just saying yes or no unfortunately paints a picture of someone who really doesn’t want to be there,” White explained. They tried to teach him a strategy that any good job interviewee knows: the art of the pivot. White told Dennis, “Even if they are asking yes-or-no questions, take every opportunity to be, like, ‘Yes, and . . .’ ” He recommended that Dennis then mention something positive, like the fact that he had many relatives willing to take him in.

In May, two weeks before the parole interview, White mailed copies of Dennis’s packet to a parole coördinator at the prison. It was fifty-seven pages long and included a well-written five-page letter from the Parole Prep team advocating for his release (“We write to voice our enthusiastic support for Richard Lloyd Dennis . . .”). The letter reminded the board how young Dennis had been at the time of the crime and cited a Justice Department report showing that “young people between ages 14 and 25 are still developing their abilities to control impulses, suppress aggression, consider the impact of their behavior on others.” The packet also included a copy of his high-school diploma, from 1969; Velma’s letter and three other letters from relatives; and three “inmate progress reports” from his boss, the prison’s librarian, who had deemed him “excellent” in categories such as “dependability” and “attitude toward authority figures.”

Inside Auburn prison, on the second floor of the Administration Building, there is a small room that is empty most of the time. With the exception of a large screen with a camera mounted above it, and an air-conditioner propped in a window—one of the few A.C. units in the entire institution—the room has the feel of a forgotten place. There are stains on its pea-green carpet, a curtain missing from one of its windows, and, when I visited not long ago, a broken replica of the state seal, on the floor. Every month, men in prison greens sit on wooden benches in the corridor outside the room and wait, sometimes for hours, for their names to be called. In the past, parole interviews were conducted in person, but a few years ago the parole board stopped coming to Auburn. The interviews are now conducted in this room via video hookup.

New York State currently has sixteen parole-board members, who conduct some twelve thousand parole interviews a year. The governor appoints the board’s members, and the State Senate confirms them. The current chairwoman is a former prosecutor, and past parole-board members have often had backgrounds in law enforcement. The job, which has a six-year term, carries a title (commissioner) and pays a salary of a hundred and twenty thousand dollars a year. The work can be gruelling. Every Monday, parole-board members drive to cities such as Syracuse, Rochester, and Buffalo, where they stay for two or three nights. Parole coördinators deliver the paper files of the incarcerated people from the prisons where they are held to the parole offices where the commissioners conduct their interviews. Carol Shapiro, who joined the board in 2017 and quit in 2019, said, “The irony is we’re travelling around the state for videoconferencing. It’s insane.”

Parole-board members conduct interviews on Tuesdays and Wednesdays and sometimes on Thursdays. In 1994, the State Legislature amended the law in order to allow victims to give in-person testimony to the parole board. On Fridays, the commissioners take turns receiving the family members of crime victims and listening to their stories. Many families bring photos and tell personal anecdotes about their loved ones. “They are very difficult sessions,” Shapiro said. “It definitely takes a toll on you—absorbing this pain over and over.” The relatives’ words are typed up into a “victim impact statement,” which is placed in the parole file of the imprisoned individual. If a murder victim was a police officer, members of the police union, the Police Benevolent Association, often accompany the family to show their support.

Parole-board hearings can run from a few minutes to an hour or more. Shapiro told me that there was very little time to read through each file. “Commissioners get the case the day they see the person,” she said. On busy days, while the lead commissioner asks the questions, the other two commissioners might review the file of the next interviewee or write a decision for the preceding one. Sometimes the multitasking can lead to a commissioner asking a question that another commissioner has asked a few minutes earlier. “There is a numbing repetition of the interview process,” Shapiro told me. “There is a witching hour. By six o’clock, you’ve kind of had it. Your head hurts, your back hurts, and you’ve heard a gazillion stories.”

In a three-person parole panel, two votes are needed for an individual to be released. Parole commissioners are supposed to follow a series of statutes—to take into account factors including an individual’s institutional record, his release plans, and the seriousness of the offense. But some board members have higher release rates than others, and everyone seems to have a different idea about how much weight to give the various pieces of information in each case. “For some, the offense is it, no matter what,” Shapiro said. “For some, it’s the victim impact [statement]. Everyone has their own values and draws different lines in the sand.”

Robert Dennison, who was appointed to the parole board by Governor George Pataki, in 2000, went on to serve as the board’s chairman from 2004 to 2007. “We’re supposed to measure remorse, but it’s kind of hard to do that,” he told me. “So you try to see if they’re really sorry for what they did, or if they just think they’re a victim being caught up in the system, or they just want to tell you what they think you want to hear. It’s certainly not a science. It’s very subjective, and sometimes we make mistakes. But, from my experience, the longer the person’s been in, the better the parole risk they’re going to be when they get out. If someone has been in for a long period of time, usually they got a terrible taste in their mouth of what prison is like, and they don’t want to do anything to put themselves back in prison.”

The people who have been imprisoned the longest, however, tend to have been convicted of the most heinous crimes, and, for parole commissioners, there is little downside to denying them parole. Although the cost of imprisonment is higher in New York than in any other state—seventy thousand dollars a year per person, and often considerably more if the individual is elderly or ill—parole-board members are not required to justify the financial impact of their decisions. The board determines not only who will be set free but what rules they must follow on the outside. Everyone who is released on parole has to report regularly to a parole officer and obey certain restrictions—such as meeting a curfew and submitting to regular drug tests—and those who do not follow the rules risk being sent back to prison. (The number of people incarcerated for such “technical violations” of their parole is higher in New York than in all other states but one, and these individuals make up nearly thirty per cent of all the people sent to New York’s state prisons each year. In 2018, the Justice Lab at Columbia University released a report, titled “Less Is More in New York,” which became the blueprint for a bill that was introduced in the State Legislature earlier this year; the bill proposes limiting the kinds of parole violations that could be punished with incarceration.)

One’s odds of being released are heavily influenced by where one is imprisoned. “State paroling systems vary so much that it is almost impossible to compare them,” Jorge Renaud, an analyst at the Prison Policy Initiative, a think tank, wrote in a report earlier this year. But Renaud’s report tried to do just that, giving each state a grade. Renaud gave his highest grade, a B-minus, to Wyoming, noting that, among other strengths, the state holds “in-person, face-to-face parole hearings,” “allows incarcerated people access to the information the Board will use to determine whether to grant or deny parole, and allows incarcerated individuals to question the accuracy of that information,” and “allows staff from the prison—who have true day-to-day perspective on an individual’s character and growth—to provide in-person testimony.” Thirty-six states got an F or an F-minus. Some of them do not allow incarcerated people to appear before a parole board at all; in others, such as Georgia, some individuals can be made to wait up to eight years after being turned down by the board before their cases are reviewed again. New York received a D-minus.

A few years ago, advocates lobbied Governor Andrew Cuomo to appoint commissioners with different types of backgrounds, which is how Shapiro, who is trained as a social worker, won a seat. She described the culture of the parole board as “very risk-averse.” At times, she recalled, she would advocate for an individual to be released, and a fellow board member would respond, “He’s playing you, Carol. He’s got your number.” Shapiro told me, “I felt like a lot of my colleagues focussed way too much on the severity of the crime. If this is your fifth, sixth, seventh, eighth, ninth parole-board hearing, we really shouldn’t be focussing on the crime anymore. We should really be focussing on your plans to go home.” She went on, “I think the purpose of parole right now is very murky. If the goal is to determine if someone is ready to go home, that’s very different than relying on: Did they serve enough time? Did the punishment fit the crime?”

The most closely watched parole hearings are those in which the individual being interviewed has been convicted of killing a police officer. “Generally, if you’re a parole-board commissioner, it’s very hard for you to let somebody out who killed a police officer, because that’s one of the things that governors do not like,” Dennison said. “The chances of that parole-board commissioner being reappointed certainly went down several notches.” In 2018, Shapiro was one of two board members who voted to release Herman Bell, the former Black Panther who had been convicted of killing two N.Y.P.D. officers in 1971. The decision was criticized by the governor, the police commissioner, the editorial boards of the Daily News and the Post, and Mayor Bill de Blasio, who urged the parole board’s chairwoman to reconsider. (“Murdering a police officer in cold blood is a crime beyond the frontiers of rehabilitation or redemption,” he wrote.) Shapiro said that she received a death threat on Facebook, and many angry letters. A few months later, the State Senate held a hearing on parole policies. James B. Ferguson, Jr., a former prosecutor who served on the parole board from 2005 to 2018, testified. Speaking about people imprisoned for very serious crimes, he said, “The inmate can be the perfect inmate. They’ve done everything they possibly can. They perhaps even demonstrate a genuinely changed person.” But sometimes “enough time has not been done,” he said. “What is the public going to say if you release Charles Manson?”

I met Dennis for the first time this past spring, in the visiting room at Auburn. By then, he had served nearly forty-eight years in prison—close to double his minimum sentence of twenty-five years. Despite his volunteers’ dogged efforts, the board had turned him down after his parole interview in May, 2018. Part of the problem seemed to be the gruesome nature of his crime. On July 24, 1971, at around 2:15 a.m., he was standing outside a bodega in Brownsville when a police officer named Robert Denton went inside to buy cigarettes, and after Denton walked out of the store Dennis cut him in the neck with a knife. “Cop Slashed to Death, Youth Seized,” the Daily News headline read. Denton, who was twenty-six, was the eighth city police officer that year to be killed on the job.

At the time, Dennis had been staying with the family of his brother Melvin’s girlfriend in Brownsville. He had no criminal record, and reporters seemed at a loss to explain why he might have killed a police officer; the News referred to the crime as “an apparently motiveless stab-killing.” The court record suggests that alcohol may have been a factor; Dennis had been drinking beer and vodka in the hours preceding the assault. His trial was held in the spring of 1972. Denton’s partner testified that Dennis had approached their patrol car shortly before the incident and asked how he could become a police officer—a detail that Dennis’s lawyer disputed but which the local press had seized upon in its reporting. Trial testimony revealed that, after Denton was stabbed, police officers who had come to the scene had beaten Dennis so badly that, at the precinct later, he had bruises on his face and body and was bleeding from both ears. He had been taken to the hospital—for a “possible skull fracture,” according to law-enforcement notes—and when Melvin arrived he found him in a wheelchair in a hallway. “I didn’t recognize him at all,” Melvin testified. “His nose was smashed and his face was about three times the size.”

By May, 2018, Dennis had been imprisoned longer than all but nine other men in New York State. If he had been convicted of killing anyone but a police officer, he likely would have been set free long ago. The reason for this may have to do, at least in part, with the power of the Police Benevolent Association. One of its mantras is “No parole for cop killers”; on the P.B.A.’s Web site, the union keeps a list of people who are in prison for the murder of a police officer, and the site promises that, if someone clicks on a victim’s name, a letter will be sent to the parole board, urging it to deny parole. Dennis’s name was on the list. Last March, the Daily News revealed that the link on the union’s Web site had not worked for five years. In late April, Patrick J. Lynch, the union’s president, held a press conference, in Albany, accompanied by widows of N.Y.P.D. officers who had been killed. The P.B.A. had brought three hundred and sixty cardboard boxes, which they claimed held some eight hundred thousand letters to the parole board, signed by supporters. “An attack on a police officer is an attack on the laws we uphold and the public we have sworn to protect,” Lynch said recently, in an e-mail. “Every time a cop-killer is released, it sends criminals a signal that there are really no laws worth following, because our justice system is unwilling to protect those who enforce them.”

Robert Denton’s best friend was Ronald Bellistri, who grew up with Denton, in Levittown, and joined the N.Y.P.D. with him, in 1969. Bellistri told me that he and Denton had attended grammar school and high school together; that Denton’s first car was a 1957 Oldsmobile; that Denton was drafted into the Army after high school and ended up at Fort Lee, in Virginia, for two years. Bellistri had encouraged Denton to join him in the Thirteenth Precinct, in Manhattan, but Denton wanted to stay at the Seventy-third Precinct, in Brownsville. “He said, ‘I love the action,’ ” Bellistri recalled. Sometimes they would run into each other when extra officers were called in to work at Vietnam War demonstrations. Bellistri said that Denton had recently married “the love of his life” and, two weeks before his death, he had bought a used Corvette, which he drove over to Bellistri’s house, beeping the horn in the driveway to show it off.

Every year on July 24th, Bellistri sends flowers to the Seventy-third Precinct, and he stops in during roll call to speak to the officers about his friend. “I don’t want them to forget him,” he told me. Over the years, Denton’s friends and former colleagues have contributed remembrances to the Web site NYPD Angels, which honors members of the force who were killed in the line of duty, going back to the mid-eighteen-hundreds. Earlier this year, Bellistri wrote on the site, “BOBBY, NOT ONE DAY GOES BY THAT I DO NOT THINK OF YOU.” Four months later, he wrote, “THIS JULY 18TH THRU 20TH IS OUR LEVITTOWN MEMORIAL HS REUNION. YOU WILL BE MISSED MY BROTHER.” This year, Bellistri, now seventy-three years old, made flyers, which he distributed at the Seventy-third and other precincts, urging people to go to the parole board’s Web site and send a letter opposing Dennis’s release at his next hearing. The top of the flyer read “URGENT” and identified Dennis as “Bob Denton’s murderer.” Bellistri said about Dennis, “He deserves to stay incarcerated for the rest of his life for what he did to Bobby.”

In the visiting room at Auburn, Dennis told me that during his decades in custody he had been confined in almost every maximum-security prison in the state; his current stay at Auburn, he said, was his third there. Auburn Correctional Facility, which opened in 1817, is one of the oldest operating prisons in the United States. The city of Auburn grew up around the prison; today, there is a Tex-Mex restaurant next door and a Hilton Garden Inn down the street. From the windows in the prison’s visiting room, incarcerated men can see townspeople strolling by, but, when I visited, Dennis had no interest in peering out the windows. “It puts me in a bad mood,” he said. “It makes me feel alone.”

One of his strategies for holding on to his sanity had been to make certain that he always had a job. Over the years, he had stocked shelves in the commissary at Auburn; helped cook the food at Comstock; mowed the grass at Attica; worked early mornings baking bread at Green Haven. From 2000 to 2008, he had toiled in the laundry at Elmira, helping clean the uniforms of other incarcerated men. (“Inmate Dennis is the laundry’s #1 machine operator, he is an excellent worker,” his boss wrote in 2006.) Besides his work ethic, Dennis was known for his intense exercise regimen: running endless laps barefoot around the prison yard, lifting weights, doing hundreds of pullups and pushups. He also meditated and practiced yoga in his cell. His volunteers had told me that he was so strong and fit that he could do pushups on only his thumbs. When I mentioned this during our meeting, a guard who happened to be passing by asked if I wanted to see his pushups—“It’s incredible,” he said—and Dennis seemed to appreciate a chance to show off his strength. In front of a vending machine in an adjoining room, away from the other visitors, he placed his thumbs on the linoleum floor, stretched out his legs, did a few pushups, and swore he could do many more.

Back at our table, we settled once again into plastic bucket chairs. His next interview was set for August, 2019, and he sounded pessimistic about his odds. “If you killed a cop, you ain’t got no hope,” he said. He was tired of the whole ritual: “You go to the board, they sit up there and smile at you. They crack jokes. You go back to your cell, and they hit you for two more years.” The last time, however, they had hit him with only fifteen months. “Everyone says it’s a good sign,” he said, “but it’s not a good sign to me.”

Yet he seemed buoyed by the commitment of his volunteers. In the eight years prior to their first visit, he had had only one other visit, from his brother Melvin and his wife. The first time he met the volunteers, he admitted, he had been uncertain of their intent. They looked “mad young,” he told me. “I said to myself, ‘What is this? Is this going to be a playground thing? Something for them to bide their time until they get something better?’ ” But they had earned his trust, coming to see him three times in four months, and, after the board denied him parole in May of 2018, they had agreed to continue working with him to prepare for his next hearing. He called them all regularly, catching one or the other on the phone every few days. “What surprised me about them was their sincerity,” he said. “I trust very few people if I trust anyone at all. They have a real naturalness.”

In the months since they had started working with him, he had tried to connect with each of them. He knew that Olivia Button liked to box, so he gave her advice on how to train and sent pages with exercises to do. When he learned that Gina Lee’s parents were from South Korea, he wanted to hear more; he’d always been interested in Korea. He discovered that John White liked yoga, too, and talked to him about yoga techniques. When the volunteers told him how they got to Auburn—leaving New York City at 4 a.m. in a rental car, driving ten or twelve hours round trip—he assumed that they must be getting paid for their work. They told him that they were volunteers. But every few months he would ask again, as if he could not quite believe that they were helping him without pay. He had little to give them in return, except for his advice on working out and healthy eating. When Lee was sick, he suggested that she try chewing on garlic. When Button’s birthday came, he mailed her two birthday cards. In his letters to them, he had expressed his gratitude. “Thanks again for all the help you are giving a person such as me,” he wrote, three months after they met. “I have not been a happy or hopeful person in a very long time.”

There is no official mechanism to require people confined in New York’s prisons to confront their guilt, to grapple with questions of remorse and responsibility, to think about how they might make amends to a victim’s family. At times, the legal system even seems to work against these goals; at trial, defense attorneys typically downplay the defendant’s culpability—or deny his guilt altogether—in an effort to minimize his punishment. Often, a defendant, long after he is convicted, will cling to the narrative of his crime that his lawyer told in court. The imprisoned individual may go years, even decades, without ever speaking honestly about his crime. The state prison system did start an “apology letter bank,” so that incarcerated people could write to their victims, but most people in prison do not know that it exists.

The most successful programs to help people reckon with their crimes have often been started by incarcerated or formerly incarcerated people. In the mid-two-thousands, José Saldaña and two of his peers at Shawangunk prison launched A Challenge to Change, an eighteen-week workshop, led by incarcerated men, which was later expanded to other prisons. “We wanted a program where a guy would come in and confront what he did,” Saldaña, who was released in 2018 and is now the director of the RAPP Campaign, told me. “We wanted total honesty.” Saldaña described the group sessions as “more difficult than we imagined” and “at times very, very emotional.” Among the program’s objectives is to counter the notion, common among people in prison, that there is a hierarchy of crimes; individuals who committed sex offenses were considered to be at the very bottom. “The murderer thinks he’s better than the rapist,” Saldaña said. “We dispelled all that stuff.”

Kathy Boudin, who was imprisoned at Bedford Hills, a maximum-security prison, for two decades, told me that most of the women with whom she was confined did not speak honestly and openly about their crimes, “because there is no safe place inside the prison system where people have a chance to do this.” In the visiting room, they often lied to their children out of a sense of shame about what they had done, but the truth inevitably became harder to conceal. “You’re in prison for eighteen years, and you’re, like, ‘I didn’t do it. I didn’t do it,’ and your children read on the Internet and they know you did it,” she said. When Boudin was released, in 2003, she had an idea to start a program that would “help people examine their lives and come to terms with what they did” and to “deal deeply with the harm” they had caused. She hoped that the program would “allow them to be able to talk to their children about it, to talk to their families about it, to not feel like they’re living in total shame all the time.”

The program that Boudin envisioned became the Longtermers Responsibility Project, which, for the past decade, has been run by the Osborne Association—a nonprofit group that works with incarcerated people and their families—at Sing Sing and Fishkill. In the program, twelve people convicted of murder-related crimes meet with a facilitator for weekly group sessions over four months. Laura Roan, a program manager at Osborne, facilitates some of the sessions. “ ‘Oh, I never meant to hurt anybody.’ That’s the story I hear over and over,” Roan said. “Well, why did you load the gun, then?” She continued, “It’s very hard to live with that idea that you are somebody who is really able to take the life of somebody else.” Perhaps this is why, as she found, many long-termers do not seem to have a coherent narrative of their own crimes. “You tell everybody something different,” she said. “You tell yourself one story, you tell your prison peers a different story.” But, Roan went on, “the parole board is asking them to tell a different story they’ve never told before. Your goal is to show them you’re safe to release.”

The stories that imprisoned men and women tell the board about their crimes often diverge from the facts in their court or parole files. Sometimes people are minimizing their guilt. Sometimes they are misremembering details of events that occurred decades earlier. Sometimes they are actually correct, and the details in the official documents are wrong. And sometimes they have no memory at all of the crime they have committed and have created a narrative about it that makes sense to them. Like many of the men with whom Dennis was imprisoned, he had repeatedly filed appeals in the courts in the first decade of his incarceration. The lawyers who wrote them argued that he had been wrongly convicted—his defense attorney at trial claimed that he was not guilty—and after he lost his initial appeals and started representing himself, writing his own legal papers and filing them pro se, Dennis continued to make this claim. His court battles continued for more than ten years. But, once he was eligible for parole, he took the advice of peers: “As long as you deny the crime, they’re going to keep hitting you.” He appeared before the parole board for the first time in the summer of 1996, when he was forty-five years old. In a room at Attica, seated across from two male commissioners, he admitted to having killed Patrolman Denton, and recounted a story about arguing with him, saying that “the argument initiated into a fight, and one thing led to another, and that’s when the officer got hit in the neck.” The parole board turned him down, writing in its decision that Dennis was “still in denial” and “does not voice any remorse.”

During the next two decades, Dennis appeared before the parole board every other year. Transcripts from his hearings show that he attempted to express remorse. In 2002, he said, “I take responsibility for everything I did. I’ve hurt a lot of people through this.” In 2010, he said, “I regret it. Wasn’t my intention to murder anybody or kill anybody.” In 2011, the state parole board began using a new “risk assessment” tool, to measure the likelihood that an individual would commit another crime once he was released. An assessment of Dennis found that he was a low risk, but the board continued to turn him down. In the course of twelve parole appearances, he was interviewed by twenty-five board members, some of them more than once. In 2018, the parole board explained its decision with the same language it had used many times before: “Your release at this time is incompatible with the welfare of society.” There was no indication of what he could do to increase his odds of obtaining parole the next time.

When I first met Dennis’s volunteers, last March, they were just about to go back to Auburn for the first time in ten months, to start getting him ready for his parole hearing in August. On March 30th, Button and Lee drove together from Brooklyn, leaving as usual at 4 a.m. White, who had enrolled in a master’s program in art history at the University of Massachusetts, drove from Amherst. Earlier, they had studied the transcript of Dennis’s last hearing, and were pleased with his performance. He’d been more talkative. “I thought it was a three-thousand-per-cent improvement,” Lee said.

Four days later, I sat down with Button and Lee, in a café in Manhattan, to hear about their visit. In the Auburn visiting room, they said, they had tried to keep the conversation focussed on strategies for Dennis’s hearing, but, as invariably happened, Dennis had other things he wanted to discuss. A friend had mailed him a pair of new work boots, but he wasn’t allowed to keep them, he said, because they were light brown with a black leather strip on top; prisoners weren’t allowed to have shoes of more than one color. Before the visit, Dennis had told Button on the phone, “Don’t forget the boots”—and Button had not forgotten to pick them up at the front desk on her way out of the prison. He had said that she could wear them or give them away; in the parking lot after leaving the prison, she had tried them on and found that they fit. But she decided, “I’m going to hold them until he gets out.”

Lee usually took charge at their visits, and this time she wanted to try a new strategy. Instead of talking about “if” he got parole, she insisted that they say “when.” Dennis was resistant. “The guys in here say ‘when,’ ‘when,’ ‘when,’ ” he said, “but I’m not going to do that, because, you know, the parole board could hit me however many times they want. You just don’t know.” Lee recalled, “I was, like, ‘Listen, Lloyd, I hear that. But we have to say “when.” I’m going to say “when,” and I need you to say “when,” because if you don’t imagine it, it’s not going to happen.’ ” Dennis played along. When the volunteers asked him what he wanted to do first after being released, he answered, “I want to go fishing.”

There was not a Parole Prep handout about the benefits of encouraging an incarcerated person to visualize his own freedom, but Lee thought that it might help Dennis work harder to prepare for the hearing. It would be easy for them to update his parole packet, but in the next five months, she said, “he has a lot of mental and emotional work to do.” They had assigned him the task of writing an apology letter—“That’s his homework,” Lee said—which they planned to include in his packet.

That spring, Lee was accepted into M.I.T.’s graduate program in urban planning. She quit her job in June and went to stay with her parents, outside Philadelphia. There, she worked on Dennis’s parole packet, reading and rereading his attempts at an apology letter. To her, they seemed slightly flat; she thought he still sounded like too much of a passive participant in his own crime. On July 8th, she borrowed her mother’s car and drove to Auburn. She recalled that, as soon as Dennis sat down in the visiting room, she said, “We have a lot to do today. I have to leave by one-thirty. So we have two hours, and we’re going to talk about the crime. It might be difficult, but that’s just what we’re going to do.”

In the past, when the volunteers had asked Dennis about his crime, he had told them that Patrolman Denton had approached him in a way that made him feel threatened. Sometimes he characterized his crime as an act of self-defense. At times, Lee thought that maybe even Dennis himself did not know why he had done it. His court file had been destroyed in a warehouse fire, and although the volunteers had read one or two news stories about the crime, they did not have a full understanding of what had occurred on July 24, 1971. If they had read his court file, they would have learned that witnesses had described a spontaneous, unprovoked attack.

In the visiting room at Auburn, Lee repeatedly grilled Dennis about that night, and made it clear that some of his answers were unsatisfactory. “You’re describing this as something that happened to you, and it’s not,” she said. “It’s something that you did.” She had heard him talk critically about the rapists he was imprisoned with, and she made it clear that she didn’t buy into the idea that someone who has committed rape is somehow a worse person than someone who has committed murder. “To a lot of people, what you have done is the worst thing that anyone could possibly do,” she said. Her words seemed to stun him; he said nothing and looked away.

The way Lee saw it, she was doing work that somebody else at the prison should have done decades earlier. “He should have been doing this work in therapy for his whole life with a social worker or psychologist or anyone, any qualified professional, which I am not—I’m definitely not,” she told me. “That would have made so much of a difference, because now the story that he tells himself has been cemented for all this time. And, for me, trying to push back on that now is really challenging.”

It seemed that the coping strategies Dennis had adopted were working against him. “The only way that he’s survived for this long—completely alone, completely isolated from his entire support network—is by totally closing off emotionally and relying on only himself,” Lee said. “He’s never been asked to do anything remotely emotional.” But, she said of the parole board, “what they’re asking for is something genuine and emotional.”

That night, Dennis called Button and told her about the visit. Button sent a text to Lee: “He called me and sounded really appreciative and said you helped him think in a new way. He also said, ‘You didn’t tell me you were sending in a pit bull.’ ”

By the late summer of 2019, Lee had moved to Cambridge to start classes at M.I.T., and White was about to begin his second year of graduate school in Amherst. Dennis appeared before the parole board for the thirteenth time on August 27th. Two days later, Button and her boyfriend rode their bikes to a restaurant in Crown Heights, and when they were locking them up she heard her cell phone vibrate inside her backpack. She pulled it out and read a message from Lee, who had just heard from Dennis: “He was denied.”

Button described that evening’s dinner as a “solemn meal.” A few days later, her boyfriend told her that she had been acting mean; she had been criticizing his every move, even his choice of light bulbs. “What’s going on with you?” he asked. “Nothing,” she said. “I just feel weird.” Then she started sobbing. She almost never cried, and she realized how much Dennis’s parole rejection, his second on the volunteers’ watch, had upset her. “The double denial is very demoralizing,” she said.

In October, she read the transcript of the parole interview. The lead commissioner was Marc Coppola, a former state senator who had once worked as a deputy sheriff in Buffalo. He’d started the interview by reading aloud a detailed description of the crime, and then asked Dennis, “Is there anything that you want to tell us about the offense and why you did this to the officer?”

Dennis said, “I was more or less out of control then from my drinking. I should have complied when the officers there approached me.” He went on, “When they started to ask me questions, I started to walk away from them, and . . . I guess that’s when I made my mistake. They put their hands on me and it led to an altercation.”

This response did not go over well. “The description in the record is very different than the description that you give, that they approached you,” Coppola said. According to the record in his parole file, Dennis had encountered only one officer, not two. “The record says there were other witnesses, that you came out unprovoked and stabbed him in the neck.” He continued, “Is it possible that you were intoxicated enough that you believe that’s how it happened, but maybe that’s not really how it happened?”

“Yes. I guess it’s possible, yes.”

Throughout the parole hearing, Coppola dominated the conversation, asking long-winded questions and speaking nearly three times as much as Dennis. He grilled Dennis repeatedly about the details of the crime; there was relatively little discussion about the forty-eight years that had followed, and just two questions about the plans Dennis had made for his release. The vote against his release was two to one. (Coppola declined to be interviewed.)

Button said of Dennis, “He said nothing new in that interview. Everything we practiced went out the window, because he is defensive and can’t really learn how to not be defensive, given his life story.” She continued, “I think people who do well in these interviews are guys who spend a lot of time in the law library in prison and have an inclination for speaking like their own lawyer. Some guys are good at being their own advocate and can tell when they need to reroute the conversation. But that’s a skill and not something everyone is good at. Definitely not Lloyd.”

Michelle Lewin told me, “I was so pissed. He had no way out with that board.” She started making calls and firing off e-mails, and soon found two attorneys, Ron Kuby and Rhiya Trivedi, to take on his case. They recently filed an appeal, arguing that the board had relied solely on the nature of his crime and not taken into account other factors. But appealing the board’s decision is a slow process, and Dennis’s next parole hearing, set for November of 2020, will likely take place before their efforts to appeal have concluded.

If that happens, Dennis will have to decide whether to take a chance with the parole board for the fourteenth time or wait for a judge to order an additional hearing. A judge does not have the authority to release him, so Dennis’s best hope would be to go before a board that was more likely to vote for his release. This past summer, five new commissioners—including a former Legal Aid attorney, a minister, and the former head of a prison watchdog group—joined the parole board. The Governor put forward a sixth candidate, who had once worked as a prison guard. On the day of the State Senate committee vote, Lewin and a few activists from RAPP camped out in the room and held up signs reading “Vote No!” The candidate was not confirmed.

Lee, White, and Button promised Dennis that they would continue to work with him. As fall approached, Button decided to take on another case with Parole Prep, too. She joined a team with two volunteers she did not know, and Lewin assigned them to work with a man at Otisville who has been incarcerated for thirty-six years. Button still sends letters to Dennis and speaks to him on the phone every week. In September, when she moved from one apartment in Bed-Stuy to another, she brought his new work boots with her, and now they are inside a suitcase in her closet. “I don’t know what to do with them,” she said. “We thought he was going to get out.” ♦