Heading out the door? Read this article on the new Outside+ app available now on iOS devices for members! Download the app.

Early on the morning of August 20, 2015, Kahlil Gonzalez boarded a bus at Franklin Correctional Facility, in northernmost New York State. The bus had tinted windows and signs that warned other drivers of the prisoners within. Handcuffed and chained to another inmate, Kahlil sat on one of the seats and gazed out the windows as the transport meandered south. Passing motorists stared back, straining to look at the men inside. Kahlil felt as if he were part of a “zoo exhibit, like some dangerous animal.”

He was on his way to a downstate facility that housed inmates for short-term stays: the newly convicted, transfers and, as in Kahlil’s case, those due to be released.

Kahlil was 35. He had been locked up for more than seven years, on burglary charges. He was anxious to be out, and the bus ride gave him plenty of time to think. Long-incubated plans swirled through his head. He thought about jobs and housing, and running.

He had run nearly 2,500 miles in prison. Before Franklin, Kahlil had been housed in Livingston Correctional Facility, in the western part of the state. A grassy rectangle with concrete ball courts in one corner and a .4-mile dirt path around the perimeter, Livingston’s yard resembled a medium-size city park. In fair weather it would fill with hundreds of prisoners.

The yard was surrounded by two 20-foot fences with spools of razor wire on top. Every few minutes, an armed guard in a pickup drove past on a gravel road; sometimes, he’d wave to Kahlil, running just inside the barrier. Beyond the road were cornfields and farm equipment and, far in the distance, thickly wooded hills that Kahlil dreamt of exploring. “You don’t have any idea what’s out there,” he says, “but you know it’s better than where you are.”

During the first years of his sentence, Kahlil had been involved with a prison gang. Later on, when he tried to put that kind of trouble behind him, running helped. “Running had a rehabilitative energy to it,” he says today. “It just makes you want to stay away from shit that could possibly take running from you.” In a letter to this magazine written during his last year in prison, Kahlil described how running took him to “some greater place” where he was “oblivious to the intimidating concertina-wire.”

The bus ride lasted nearly 18 hours. Kahlil arrived at the receiving facility around 10:45 p.m., then was woken at 6 a.m. and released around midday. His father, Omar, waited in the parking lot, crying. They hadn’t seen each other in five years. Kahlil was struck by how much his father had aged. “It was a wakeup call,” he says. “I had been gone a long time.”

During the two-hour drive to Westchester County, where he grew up, Kahlil thought about readjusting after so much time away. Excitedly, he told his father about trails he wanted to run and gear he wanted to buy, but running would be an adjustment, too. In prison, few people ran, and Kahlil had been impressive by default—the New York State penal system’s very own Forrest Gump. Now, he wondered how his flat prison-yard training would transfer to the Northeast’s rugged terrain—and how other runners would receive him. He had admired the trail-running community from afar, but was unsure whether its members would want anything to do with a newly released felon.

Kahlil found delight in the simplest things during that first car ride. He marveled at the plush cushions in his father’s SUV. He fiddled with the radio and opened his window. He played with Omar’s smartphone, amazed. And as he looked out at the other cars, he realized something odd: No one was staring. I’m just a regular person, he thought. I’m not shocking anymore.

Kahlil Gonzalez at home in New Rochelle, New York.
Kahlil at home in New Rochelle, New York.

Eight months later, when I visited him in April, Kahlil was tapering for a 50K in Bear Mountain, New York. That is, he was trying to taper, but doing a pretty poor job. Six days out from the race, he followed a 13-mile road run with a 15-mile bike ride and, later, a few quick sets of pushups.

Kahlil is five-five but not diminutive, with a fighter’s build. His close-cropped hair is flecked with silver, and his long, angular face often relaxes into an impish grin. He has a riffing sense of humor and abundant energy that, when not channeled into running, converts itself into nonstop chatter. “If I don’t exercise, people are like, ‘All right, somebody give him a Valium or something,’” he joked at one point. He tends to pinball off various topics—dog breeds, VO2 max, Kilian Jornet, the gentrification of Brooklyn—before returning, with unexpected precision, to whatever he had been talking about moments before.

Kahlil works in Brooklyn, as a case manager for a personal-injury law firm. He lives just north of the city, in New Rochelle, a medium-size town of quiet neighborhoods around a denser urban core. One afternoon, we sat in the room he rents. An expensive road bike, a gift from his mother, occupied one corner, next to a bookshelf that held, among other titles, The Competitive Runner’s Handbook, Your Magic Power to Be Rich! and Nietzsche’s Human, All Too Human.

A consummate New Yorker, Kahlil Gonzalez has a tattoo of the pre-9/11 World Trade Center on his calf.
A consummate New Yorker, Kahlil has a tattoo of the pre-9/11 World Trade Center on his calf.

Kahlil was looking at Strava data on his MacBook. He pulled up a run from December. “This was a big deal for me,” he said. It was his first ultra, a small 50K in Queens called the Fat Ass Trail Mix-Up. He ran well but was disqualified near the end, after inadvertently cutting part of the course. His GPS data from that day displayed 27.1 miles, in 3 hours 38 minutes—a per-mile pace of 8:04. “So it wasn’t bad,” he said.

“Strava’s really awesome,” he went on. “I love having access to all this information. Where is my heart rate? Where is my cadence?”

He navigated to Chris Vargo’s page. “I go on here and I’m like, ‘What is this guy up to?’” he said of the 2014 Way Too Cool 50K champ. “He did 11.1 miles at 8:05. OK, he’s human, you know?”

That day, Kahlil showed me a stack of photos of himself from before he went away: in sunglasses, arms crossed, standing in front of a shiny yellow sports car; surrounded by empties, looking wasted at 2 in the morning; shirtless and covered in tats, posing thuggishly and exhaling cigarette smoke. Kahlil is fond of maxims, and here he invoked one of his favorites. “I was part of the problem, not part of the solution,” he said.

He spent the first part of his childhood with his father and sister in New Rochelle. As a kid, he was smart, hyper, gregarious and charming, and often up to no good. “He was very destructive,” Omar recalls. “He liked to take things apart, chop things up, blow things up, burn things down.” Once, he brought a “Rambo knife” to show and tell.

When Kahlil was 11, he and his sister went to live with their mother, Diana Marengo, and stepfather in the Bronx. Around that age, he began drinking, smoking and stealing cigarettes. A few years later, the family left for the suburbs. Pleasantville, New York, in the mid-1990s was a small, mostly white community deep in Westchester County. Kahlil, a hyperactive Puerto Rican kid from the Bronx, got in trouble with the police for skateboarding, then illegal in town, and graffiti. In a class of suburban eighth-graders, he went around saying things like, “I know how to roll a blunt. You know how to roll a blunt?” He graduated from high school in a county jail, locked up for assault and robbery.

A few years later, after a short stint as a trainee stockbroker in Manhattan failed to pan out, Kahlil started a marijuana-delivery business called Daddy’s Magical Gardens. He gave out samples of high-quality reefer with a phone number stapled to each baggie, and waited for orders to roll in. Within a few years, he was making $10,000 a week.

It went as easy as it came, on designer belts and in clubs where he partied till 9 or 10 in the morning. As Omar recalls, Kahlil was “one of those guys that walks around with a wad of hundred-dollar bills. Used to be very annoying. He would wear these $400 shirts, $700 shoes, and he didn’t have two cents in the bank.”

“I was a total label whore,” Kahlil says. “A total materialistic freakin’ loser.”

He made the occasional attempt at legitimate enterprise—he started a dog-training business, and had ambitions as a DJ—but the money he could earn from pot was just too good. Plus, he was arrogant. Whenever friends urged him to use his business savvy in some other way, so he wouldn’t have to worry about the cops, Kahlil fired back, “Fuck the cops. It’s weed. What do I care? You’re gonna bust me? I’ll be out in an hour.”


He did get busted for drugs—four times in two years—but only on misdemeanor charges. Then, in November 2005, he was arrested for two felonies, burglary and possession of stolen property. (Kahlil says he drove the person who ended up committing the crime but only found out about it after the fact.) Out on bail the following May, he racked up five more felony charges after police searched a hotel room where he had stashed drugs and weapons. He spent a year in county jail, and, when he returned, the weed business was gone. In need of cash, he began to burglarize homes. He was arrested again in May 2008. He pled out to eight and a half years. At the time of his arrest he was 27 years old.

In 2008, while his case was pending, Kahlil arrived in Rikers Island, the large New York City jail complex known for what the New York Times recently called a “pervasive culture of violence.” Gangs were prevalent. Kahlil had joined one of the larger gangs, the Latin Kings, during a stint in juvenile hall when he was around 14. In later years, while out on the streets, he says he had little active involvement. He occasionally took a train into the city to meet up with other Kings, but mainly used the image to up his cred in Westchester.

In Rikers, it was a different matter. The Kings could offer protection and influence phone access, job assignments, even who received food.

Much of being in a prison gang was social, hanging out with the guys in the yard—until one of those guys got into a fight, at which point the group would be expected to back him up. A long-established member, Kahlil says he was “more of an advisor and a decision-maker” than an enforcer. Sometimes, he acted as a mentor or lookout for younger members who, to prove themselves, were instructed to beat or stab some enemy of the gang.

In May 2011, then in state prison at Greene Correctional Facility, Kahlil received a disciplinary citation for gang involvement and five other violations. He was sent to solitary confinement, known to prisoners as “The Box.” The United Nations Special Rapporteur on Torture has stated that, due to increasingly severe psychological effects, solitary confinement lasting more than 15 days “constitutes torture or cruel, inhuman or degrading treatment.” Kahlil’s sentence lasted nearly six months.

He was strip-searched and dressed in state-issue clothes and shoes, then marched to a small cell with a bed, a steel fold-out table, a shower and a toilet connected to a sink. Within 72 hours he received two additional pairs of underwear, up to five books chosen from his personal property, notepads and a short, flexible rubber pen too flimsy to stab with—or write with, unless wrapped in paper. Once a day, for one hour, he was allowed outside, into an adjoining “rec pen” smaller than the cell. The floor and ceiling were concrete; one side was steel grating, and three were solid walls. The other 23 hours he spent in his cell, drawing, writing, reading and trying to sleep as much as possible, to make the time go faster.

His time in The Box spanned the muggy New York summer, and the heat was stifling in the poorly ventilated cell. When a guard opened the slot to hand in mail or a meal, Kahlil rushed forward, put his face in the small gust of air and panted until the slot closed.

(In a 2015 settlement, the New York Department of Corrections agreed to a series of changes in its use of solitary, including maximum sentences for most first-time violations.)

By the time Kahlil left solitary, he felt ready to get his “shit together,” so he’d never have to go back. But, he says, “I didn’t know how I was gonna do it.”

He was transferred to another state prison, Attica, a max-security facility infamous for a 1971 riot that resulted in 43 deaths. It remained a rough place. Kahlil was familiar to some of the Kings in there. “I would tell them, ‘You know, I just did six months in The Box for this dumb gang shit,’” he says. They were unsympathetic. I’m never gonna get out of prison if I keep doing this, he thought.

After some months in Attica, Kahlil was again transferred, to Livingston Correctional Facility, in the summer of 2012. There, he focused on his case, which he was appealing. Intelligent and analytical, he had long had an interest in the law. He worked in the law library, helping other inmates with legal troubles—an in-demand practice—and took a correspondence course in paralegal research.

The rest of his energies he put toward exercising more intently than before. A natural athlete, he had learned karate and boxed in his youth, but had lately kept to the prison routine of pushups and pullups. Now, he began spending long stretches in the outdoor weight pit, pummeling the heavy bag.

Sometimes, he saw a guy jogging around the edge of the yard. One chilly day that fall, heavy rain emptied the yard of nearly everyone. Kahlil, training on the heavy bag, again saw that guy, shirtless, running laps in the downpour. OK, this guy is either fucking nuts, he thought, or on to something.

The runner’s name was Joe Murphy. Murph mostly kept to himself. His philosophy, as Kahlil described it, was, “You can run with me when you can run with me.” Those who tried never could. There was something different about Joe. “He was separate from everybody,” Kahlil says. “He had a little bit of extra freedom.”

Joe had been running for around two years before he met Kahlil. His interest had been piqued back in 2009 by a story in Outside about the ultrarunner Jenn Shelton. Soon after, he was reading profiles in Runner’s World and watching the New York City Marathon on the prison TV.

Joe was 26, overweight and addicted to pills, alcohol and nicotine. “I just realized they were doing something right,” he says, “and I was doing something clearly wrong.”

At the time, he was housed in a “gangland” max with a cramped, concrete yard. He started jogging there, a mile at a time, until he worked up to 10-mile runs. Later, after he was transferred to Livingston, he devoured books about training and structured his seasons around two annual cycles that each culminated in a goal “race.” On Livingston’s grassy .4-mile loop, Joe ran solo 50Ks and a Boston-qualifying marathon time.

Intrigued, Kahlil gave running a try. Successive knee injuries held him back for about 10 months, but during that time he worked hard to get Joe to open up. “He just kept coming around, asking about running, wanting to know more about it,” says Joe. (Joe was released in May 2015. Now 32, he lives in Queens, and at press time was training for the Vermont 100.)

By the spring of 2013, Kahlil’s knees had healed, and he started back up with short, three-mile runs.

Kahlil was driven from the start. He had always been athletic, and soon after he began regular training he tagged along with Joe for a fast mile: 6:32. He couldn’t imagine ever running faster. Then, in late June, he ended a 6.2-mile run with a 6:10 mile. Afterward, he wrote in his running journal, “Better than previous … where I was absolutely untrained; hurt like hell; but I’m not happy because I know I can do better.”

Joe was faster than Kahlil, and both were serious about training, but they found ways to run together. They’d warm up, then run easy at the same pace or break off for speed workouts as needed. One sweltering day in July, Kahlil ran 13.5 miles—33 and three-quarters laps—passing the half-marathon mark in under 1:44. The next day, he paced Joe during the last 5K of one of his prison-yard ultras: a 42-mile day, broken into three by the fragmented rec schedule. (“Sick fuck!” Kahlil wrote approvingly.)

All that summer, he got stronger. On August 2, he finished his first 20-mile run, in 2 hours 47 minutes. The next afternoon, he did two miles “easy”—7:30 pace. At 52 miles, it was his biggest training week to date.

The following week, his mileage dropped to zero after he lost rec privileges for 13 days. An officer had observed him in a group of eight inmates and, as the misbehavior report stated, “Inmate Gonzalez had been given a direct order not to be in groups larger than 6.” Still, he trained consistently into the fall.

Meanwhile, he paid lip service to the Kings. Livingston, a medium-security institution, was a “pretty casual” environment, relative to someplace like Attica, Kahlil says. Still, if he blew them off entirely, he didn’t know how they would react. The yard was the social hub of prison life, especially in the evenings, and Kahlil made a point of hanging out for a half hour or so once a week, before going for a run. Sometimes, when he went outside in the afternoon to run with Joe, he’d first walk over and greet the “bros,” so they wouldn’t feel slighted.

Some of the prison staff found Joe and Kahlil’s dedication inspiring. Officers asked them for fitness advice, or proudly spoke of finishing a 5K. Others were less supportive, and seemed to undermine the two runners in subtle, capricious ways. Prisoners could order running shoes, for instance, but the package-inspection process was arbitrary, according to Joe and Kahlil. Joe says the very same model might be approved one month, then rejected when he tried to replace it two months later. “I would spend hundreds to get one pair,” he says. “I’d probably miss three times, and then on the fourth one I’d get it.” (The Department of Corrections did not respond to questions sent via email before press time.)

Nathan Novak, another inmate at Livingston who began running in late 2013, remembers some guards moving the cones that marked how close to the fence inmates could venture so that they would be forced to cross the muckiest parts of the yard or run a circumscribed route.

At one point, the administration banned counterclockwise movement on the trail. Joe and Kahlil, who liked to switch directions with each lap, filed a grievance arguing that the prohibition increased the risk of imbalance injuries. “They laughed us out of the room,” Joe says.

Of course, those actions weren’t necessarily directed at running, or the runners, in particular. But running could get swept up in the collateral damage, with seeming indifference from the authorities. It may not have been personal, but it often felt that way.

“They really did not like seeing people find freedom in jail,” Kahlil says. “And that’s what running does.”

Kahlil Gonzalez running one of his go-to New Rochelle loops, the Leatherstocking Trail.
Kahlil running one of his go-to New Rochelle loops, the Leatherstocking Trail.

One day in the yard, Kahlil felt too sore to run, so he borrowed a measuring wheel from the rec staff and pushed it around outside. He sketched a map of the yard, annotated with distances that he could reference for interval workouts, and wrote “Running Pattern” across the top.

About a month later, on June 14, 2014, a corrections officer saw Kahlil with “multiple small laceration[s] … on the face and neck” and a “swollen and red” left eye, according to a misbehavior report. Because the injuries were “consistent with being in a fight” and Kahlil had not reported them to staff, he was written up for fighting, “violent conduct” and failure to report an injury. He was sent to solitary. (Kahlil says the injuries were insignificant and likely from working out. The misbehavior report contained no further evidence of fighting or violent conduct.) A day later, a search of Kahlil’s dorm space turned up the map, which an officer deemed “escape paraphernalia.”

It was a grave allegation, one that could end up before a criminal court. Kahlil, with his DIY legal education, was convinced the charge was frivolous. Still, he was worried. Disciplinary hearings in New York State prisons lack the impartiality and evidentiary standards of courtroom trials. According to a 2012 report by the New York Civil Liberties Union, they “often boil down to the testimony of a corrections officer against that of a prisoner.”

As he awaited the hearing in his isolation cell, Kahlil penned a 14-page brief in his defense, full of procedural and substantive objections and case-law citations. “[T]he cold reality that I’m sitting before an arbitrator, pleading my defense for anything remotely having to do with the word ‘escape’ is literally terrifying,” he wrote.

Kahlil was lucky. His hearing officer was fair, and found him not guilty of the escape charge. Even so, he was convicted of a lesser violation, “contraband,” for possessing “a map of the yard which he was not approved to have by staff,” as the hearing disposition stated.

The fighting and unreported illness charges—he was acquitted of violent conduct—had resulted in a 30-day sentence to The Box, which he was two weeks into. The contraband conviction added 11 more. The guards knew how avidly he ran and, Kahlil says, some of them taunted him: “Yeah, you’re running now, huh?” “How’s that 5K going in there?”

In fact, he was running. Back in December, while recovering from shin splints, Kahlil had written in his running journal, “Blank pages result in depression and mild psychosis!” As long as he was healthy, he would keep going—even when that meant running in the “dog kennel” that was the solitary-confinement recreation pen. He rolled up the cuffs of his state-issue pants, removed his state-issue shoes—laceless and loose, they just flopped around—and ran 20-foot laps, barefoot, on the concrete floor.

The laps were so small they made him dizzy. The awkward inward lean stressed the muscles in his feet. The hard surface grated at his soles until they turned as rough as bark. At first, he could only manage an hour every two or three days, but after two weeks he began to adjust. His feet grew stronger and girded in calluses. In mid-July, he ran four consecutive days. That beat his feet to pulp, but this time he needed only one day to recover. Accelerating was nearly impossible, so to up the effort he tried breathing exercises, syncing inhalations and exhalations with progressively longer sets of strides.

He was back in the yard on July 28, and ran five miles in a downpour.

Thirteen months later, after Omar met Kahlil on the day of his release, their first stop was the parole office. Next, they checked in at the homeless shelter where Kahlil would spend his first few nights of freedom. (For legal reasons, parole had not approved him staying at his father’s address.) The shelter was in a large, ugly basement room. It was dirtier than the prisons he had been in. Kahlil was given blankets and told to find a spot on the floor. He didn’t have time to run before his curfew that night. Distrustful, surrounded by junkies and people who looked sick, he passed a sleepless night in a folding chair.


The next morning, he took a train to his dad’s place in nearby Mount Vernon and scanned for patches of green space on the computer, then left for a run. He found a paved trail with weeds growing out of the cracks that continued for  less than a mile before dead-ending in a highway. Kahlil ran along the shoulder for a quarter-mile, until the next exit ramp, then took roads back to his father’s. “It was awesome,” he says. He had run about six miles; later that day, he went out for another three.

A few days later, he moved into a halfway house in New Rochelle and, soon after, began his job at the law firm. He got the interview—the only interview he got out of the dozens of places he applied to—because an inmate he had helped with a legal issue in prison knew one of the firm’s partners.

Few people outside of family had written Kahlil after he was incarcerated. He had been an unethical businessman as well as an illegal one, ripping off suppliers; and he alienated his more responsible friends by squandering his talents on clubbing and drugs. His first letters to his father were filled with rage and demands that Omar describes as “emotional blackmail.”

Midway through his sentence, Kahlil’s tone became more sensitive and centered. “It seemed like the anger in his letters was fading,” Omar says. “I guess he was releasing his emotions through running.” In an April 2015 inmate progress report, his law-library supervisor noted that Kahlil was “a very knowledgeable, conscientious, energetic and dedicated Law Clerk.” “His whole persona, demeanor, has changed, has become so positive,” says Diana, his mother.

After his release, Kahlil sent out some 200 apologies over Facebook to people from his past. The messages rekindled a few old friendships and led to at least one new one, with a woman he says once hated him and now talks about races they can run together.

“It’s good to have friends,” he says. “It’s something I’m not familiar with from before. Everybody who was around me was very superficial, probably around me because I always had access to good parties, good drugs, good times.”

Kahlil’s athletic ambitions and career goals substantially overlap. The 35 to 50 weekly miles he was running when I visited were less than he would have liked, but all he could manage between working and commuting. He hopes to someday make a living from a constellation of independent ventures, some of them running related—coaching, maybe, or directing a suite of races in Westchester, where the extensive trail system has yet to host an ultra. He’s considering a move out west in three or four years, when his parole is up, to a state like Colorado or Arizona that has big, rugged peaks and the mountain races to match.

Kahlil Gonzalez on a section of the Leatherstocking Trail.
Kahlil on a section of the Leatherstocking Trail.

One Saturday afternoon in April, I joined Kahlil for a trail run in New Rochelle. He wore sunglasses and a black muscle shirt that exposed tattoo-drenched arms. The trail began in a quiet neighborhood, and dipped slightly as it entered the woods. Shoots of green had appeared on the branches, but had yet to overpower the browns and grays of fall. Spring had sprung, tentatively.

The week of his release, this had been the site of his first true trail run. The path was wide and mostly smooth, and the climbs and descents slight, but compared to the prison yard it had been tough. “Those little rolling hills are nothing now,” he says, “but they kicked my butt.”

Kahlil has a 10 p.m. curfew. He cannot drink alcohol, or “frequent” bars. He must report any police contact, positive or negative, and is subjected to regular urinalysis. He needs permission to leave the state, including when he visits his grandmother in Connecticut. But if the hardships of life as a felon bother him, he gives little indication. “I’m working in Brooklyn,” he says. “I travel two hours away from my house, for 12 dollars and 50 cents. I live in a little room, I don’t have a girlfriend, and I’m happier than I’ve ever been in my life. So yeah, I wouldn’t change anything.”

As we ran past a pond and headed for a highway underpass, Kahlil kept up a steady commentary: on features of the trail, on local runners he admires, on a mile-long Strava segment for which he held the fourth-fastest time. He said he couldn’t ever see himself racing as frequently as some runners do. More racing means more tapering, more tapering means less running and running, to him, means peace, medication, salvation, freedom.

He ran with precise, mechanical form: short stride, slight forward lean, arms militarily compact. On the occasional technical sections, he seemed to speed up. Later that afternoon, he would tell me that even then, eight months on, a wooded trail could still amaze. “I stop and take it in sometimes: ‘Look at that. No barbed-wire fences, no arrogant inmates,’” he said. “That hasn’t diminished.”

Paul Cuno-Booth is the associate editor of Trail Runner.

This article originally appeared in our September 2016 issue.

Want to Know What It Takes to Finish at Western States? Just Ask Hellah Sidibe.

Find out what happened when this six-year run streaker and HOKA Global Athlete Ambassador took on an iconic ultramarathon in California's Sierra Nevada