The Quality of Mercy

Gary Settle has helped dozens of federal prisoners get compassionate release. Will it ever be his turn to go home?

By Anna Altman

“The quality of mercy is not strained.
It droppeth as the gentle rain from heaven
Upon the place beneath. It is twice blessed:
It blesseth him that gives and him that takes.”

—William Shakespeare, The Merchant of Venice

It was February 2019, and Mary Price had rarely seen her office so busy. A wiry woman in her sixties with shoulder-length straight hair, Price is general counsel at FAMM, a nonprofit organization in Washington, D.C. FAMM is an acronym for Families Against Mandatory Minimums, and in addition to opposing severe sentencing, the group broadly advocates for the fair treatment of people in prisons across the United States. FAMM had recently sent out an edition of its newsletter, which supporters knew as the “FAMM Gram.” The response from readers began as a trickle, then became overwhelming, and for good reason: The newsletter outlined historic changes to the U.S. government’s compassionate release process.

Since the mid-1980s, federal prisoners have been able to seek compassionate release for what the law deems “extraordinary and compelling reasons”—including old age, terminal illness, and severe disability—by requesting that the Bureau of Prisons file a motion on their behalf in court. The BOP, however, rejects almost every request it receives. In January 2018, the Department of Justice reported that the BOP had approved less than 10 percent of the compassionate release applications it received over the previous four years, allowing just 306 people to go home. (Within the same time frame, 81 prisoners died waiting for the BOP to respond at all.) The DOJ’s Office of the Inspector General called the process “poorly managed,” with “inconsistent and ad hoc implementation [that] has likely resulted in potentially eligible inmates not being considered for release.”

For a long time, when the BOP denied a request, a prisoner had no recourse; the bureau’s decision was the final word. That changed in December 2018, following years of advocacy by FAMM and other groups, when Congress passed the First Step Act. Among other criminal-justice reforms, the law allowed a prisoner to file a motion for compassionate release directly with a federal judge if the BOP denied their request or didn’t respond to it within 30 days of receipt. FAMM was eager to share the news and connect eligible individuals with lawyers who could help them. Price knew the organization had to move quickly. “We were very concerned that people who were nearing the end of their lives or very sick would be going before judges without any help,” she said. “We couldn’t just leave these people on their own.”

FAMM’s newsletter was delivered to 40,000 incarcerated individuals via CorrLinks, the federal prison system’s email service. Price felt a thrill of anticipation—“a sense of stepping off into something that was unknown,” as she put it. She knew that sometimes a recipient would print a copy of the newsletter and pass it around the cellblock. Over days, then weeks, Price and her colleagues were inundated with hundreds of phone calls and emails from people seeking compassionate release or inquiring about the process for loved ones behind bars.

Amid the deluge, one inquiry stood out: It was written by a prisoner on behalf of someone else. The sender did not disclose his name. “I am writing this from the ‘Cancer’ floor of FMC Butner,” he wrote, referring to the Federal Medical Center in Butner, North Carolina. The five-story facility provides health care to some of America’s sickest male prisoners; it includes a psychiatric unit, a unit devoted to orthopedic surgery, and a cancer ward. “This is directed at the situation of another patient,” the sender wrote. “He is terminal and is unable to contact you directly.”

The sick man, R. Smith, had lung cancer. As Price later wrote in an article for the American Bar Association, he was in persistent pain and dependent on a feeding tube. With a prognosis of less than 12 months to live, and a sentence lasting much longer for distributing drugs, Smith applied to the BOP for compassionate release. But instead of going home, he was bound for FMC Butner’s hospice ward.

The anonymous person who contacted FAMM said that he had heard Smith crying to his family during a call on the ward pay phone. A longtime recipient of FAMM’s newsletter, the man knew that Smith might now have another way to seek compassionate release. With Smith’s permission, he was using Smith’s CorrLinks account. BOP policy forbade prisoners from using one another’s accounts, and the sender knew he risked punishment for doing so, which is why he left the message unsigned. He asked: Would FAMM consider helping Smith?

Smith’s case was exactly the kind Price had in mind when she drafted FAMM’s newsletter. FAMM connected Smith with an attorney, who began to prepare a legal motion. Meanwhile, according to Price, Smith got sicker. One of his lungs collapsed, and the man communicating with FAMM from inside Butner reported that Smith had been moved to an outside hospital better equipped to treat him. Smith’s lawyer couldn’t get updated information about his condition, but this wasn’t unusual: The BOP can be especially evasive about medical details near the end of a person’s life. “There’s no more cruel part of the BOP than this,” said a former federal defense attorney who spoke on condition of anonymity.

Smith’s lawyer filed an emergency motion in federal court for his release. The court then ordered the BOP to provide an account of Smith’s medical condition by that afternoon. The BOP didn’t meet the deadline, so the judge contacted Smith’s doctor directly. Upon learning how poorly Smith was doing, the judge ordered his release within ten days, as soon as appropriate transport could be arranged. No one could reach Smith in the hospital to deliver the news, so Price sent a message to the person at Butner working on his behalf. She hoped that he would find a way to tell Smith that he didn’t have to die behind bars.

Smith’s case was a turning point for FAMM’s work on compassionate release because it offered a blueprint for helping qualifying individuals. FAMM worked with the Washington Lawyers’ Committee for Civil Rights and Urban Affairs and the National Association of Criminal Defense Lawyers to expand the capacity of the Compassionate Release Clearinghouse, a newly created entity that recruited, trained, and supported lawyers representing sick or elderly prisoners requesting early release. In its first year, the Clearinghouse screened some 500 inquiries and placed more than 125 cases with lawyers.

Smith’s case also marked the start of a unique relationship. “Mr. Smith and his family are very lucky to have you in his corner,” Price wrote to the man who’d helped Smith. “We should all have friends like you.”

By then, Price knew the man’s name: Gary Settle. He was slow to tell her much about himself, but he continued to send CorrLinks messages to FAMM as he recruited more people at Butner for the Clearinghouse. In emails he sometimes used the moniker “P/H,” for “patient/helper,” in part to protect himself from BOP censure, and in part because he didn’t want to draw attention to himself. He felt that his personal story—including why he was serving 177 years in prison, along with his own cancer diagnosis—was beside the point.

Gary Settle as a child

Settle was born in 1966 in Hawthorne, California, a small city adjacent to South Central Los Angeles. His childhood had what he considered “storybook” elements: loving parents, a brother to horse around with, Little League games, family camping trips. In the summer his mother, Kay, took time off her waitressing job to drive the boys to the beach. Settle was bright—“so smart I could smack him,” Kay said. At age ten, he asked his mom for copies of Shakespeare’s plays, then named his cat Ophelia. “We weren’t rich in money, but we were happy, we had friends, there were always people over,” Settle wrote in a document he calls his “life story,” which he shared with me.

In time, Settle developed a rebellious streak. If Kay told him to stay within a few blocks of the house on his skateboard, he’d ride to busy areas downtown instead. When Settle was 13, his parents bought a farm in Ohio; his father thought the fresh air and country life would be good for the family. “We all had to learn on the fly all the farming tasks—feeding the cows, milking them and shoveling the other substances they produced by the wheelbarrow load,” Settle wrote. “If Green Acres hadn’t already been made, we would have had a great pilot.” It was a major transition for Settle: the unrelenting responsibility of farm work, the unfamiliarity of the local culture. His puka-shell necklace and faded Levi’s didn’t vibe with the rural Ohio style of bib overalls and John Deere hats.

Even so, he quickly made friends. He got into the habit of enlisting his buddies to help with household tasks. “Once, I told him he couldn’t go to a baseball game because he had to help with the chores,” Kay recalled, “and all of a sudden the whole team was weeding.” The town closest to his family’s farm had a single traffic light, two police officers, a barber shop, and “at least ten bars,” according to Settle. There was little to do, so he and his friends drank. Settle recalled being a happy drunk, outgoing and enthusiastic; he boasted that his charm was infectious.

Settle also liked to showboat—driving recklessly, hood surfing, doing motorcycle stunts. “I was not breaking any laws other than traffic ones,” he wrote. “Those I was shattering.” In fact, a juvenile court found him guilty of an offense when he was 17; the case records are sealed, but Settle said that the conviction stemmed from a fistfight he had with a man in his twenties. Looking back, he wondered whether spending his teenage years in a small town with few opportunities contributed to the course his life took.

In 1985, Settle got his high school sweetheart pregnant, and soon they married. At age 20, Settle had expenses and responsibilities, and he grew restless. When he heard about a gig with a construction company in Florida, he decided to move there with $400, two buddies, and no plan—he left his family behind for the time being. He and his friends arrived in time for spring break and blew all their money at Daytona. When Settle got a job, he had to sleep on a picnic table behind a church for a week, until he got his first paycheck.

Despite an inauspicious beginning in his new home, Settle worked hard, and he advanced from laborer to finisher and then to foreman. The construction company had contracts all over the Southeast, so Settle traveled, staying in motels. When the workday was over, he and his crew headed to strip clubs or hung out in bars.

Settle found a house big enough for his family; his wife gave birth to their son, Nathan, back in Ohio, then moved down to join him. In time Settle’s parents decided to relocate to Florida, too. Settle started his own construction company in Orange City, just north of Orlando. But for all that was changing, Settle still liked to spend his free time drinking with friends.

One day, after a few beers, he went to the drive-through window at a bank to deposit a check. He recognized the teller—she was a woman he knew from the local bar scene. “What do you want?” she asked with a smile. He replied, as a joke, “Give me all your money.” The woman bent out of sight and then reappeared holding a plastic container full of neatly stacked bills. “You mean this?” she asked, laughing.

A few weeks later, Settle ran into the woman at a bar, and she brought up their exchange at the bank, saying there had been $35,000 in the box. After their conversation, Settle couldn’t get the number out of his head. All that money, and so close he could have grabbed it.

At 27 years old, Settle was facing life in prison. It was all so uncanny—sitting there in a suit, knowing he would never be free again—that he almost felt compelled to laugh.

In October 1991, the Daytona Beach News-Journal reported that a tall white man with long brown hair and a mustache had walked into a bank during a Tuesday morning rainstorm. He was wearing the waistband of a woman’s stocking over his face and carrying a white bag. He vaulted the counter and pulled out a semiautomatic handgun, then took a stack of cash before fleeing on foot into a wooded area. Heavy rainfall prevented the sheriff’s helicopter from tracking him, and the dogs and deputies chasing him lost his trail.

It wasn’t Settle’s first robbery; he’d begun holding up banks and stealing cash the year prior. Most of the time, he didn’t run away—he stole a car from a bank clerk or customer. One time he approached a car with an elderly woman sitting behind the wheel. According to Settle, when she informed him that she needed her walker if she was going to get out, he pulled it from the trunk, got her to her feet, and then sped away. He could hear sirens in the distance.

By April 1992, the FBI was pursuing what it described to the West Volusia Sun-News as a “serial bank robber on the loose.” They believed that he was responsible for as many as seven bank robberies and one attempted robbery over an 18-month period. The criminal, the FBI said, was “armed, dangerous, and ready to strike again.”

That account didn’t square with how Settle saw himself. “It is embarrassing to admit this, and shameful to acknowledge,” he wrote later, “but in a way, I thought of the whole thing as a sort of prank or practical joke, with a big cash payoff.” According to Settle, he didn’t encounter any law enforcement, and he had no problem persuading tellers to cooperate. He was never in a bank for more than a minute or two, and he never hurt anyone physically. He saw his plunder as “free and easy money.” (A woman present during one of the robberies would later testify that her encounter with Settle scared her so much that she quit her job, and that she would “never be able to work again or be able to be alone again in the future.”)

Settle had accomplices—sometimes he had one drive a getaway car—and in September 1992, two of them decided to rob a bank on their own. They were caught before they succeeded, and during their interrogation they fingered Settle as the mastermind of the operation. Shortly after, Settle, who was on a trip to Boston at the time, was arrested for running a stop sign and driving under the influence. When police in Massachusetts ran his name through their databases, they—and Settle—learned that he was wanted in Florida on federal bank robbery charges.

Settle was indicted on March 18, 1993, on nine counts of bank robbery, one count of attempted bank robbery, one count of conspiracy, and ten counts of carrying a firearm while committing a violent crime. The government alleged that, in total, Settle had stolen around $190,000. “If I would have done something worthwhile with the money, I don’t think I would feel any better about things, but I might not feel so foolish,” he wrote. “The only people who really benefitted from the robberies would be various bartenders, waitresses, and strippers.” By the time he was indicted, Settle had separated from his wife. He later described himself as being at his “reckless, selfish worst.”

Settle pleaded not guilty, and he later claimed that he rejected a plea bargain that would have come with a relatively scant 12-year sentence had he testified against his accomplices. (The prosecutor denied making such an offer.) During pretrial detention, Settle twice attempted to escape from county jail. When his case finally went to trial in Orlando, he did what he could to appear serious, wearing a suit and taking notes. On May 11, 1993, the jury found him guilty of almost all the charges against him.

With his conviction on the books, Settle was subject to the Sentencing Reform Act of 1984, a result of congressional hand-wringing about rising crime rates that was later called “the most dramatic change in sentencing law and practice in our nation’s history” by the United States Sentencing Commission. The act sought to address what elected officials considered “undue leniency” in the criminal-justice system, as well as inconsistencies in sentencing around the country. Among other things, it abolished federal parole and created a system of mandatory penalties for certain crimes, giving judges less discretion over sentencing.

By the time Settle was tried, the mandatory minimum for a violent offense committed with a firearm was five years. If a person previously convicted of such a crime carried a gun during a second violent offense, the mandatory minimum was 20 years. How, though, should a court sentence someone found guilty of armed robbery for the first time, but on multiple counts in a single legal proceeding? As it happened, that exact question had been addressed just prior to Settle’s trial, in the 1993 Supreme Court case Deal v. United States. In a 6–3 decision, the court ruled that the harsher mandatory minimum should apply even in a single indictment.

When Settle was sentenced on August 30, 1993, the case law was so new that Judge Patricia Fawsett had to review it over a lunch recess. When she retook the bench, Fawsett sentenced Settle to a mandatory 2,127 months in prison, or just over 177 years: 12 for the robbery and conspiracy charges, and 165 for carrying a gun into a bank nine separate times. She ordered that he serve them consecutively.

Fawsett wasn’t inclined to be lenient, telling the defense that Settle showed “utter disregard for the law,” “a complete lack of remorse,” and “lack of concern for the terror he caused.” Still, she seemed troubled by the length of the sentence. “I do not think this is an appropriate result,” she said, “but I feel bound by the law as I understand and explained to you.”

Settle felt that Fawsett approached his sentence as if it were just a problem to solve; she even asked the attorneys present to check her math. At 27 years old, Settle was facing life in prison. It was all so uncanny—sitting there in a suit, knowing he would never be free again—that he almost felt compelled to laugh.

Adeel Bashir, a federal public defender currently working in the Middle District of Florida, where Settle was tried, told me that he has “only ever seen one other person get 2,000-plus months.” It’s the kind of sentence that would make a criminal-justice professional wonder whether the defendant had killed a child or was a serial pedophile. “To date, people ask me if Gary’s sentence is a typo,” Bashir said.

When Settle was transferred to a new facility, he almost always ran into someone he knew. Butner was no different, except that many of the people he recognized were dying.

Early during his time behind bars, at a prison in Atlanta, Settle tried to escape along with two other men—one of whom was the actor Woody Harrelson’s father—by scaling a wall using a makeshift rope. They surrendered when a guard fired a warning shot from a tower.

Settle spent the next two decades on a tour of federal prisons. He was housed for a few years at the infamous supermax facility in Florence, Colorado, where prisoners are kept in solitary confinement for more than 20 hours a day. That’s where Settle was when his father died in 1996. He had already used the one 15-minute phone call he was allowed that month when he heard the news, so he had to wait until the following month to call his mom to grieve with her.

By 2016, he had landed at U.S. Penitentiary Beaumont, which sits in the southeastern corner of Texas, half an hour from the Louisiana border, in a place known as the Golden Triangle because of its rich oil reserves. It’s also sometimes called Texas’s cancer belt because of its high cancer mortality rate. At Beaumont, routine bloodwork showed that Settle had an elevated level of prostate-specific antigen, or PSA, which is often used as the first indication of a prostate cancer diagnosis. According to Settle, he was not informed right away. “It takes a while in those places for the mill to grind,” he said.

At his next stop, USP Hazelton in West Virginia, Settle “started to feel weird.” He had been diagnosed with Graves’ disease, a thyroid disorder, and needed a double knee replacement. In 2018, doctors told him that his PSA was 50.5 nanograms per milliliter. Many physicians consider 4 ng/mL to be the point at which they recommend further testing to screen for cancer. Settle’s level, in other words, was astronomical.

He had a biopsy, which showed a very high likelihood of cancer. When doctors proposed removing his prostate, Settle declined; the surgery can have unpleasant side effects, including incontinence and erectile dysfunction. He asked for hormone therapy instead, and requested a transfer to a medical facility. After an extended back and forth, which Settle described as “a lot of gnashing of teeth and wailing of banshees,” the BOP sent him to FMC Butner for treatment.

After nearly three decades in federal prison, whenever Settle was transferred to a new facility, he almost always ran into someone he knew. Butner was no different, except that many of the people he recognized were dying. “I was shocked at the appearance and bearing of the prisoners I have known and the ones I did not,” he later wrote. “I was around people who looked like concentration camp inmates.”

Butner is one of seven federal facilities that serve very sick prisoners, some of whom wind up there because they didn’t get the treatment they needed to stave off serious illness. The law guarantees prisoners a constitutional right to health care—a right, ironically, afforded to no other group in the country—but in reality health care resources are limited behind bars, and potentially life-saving procedures are not always granted, even when they’re clinically indicated. A former federal public defender who spoke anonymously said that, in reviewing clients’ medical records, it’s not unusual to find someone who was told years prior by a prison doctor that they needed an immediate kidney transplant but never got one, or who had a heart condition requiring a visit to a specialist that the BOP never facilitated.

“Because most correctional health services are designed to cut costs and reduce perceived litigation risks, transparency and quality of care are not top priorities,” Homer Venters, a former chief medical officer for New York City’s jails, writes in his book Life and Death in Rikers Island. Prejudice also erodes standards of care. According to a DOJ report, “The belief that those convicted of serious crimes have somehow earned their suffering, as if the pain of illness and old age in prison were a part of the inmate’s just deserts … [is] widespread and intense among some custody personnel and … prevalent also among health care providers.”

Holding the prison system accountable for this bias is difficult. In a landmark 1976 case, the Supreme Court ruled that substandard medical care in prisons violates the Eighth Amendment’s prohibition against cruel and unusual punishment only if it rises to the level of “deliberate indifference” and not just “mere negligence.” The difference between these two concepts is the subject of an ongoing debate that prisoners have little power to influence. (In a statement, the BOP said, “We make every effort to ensure the physical, medical, and mental safety of inmates confined to our facilities through a controlled environment that is secure, humane, and in line with community standards of care.”)

At Butner, Settle learned that there was a saying for someone whose health showed a marked or rapid decline: He’s falling down. Paradoxically, this meant going up—to the fifth floor, where the hospice ward is located. A BOP PowerPoint presentation about Butner describes the hospice cells as private, with small nods at comfort such as flower-patterned quilts, pillows that match the blue cinder block walls, or a cushioned chair next to a bed. When Settle arrived, Butner held a monthly memorial service for the recently deceased. He said that a single service often honored as many as 30 people.

After beginning hormone therapy and radiation, Settle was able to maintain his strength and physical independence, so he considered himself lucky. In turn, he did what he could to help others. He noticed that one cancer patient, wheelchair-bound and too weak to push himself, would lock his chair to that of his cellmate, who would shuffle his feet to get them both around the halls. Settle offered to wheel them to meals and chemotherapy appointments, and gave the same assistance to others who couldn’t walk. “You’re not even really supposed to do that,” said Richard Hodge, who was incarcerated at Butner at the time. “Gary could have been wrote up for breaking the rules.”

Settle also assisted with hygiene, changing diapers on grown men. “I’m just putting myself in their perspective,” he said. “It’s got to be very humbling.” Settle reflected that he hadn’t cared for his son much when he was a baby; perhaps this was a way of atoning for that. (Settle was long divorced and hadn’t been in direct contact with his son in many years.)

When he read the FAMM newsletter about the Compassionate Release Clearinghouse, Settle saw another way he could help people. What was more important, he reasoned, than someone living out their last days in freedom, ideally surrounded by their loved ones? He made R. Smith his first project.

Compassionate release is grounded in the idea that changes to a person’s health may weaken the justification for their incarceration. What reason is there for imprisoning someone with Alzheimer’s when he no longer understands that he is being punished? When someone with late-stage liver disease can’t get out of bed and is no longer a threat to society? When “rehabilitation” is no longer feasible because a person has advanced cancer? “We’re not doing any social good, if we were in the first place, in keeping them locked up,” Price said. “And we can do a great deal of good in terms of helping people repair relationships and comfort each other and say goodbye.”

There is also a financial calculus that works in the BOP’s favor, one noted prominently in a 2013 DOJ report on compassionate release: It’s almost always cheaper to release sick people than to keep them locked up until they die. One study found that the annual cost of caring for just 21 seriously ill prisoners in California was almost $2 million per person, while the median per capita cost of nursing home care in the state was $73,000 per year.

After a judge allowed Smith to go home, Settle noticed a shift at Butner. He later wrote an email to FAMM, trying to put into words what he was witnessing. “In this place of death and dying, among incarcerated men who are holding on to life with nothing but more cells, more keys, more misery in their future, your efforts are having real, tangible results. Your efforts are giving hope,” he wrote. “You are giving life back to people, and you are giving them the most precious gift of all, time. Time to heal old wounds, to take a last breath of freedom and to leave this world with peace and dignity.”

FAMM worked closely with Settle through the summer and fall of 2019 to help people at Butner. “We didn’t appoint him,” Price said. “He appointed himself.” Settle made copies of FAMM’s newsletter and distributed them to his neighbors. He kept an eye out for people whose health was worsening and approached those he thought might qualify for compassionate release. He told them what he knew about the First Step Act, which he had studied, and about the Compassionate Release Clearinghouse. He spent six to eight hours a day requesting medical records, addressing envelopes, and updating his contacts on the outside about various cases. Settle read medical records, cross-referencing terms with a diagnostic manual and a medical encyclopedia he’d ordered, so he could send the most pertinent information about sick prisoners to their lawyers. Before long his cell was covered with piles of paper.

Settle also relayed information from incarcerated individuals to their family members. He helped people who were too sick to make it to a computer, those who had been transferred off-site for care, and others who had never learned to read or write. Sometimes he wrote compassionate release requests himself, parroting the language he had seen in other applications. The ones that went to the BOP were all but certain to be rejected or ignored, but that was part of the process: For a prisoner to file a motion directly with a judge, they first had to “exhaust administrative remedies,” in legal parlance.  

Word got around Butner about what Settle was doing. He would leave his cell after a nap to find four or five guys gathered outside, some of them in wheelchairs with paperwork in their laps. He was willing to assist just about anyone—he said he only refused people convicted of sex crimes. “Gary is able to form relationships with all kinds of people,” said Juliana Andonian, an attorney who used to work at FAMM. “He didn’t want to make himself the center of the story. That was really notable, the lack of ego.”

It isn’t uncommon for people in prison to help one another with legal matters. Jailhouse lawyers—some with legal training, some without—review statutes in a prison’s law library, file paperwork, and perform other tasks for fellow prisoners, often for a fee or some other form of compensation. “Someone less sincere could make a lot of money or do a lot of harm,” Andonian said. Settle refused payment, even to cover the cost of emails he sent and phone calls he made. The mother of a man Settle helped go home remembered sending him a thank-you note. “That’s about all he let me send him,” she said.

One day a thought dawned on Price. “He is doing this job that the Bureau of Prisons should be doing,” she said. “They should be moving heaven and earth to be sure that people are connected to family and loved ones when they’re near the end of their lives.”

Among the people Settle helped was a man in his thirties named Victor Webster, who was originally from Montana. Webster was in treatment for Ewing’s sarcoma, a rare cancer that occurs in or around the bones. He’d had the whole left side of his rib cage removed, followed by extensive chemo, but then a tumor developed on his chest plate. “His mental state was poor,” Settle said. “He assumed he was going to die in prison.” When Webster didn’t want to continue treatment, Settle pushed him in a wheelchair to his chemo appointments. He also got to work helping Webster obtain compassionate release.

Settle sent increasingly urgent emails to FAMM on Webster’s behalf, asking the group to move quickly. He visited Webster several times a day, until finally he was able to deliver the news that a judge had granted him immediate release. “I wish I had the ability to describe how the natural stoic look on his face collapsed or the strength of the hug I received from a guy I had been helping dress and stand up for weeks,” Settle said.

Webster went home in early July 2019. According to Settle, before he left he gave Settle a chain necklace with a cross, which he’d worn every day he was at Butner. Soon after he got home, Webster spoke with Settle and said he’d spent a wonderful Fourth of July with his family, including his nieces and nephews. They bought fireworks and set them off for him. Webster died that September. “It was sad it was just so short,” his mother, Debra Claassen, said of her son’s time at home.

The names and stories piled up. Von Skyler Cox, who had stage IV lung cancer and a prognosis of less than ten months, wrote to FAMM on behalf of “myself and my family and the ‘Patient/Helper’ ” after he was granted compassionate release in August 2019. “Your efforts have reminded me and many others that there are Great People in the world who have not forgotten us,” Cox wrote. Andonian printed out the email and put it on the office fridge. 

Settle noticed certain patterns—for instance, that a lot of the men granted release had been charged with crimes in blue states, where judges were perhaps more inclined toward compassion or less concerned about the political ramifications of releasing people from prison. (Recent research indicates that federal judges appointed by Democratic presidents are more likely to grant compassionate release than those put on the bench by Republicans.) According to Settle, some of the men who went home had been convicted of violent offenses, but he ruefully noted that they often had shorter sentences than he did.

He became swept up in the momentum. “Once I got going with it, I had to do it,” Settle said. “What type of person would I be if I did not assist people and their families at this most crucial time when I could?” He went on: “There is nothing I can do about the past, but I get to decide how I live the rest of my life.”

“Simply put, we are grateful for Gary, and awed by the care and compassion he shows for those in distress,” the FAMM letter said. “We have learned from him how to do our jobs better.”

In August 2019, about five months after they began corresponding, Price decided to meet Settle in person. “I want to make sure that he is safe doing this,” Andonian recalled Price telling her. According to Settle, the Butner staff were increasingly aware of his efforts to help people secure compassionate release, and their reactions were mixed. He had never gotten in trouble for using other people’s CorrLinks accounts, but some corrections officers told him he was “making them look bad.” He found that Butner employees with medical backgrounds tended to be more receptive, even expediting his requests for medical records and quietly referring patients to him. Still, to Settle they seemed jaded, like “how you would be if you worked in a dog pound and you get to see sick animals that they put down.”

Price’s job doesn’t put her into a lot of direct, consistent contact with people in prison. Rather, her role is usually to assess a person’s needs and connect them with resources. On her way to North Carolina, Price’s overriding feeling was curiosity—who was this person who had committed himself to advocating on behalf of others? She and Settle spent an afternoon together in Butner’s visiting room. As the hours wore on, Price asked Settle if he wanted anything from the vending machine; steadfast in his policy of not accepting any gifts, he politely refused. Water was free, “so we drank a lot of water,” Price said.

After the visit, Settle gradually began corresponding with Price as a friend. She told him about what she was growing in her garden and described a recent whale-watching vacation. He talked about his mother, Kay, whom he worried about all the time, and what he was reading. Price sent him books she thought he might like, including a trilogy by Ivan Doig and two books of poetry; one, by Ada Limón, Settle saved until Christmas to read as a treat. When Price was sick, Settle asked his mother to send her flowers.

That December, Andonian, Price, and another FAMM employee, Debi Campbell, asked Settle if they could write a letter to Kay. “I knew him well enough to know his mom was his treasure,” Andonian said. The FAMM team wanted to tell Kay how much Settle had come to mean to them. Settle consented.

“Gary, who calls himself the ‘patient/helper,’ impressed us immediately,” the letter to Kay read. “He follows up conscientiously on each and every person he works with. Beyond winning or losing, he cares about their spirits.” The FAMM staff said that, by their count, Settle had helped 19 people obtain release, allowing them to spend their last days with their families. “Simply put, we are grateful for Gary, and awed by the care and compassion he shows for those in distress,” the letter continued. “We have learned from him how to do our jobs better.”

Soon Settle’s assistance would become more urgent than ever.

Overcrowding, unsanitary facilities, poor medical care—those were just some of the reasons COVID was able to tear through U.S. prisons at astonishing speed. Within weeks of the virus being declared a national emergency, rates of infection in prisons far outpaced those in the population at large. By the end of April 2020, eight of the country’s ten largest COVID outbreaks were in prisons or jails. Still, the BOP was slow to implement masking, social-distancing, and testing policies. Some incarcerated individuals were scared to report symptoms because it meant being sent to solitary confinement.

Butner was hit particularly hard. With its medically vulnerable population, including many cancer patients, the facility was practically a showcase for the comorbidities that can make people who contract COVID especially susceptible to severe illness or death. By late July 2020, a remote inspection by the DOJ’s Office of the Inspector General found that 1,020 people imprisoned at Butner had COVID, and that 25 of them, along with at least one staff member, had died. Later, in the fall 2021, the ACLU would report that Butner had more than twice the number of COVID fatalities as any other federal prison. (The ACLU and Washington Lawyers’ Committee for Civil Rights and Urban Affairs filed a lawsuit against the BOP over its handling of COVID at Butner, but a judge dismissed the case over procedural questions.)

The BOP has policies about notifying family members if a prisoner becomes seriously ill, but these are not always strictly followed. At the height of the pandemic, loved ones often struggled to obtain updated information. One former federal defender who spoke on condition of anonymity described receiving calls from people who were desperate to know about their loved ones. I haven’t heard from my son in a month, they said; or I don’t know if my brother is in a hospital unconscious or just in quarantine. “It created so much panic for family members,” the former federal defender told me.

The Coronavirus Aid, Relief, and Economic Security Act, passed in March 2020, expanded the BOP’s authority to place prisoners in home confinement for a portion of their sentence. Prisoners don’t have to apply for this sort of transfer, so Attorney General William Barr directed the BOP to identify “suitable candidates”—those with COVID comorbidities, convictions for nonviolent crimes, and low risk of recidivism. According to data from the Marshall Project, the BOP placed nearly 5 percent of its incarcerated population in home confinement by October 2020. But at Butner, among other places, the bureau dragged its feet. The DOJ would later estimate that although 1,070 people at Butner may have been eligible for home confinement as early as April 2020, the BOP had released only 68 by July.

Meanwhile, according to the Marshall Project, the BOP didn’t budge from its usual stance on compassionate release, approving less than 1 percent of the more than 31,000 requests it received in the first year of the pandemic. A 2022 NPR analysis later found that at least one in four federal prisoners who died of COVID had sought compassionate release. (In a statement, the BOP said that it “carefully followed updates from the CDC, and guidance was provided to our facilities” about protective measures. With regard to compassionate release, the bureau gave a brief summary of the request process and noted that “the decision on whether to grant such a motion … lies with the sentencing court.”)

Hoping that it could help people get home before it was too late, FAMM ramped up the work of the Clearinghouse, recruiting an army of attorneys and paralegals to get release requests before the courts. It decided to support appeals from prisoners with vulnerabilities to severe COVID infection, which under the unprecedented circumstances might legally qualify as “extraordinary and compelling reasons” for early release. Prior to the pandemic, the Clearinghouse had screened about 500 requests for assistance and helped some 60 people go home. From the start of the pandemic to the end of 2021, nearly 5,500 requests came in. People wrote about having asthma, compromised immune systems, cancer. They were terrified of contracting COVID and dying. From the flood of communication, Clearinghouse attorneys were able to file 1,069 motions for compassionate release in the first year of COVID, 205 of which were granted.

At Butner, Settle threw himself into helping people, including Richard Hodge, who was serving 98 months for conspiracy to distribute drugs. Hodge had received two organ transplants before he arrived at Butner, and when he contracted COVID, the virus hit him hard. As his body struggled to clear the infection, he could barely stand up to use the bathroom. He didn’t eat for ten days, and he lost about 30 pounds. He later claimed that, despite having a compromised immune system, he was given “no treatment whatsoever.” Hodge said that the Butner staff was indifferent, at most checking his temperature and blood pressure. “You either survive or you don’t, that was their mentality,” he told me. (In a statement, the BOP said, “We do not comment on anecdotal allegations or, for privacy and security reasons, discuss the conditions of confinement for any inmate or group of inmates.”)

Settle implored Hodge to seek compassionate release, lest there be a worse outcome if he got COVID a second time. “He kept after me,” Hodge said. “I didn’t think I had anything coming, but Gary kept insisting.” Settle helped Hodge file his compassionate release application with the BOP to exhaust his administrative remedies and connected him with FAMM and an attorney. “Gary had all the information,” Hodge said.

In March 2021, a judge granted Hodge’s request; he was a free man. He went home to Laurel County, Kentucky, where he could receive specialized care at a transplant clinic and spend time with his kids and grandkids. “It was all because of you my friend,” Hodge later wrote to Settle in an email. “I owe you so much, and I wish there was some way I could bring you out of there bub.”

“I have a very small family, but I dream of an opportunity to be part of their lives,” Settle wrote. “I am humbly asking that you please consider giving me that opportunity and you have my word, you will never have cause to regret it.”

In July 2020, Andonian encouraged Settle to seek compassionate release. Thanks to hormone therapy, Settle’s prostate cancer was in remission, but he had other medical conditions that could increase his risk of severe COVID. Initially, Settle was not in favor. “I felt I did not qualify,” he said. “I thought that the finite amount of resources FAMM had at their disposal would be better used to assist some of the very sick prisoners I knew.” Andonian urged him to reconsider. She told him how deserving he was.

After they spoke, Settle went back to his cell and broke down in tears. “I’m not sure if my familiarity with the process made it more powerful,” he said, “but it was an overwhelming sense of gratitude, happiness, and other emotions.”

With Andonian’s help, two attorneys filed a motion on Settle’s behalf on January 27, 2021. It highlighted the threat COVID posed to him, his work helping people seek compassionate release, and his unusually onerous sentence. The First Step Act, which had made compassionate release more accessible, also gave judges expanded discretion to reduce sentences, especially mandatory minimums. “During his almost three decades of incarceration, Mr. Settle has grown from a reckless young man into a thoughtful middle-aged man known for the meaningful relationships he builds with others,” the motion read. “Mr. Settle’s extraordinary acts of service while in prison demonstrate his sincere rehabilitation and underscore that the period of incarceration imposed by the Court has served its intended purpose and should be amended to time served.”

The motion contained letters from people Settle had helped and from Victor Webster’s mother. They praised Settle for being “above prison politics” and for helping people exercise their rights. “In a place full of hate this guy oozed with love,” one stated. “[I] would love to see him in regular clothes, see how fast or how slow he drives.” A cancer survivor reflected on Settle’s compassion: “When I was mentally down Mr. Settle would come into my cell and sit for hours at a time listening to me.” Webster’s mother said she would be “forever grateful” that Settle helped ensure that her son could die at home in Montana.

Settle also made a direct appeal to the judge reviewing his request. He wrote that while he couldn’t explain the decisions he made as a young man, he had tried to be a better person since. What weighed on him most was being away from his family, especially his mother. “My own medical situation over the last few years has exposed me to the fragile nature of life and the importance and lasting value of family connections,” he wrote. He hoped to reconnect with his son, meet his grandchildren, and care for his mother as she aged. “I have a very small family, but I dream of an opportunity to be part of their lives,” he wrote. “I am humbly asking that you please consider giving me that opportunity and you have my word, you will never have cause to regret it.”

On March 5, 2021, Judge Carlos Mendoza of the Middle District of Florida denied Settle’s motion. He ruled that Settle’s health issues didn’t meet the criteria for compassionate release—he wasn’t terminal, and he could care for himself. “Covid-19 alone is not an extraordinary and compelling reason to grant release,” Mendoza said. In his view, reducing Settle’s sentence would minimize the seriousness of his offense, and “protecting the public remains a paramount consideration.” In other words, Mendoza considered Settle to be a threat to society.

The ruling was a gut punch to Settle and his supporters. “I was disappointed—I still am—by the shortsightedness of the judicial inquiry,” Andonian later said.

Eleven days after Settle’s request was denied, his physician contacted him with more bad news: The cancer was back. Mendoza had ruled on outdated information.

Settle knew of people who were granted compassionate release but, because they had no family to help them, died in prison as free men.

I began communicating with Settle in July 2021. I had read Price’s American Bar Association article about the work FAMM was doing on compassionate release, which referred to Settle’s crucial role without mentioning him by name. I asked the FAMM staff if the anonymous helper was amenable to having his story told. Andonian said that he was.

Settle and I had just one exchange on CorrLinks and a single phone call before his communication privileges were taken away. According to an incident report he later shared with me, he was written up for speaking to a member of the media without following “special mail procedures”—he had not obtained the prison’s permission before speaking with a journalist. Settle said that he was also placed in solitary confinement for two weeks. He eventually had his privileges restored, and for the next few months he called me several times a week. In chunks of no more than 15 minutes, due to the prison’s time limit on outgoing calls, he told me about his life and the people he’d helped send home.

That November, Settle wrote to say that his cancer had spread. A PET scan showed that it was in his lymph nodes, making it stage IV. He was starting treatment: hormone therapy again, along with eight rounds of chemo and perhaps radiation. He wrote that he saw cancer “as a challenge, as a fight I will be in till it’s over.”

He reported, too, that a social worker had told him he met the criteria for compassionate release—a coded way, Settle knew from his work with FAMM, of saying that he had less than 18 months to live. There was no guarantee he would get out, but given his new prognosis, he could ask the courts to consider his case a second time. Doing that would mean breaking his mother’s heart in a new way: Settle had avoided telling Kay about his cancer diagnosis—she thought that he’d filed his first compassionate release motion because his Graves’ disease heightened his COVID risk. He lied because Kay was a cancer survivor and because his father had died of the disease. He didn’t want to cause his mother anguish. Now, though, he had to tell her: If he requested compassionate release, the BOP would contact Kay to vet her as a suitable end-of-life caregiver. (Settle knew of people who were granted compassionate release but, because they had no family to help them, died in prison as free men.)

Settle said that telling his mom about his cancer was “the hardest thing I have ever done.” Kay told me she didn’t “scrape, rant, or rave” when she heard the news. She just asked “what number” the cancer was. “We’re going to beat this,” she told her son. Settle wept.

Settle found himself comparing his own situation with those of the people he was helping. He observed what happened to his neighbors as their bodies broke down and to the compassionate release motions of people with advanced metastatic cancer. He saw people with long histories of incarceration and multiple convictions, including for violent offenses, be sent home.

There were signs that his case might go the same way. Prison wardens are apt to deny compassionate release requests, stymieing them before they can even get to the BOP’s Central Office for final review, but Butner’s warden agreed that Settle met the criteria and recommended him for release. The response came as a surprise; for Settle it also confirmed just how poor his prognosis was.

While Settle waited to hear from the BOP, his legal team prepared to take his request to court if it was denied. Juliann Welch and Adeel Bashir, federal defense attorneys in the Florida district where Settle was originally tried, agreed to helm the effort, while Price and others at FAMM would offer guidance and support. Settle referred to them as Team Gary. The existence of a support squad strategizing about his case astonished him. “Up until a few years ago, I was Team Gary,” he said.

The omicron variant was racing through Butner when the BOP’s Central Office overrode the warden and denied Settle’s request, noting that his release “would minimize the severity of his offense and pose a danger to the community.” Settle and his lawyers now had to prepare to once again go before Judge Mendoza, who was still on the bench with jurisdiction over the case. Given Mendoza’s previous ruling, Team Gary hoped to get the U.S. attorney assigned to the case to support Settle’s release. It would be harder, they reasoned, for Mendoza to say no to both the defense and the state.

Welch and Bashir sent a package of materials to the U.S. attorney’s office, including character references and notes from medical experts who had evaluated Settle’s health records. A doctor concluded that although Settle would recover from the side effects of cancer treatment, he would require increasing amounts of assistance and ultimately need around-the-clock care, “either in a palliative or hospice setting.” A nurse at Butner who had cared for Settle wrote that she thought there was essentially zero chance he would reoffend. Research supported her intuition: The DOJ found in 2013 that only 3.5 percent of people granted compassionate release reoffended, compared with 41 percent of all individuals discharged from federal prison.

Still, Welch and Bashir offered concessions—a period of home confinement, for example, or an ankle monitor—that they hoped would guard against the judge’s concerns that Settle might still be dangerous. “The hurdle we have to get over is convincing the court that he’s also deserving,” Welch said, “because all of this is very firmly discretionary.”

Settle waited to learn about his fate. As weeks and then months ticked by, our email exchanges and phone conversations became less focused, more desultory. I had fewer pointed questions for Settle to answer before the phone line cut off. He told me about what he was reading: The Economist, The Wall Street Journal, Neal Stephenson books. He bemoaned that his 82-year-old mother still insisted on climbing a ladder to clean her gutters. He told stories, including one about visiting his grandparents when he was a child. Settle recalled clambering up a cherry tree even though he’d been told it was too weak to hold him. When he fell, he was stunned more than hurt, but still he began to cry. His grandfather gruffly told him to get up, adding, “If you’re going to be stupid, you’re going to have to be tough.”

Settle told me he still tried to live by that way of thinking. “I brought this on myself,” he said, not for the first time, about his incarceration. There was no point in complaining. “Except about the sentence,” he added dryly. “I’ll complain about that.”

Sometimes Settle slipped into dark moods. He was serving a life sentence with a life-limiting illness, and he was surrounded by people in a similar position. It was a lot to bear. “Anxious and impatient could be my middle names,” he said.

He tried to stay busy, even while undergoing cancer treatment. He worked on compassionate release motions for his neighbors and spent time on his own case, hoping to help Team Gary. He sent Welch a copy of his medical records—even though she already had them—highlighting what he considered the most important parts. He kept track of side effects from his treatment, including mouth sores, debilitating fatigue, and a numb left leg, so that no one could claim he was tolerating it well. He counted how many pills he took: 39 on most days, 51 when he had chemo. He had never slept comfortably in prison, and the steroids he was now taking didn’t help. He made sure to exercise and drink plenty of water, but eating healthy could be challenging: According to Price, the prison gave Settle only one piece of fruit—a banana—per week, and the “salad” on offer was just lettuce.

Settle allowed himself to consider what life outside prison would be like. He wanted to speak to at-risk youth, to cook the food he liked to eat, to submerge himself in water for the first time in almost 30 years—“preferably swimming but I will settle for a good soak in a tub,” he said. Kay, too, fantasized about the contented time she might have with her son. She had a room ready for him in her home, and she looked forward to going to the beach and sitting on her patio together, enjoying the view. “It’s going to be a whole new world,” she said.

Settle also hoped that if he was released he might get better treatment, buy more time. Kay felt the same way—in our conversations, she kept mentioning the urgency of getting her son to a “good doctor.” Sometimes it felt as though Settle and his mother had allowed themselves to believe that the terminal diagnosis only applied within prison walls. I wondered, if Settle were released, how it would feel to face the knowledge that he would still die of a painful disease.

When Settle saw his oncologist, he peppered the doctor with questions: Why was he having pain in his back? Could it be an indication that the cancer had spread to his bones? Bone metastases were notoriously painful and hard to treat; developing them was one of his biggest fears. According to Settle, the oncologist told him, “You look too good to be that sick!”

Settle said that he didn’t keep in touch with many people when he was feeling low, but he spoke to me because it made him feel “muse-like.” He mentioned the author John Irving, who has said that he liked to start a new novel by writing the last line first. “With that idea in mind,” Gary wrote to me, “how does some variation of this ending sound: ‘And Gary walked out the prison door….’?”

After he heard the news, Settle called me and barked a mock headline for my story: “Not Terminal Enough!”

Early in the spring of 2022, the assistant U.S. attorney who had reviewed the materials sent by Welch and Bashir announced that she would not support Settle’s motion for compassionate release. She believed that, even in his diminished state, he posed too great a risk to society. A social worker who advocates for people to be released from prison due to serious illness told me that she often sees prosecutors take this approach: “They want them to be on death’s door.”

After he heard the news, Settle called me and barked a mock headline for my story: “Not Terminal Enough!”

Once again it felt as if a decision was being made based on out-of-date information. In April, a scan indicated that Settle’s cancer may have spread to his spinal column. His wrists had become so weak, likely from arthritis, that he was wearing splints that reached to his elbows. By May, he couldn’t hold a toothbrush and barely managed to secure the large buttons on his prison uniform. Due to weakness in one of his legs, likely caused by metastases pressing on his sciatic nerve, he was issued a walker. It went without saying that even if he wanted to rob a bank, he couldn’t easily enter one, much less hold a gun or get away quickly.

His deteriorating condition led to accidents: Settle burned his arm when he spilled hot liquid on it, and he had a couple of falls. He could no longer push his wheelchair-bound friends to meals. “This is a really hard time for him, a really hard transformation from being the person who gives and supports to being the person who has to be supported,” Price said after visiting Settle that spring.

There is no limit to the number of times a person can apply for compassionate release, but Settle’s attorneys believed that he probably had one more shot. For Team Gary, the question became whether to file the motion with Mendoza, despite the assistant U.S. attorney’s lack of support, or wait until Settle was even sicker. Settle was resolute: He wanted to file and be done with the uncertainty.

On May 27, 2022, he tested positive for COVID. The symptoms started with nausea and vomiting; eventually, he developed fever, chills, and trouble breathing. He was placed in isolation. He later told me that he survived for three days on cough drops and water.

Settle’s lawyers filed his motion for compassionate release on May 31, with a request that it be expedited because of his COVID infection. They laid out Settle’s “changed medical circumstances” and the Butner warden’s determination that Gary met the criteria for a reduced sentence, even though his superiors disagreed. They emphasized that with his “imminent, continued, and significant physical decline consequent to his incurable condition,” along with his utter lack of inclination to reoffend and his demonstrated remorse and rehabilitation, he didn’t pose a danger to the public. Releasing Gary “does not undermine respect for the law,” the motion read. In an interview, Welch put it more bluntly: “His case is what the government had in mind when they wrote the compassionate release statute.”

In response to the motion, Mendoza called an in-person hearing—an unusual move. Settle and his lawyers hoped that meant the judge was seriously considering granting his release. The hearing took place on a hot summer day in Orlando, and it lasted about 45 minutes. Mendoza asked questions about Settle’s health and disciplinary record, and he raised several concerns: Why had Settle never sent apology letters to the people he had terrorized during his robberies? Why had he waited so long to express remorse? Welch read a statement Settle had written, and Mendoza seemed receptive. “It appears as if he’s accepting responsibility for what he did,” the judge said. Welch then requested that, should Mendoza not yet deem Settle ready for release, he consider abeyance—hitting the pause button on the motion—so that when Settle’s condition worsened, as it inevitably would, the motion could be considered again.

Mendoza said that he needed time to think. “This is a very difficult decision I’m being asked to make,” he said before adjourning the hearing.

A month later, Mendoza scheduled another hearing, this one by telephone. Within moments of starting the call, he dashed Team Gary’s hopes. The judge told Bashir, who attended the hearing on Settle’s behalf, that he saw no examples of Settle’s rehabilitation and remained concerned about his disciplinary record. Moreover, Mendoza said he found Settle’s statement of remorse disingenuous, given that he’d waited until he was seeking release to express it, and had never directly asked his victims for forgiveness. For those reasons, Mendoza concluded, the motion for compassionate release was denied. He did not allow for comment before ending the hearing.

Afterward, Price at FAMM got a call from Settle. He hadn’t been able to reach Bashir and figured Price might know how Mendoza had ruled. Price had heard the news. “I was deeply saddened by the denial and outraged by the form it took,” she wrote to me in an email. When she saw that Settle was calling, she didn’t answer—she thought it was better that he speak to his attorneys. But when he called a second time, she answered.

“So what happened?” Settle asked. Price, who had begun to weep, didn’t know what to say, so she hesitated. “OK,” Settle said in response to her silence. “I know.”

Settle then called Kay to tell her that he wouldn’t be coming home. “I am not going to say any more, as we are both going to cry,” he told his mom, though in truth he was already crying. Then he hung up the phone.

“It’s a process I trust and believe in that failed me,” Settle said. “I’m so glad the law exists even if it doesn’t help me. It’s my bad luck.”

I first requested a visit with Settle in April 2022, when Butner was still operating under tight restrictions because of COVID. In late summer, as case numbers went down and social distancing eased, I filed another request. Despite persistent prodding, months went by without a response. Price wrote to the BOP, reiterating that Settle had a right to speak to the press. “Mr. Settle is dying. Delay may be a denial,” she noted. Finally, in December, I was informed that I could have a one-hour visit with Settle. I would not be allowed to bring recording equipment.

On a bright, unseasonably warm January morning, I arrived in North Carolina’s Research Triangle. The sky was a limpid blue as I made my way to Butner, along pine-forest-lined roads with entrances to the corporate facilities of Novo Nordisk and Merck. When I turned onto Federal Center for Correctional Research Road, I was trailing an ambulance. The complex was eerily quiet. No one was in the yard, and no guards were visible.

Passing through security, I noticed wood cutouts of motivational phrases—Respect, Correctional Excellence, Integrity, Courage—hanging on the white cinder block walls. A TV screen in one corner flashed the phrase “Kindness is giving hope to those who think they are all alone in the world.” I was escorted to the visiting area by an officer wearing a bulletproof vest. Gray chairs were tipped against tables and stacked against the wall. There was no one else there. I asked the officer if I could shake Settle’s hand or hug him when he arrived and was granted permission.

Settle rolled into the room in his wheelchair wearing Timberland-style work boots and a jumpsuit with his name and prisoner ID number on the left breast. He stood up to embrace me, then moved to a regular chair. We had spoken on the phone scores of times, totaling a dozen hours or more, and I felt like I knew him well. But being in someone’s presence always brings new knowledge of them. Settle’s eyes were a bright golden brown, and his silver hair had been cut the day before, making it bristly.

The officer left us alone for the hour, and I decided to treat our meeting not as an interview but as a chance to be together. We talked about how angry Settle was when he first got to prison (“I just wanted to punch someone—I had no patience for anything”) and about forgiveness, namely his difficulty granting it to himself. He showed me photographs of his grandchildren and teared up when he talked about his mom, as he often did. He reflected on Mendoza’s denial and on the fact that he had allowed himself to hope for a better outcome.

Since the visit we have remained in touch, and almost every time we speak, Settle talks about a new compassionate release case he’s working on or another Butner prisoner who finally made it home. He told me that his story is “fairly well known” around Butner, and that people give him “pitying looks.” His friends, both inside and out, are frustrated on his behalf. “It really saddens me to know that with all he’s done for other people, and his medical condition now, that he isn’t at home with his family,” Richard Hodge wrote in an email. For her part, Price said, “He deserves better.”

Settle described compassionate release as “a process I trust and believe in that failed me.” With his own path foreclosed, Settle will likely die in prison. His only chance for a different end to his story is clemency, about which he is understandably pessimistic: Clemency petitions move through the Department of Justice at a glacial pace—it can be years before an answer comes—and a vanishingly small number are approved. The Trump administration approved only about 2 percent of the clemency requests it received, and the Biden administration is on track for roughly the same number. Still, Settle has decided to submit a request, with the support of Price and others.

Lately, Settle has been wrestling with whether he should continue cancer treatment. He has outlived his 18-month prognosis, and while his pain is constant and his mobility compromised, a recent CT scan showed that his tumors have stopped growing. His PSA has doubled, however, and doctors have recommended further hormone therapy. He isn’t sure he should bother. “I haven’t come to a full decision yet on whether to fight,” he said.

Before our visit at Butner, Settle sent me an essay he wrote—the title, a nod to Viktor Frankl, was “A man’s search for a reason to live.” In it, Settle reflected on his road to Butner and the toll of his cancer treatment, writing that it had “devastated” him physically and spiritually. “Maybe the latter was because I could not rationalize why I was undergoing such debilitating treatment when the effects of it were intended to extend my ‘life,’ ” he surmised. “This is not to say that I felt like dying during that time, or now. But my thoughts were simply, why? What do I have to look forward to?”

In trying to answer this question, he found himself reflecting on the work he’d done with FAMM. By his count, he had helped 42 people secure compassionate release. He wrote that he was glad to be part of an effort that brought hope to people in a hopeless place, and was honored to have met Price, Andonian, and others. “With my life experience it is not surprising that I was unused to communicating and interacting with people of this caliber,” Settle wrote. “That many of them have become dear and true friends is even more than surprising, it is humbling.”

“If I hang around for a little while, who knows what impact I can have?” he concluded. “In testament to the love and respect I have for my friends and to honor their work is reason enough for anyone to continue to live, even in here.”

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