Baltimore Jack was dead. In a place where even the speediest travel slowly, the word spread up and down the length of the Appalachian Trail from Georgia to Maine in a matter of hours. It was May 4, 2016, and one of the most beloved, brilliant, and exasperating antiheroes in the history of long-distance walking was gone.

He was 57, and it was the beginning of his 21st year on the trail. Over that time, he had become a sort of everywhere-at-once presence, bandages wrapped around his battered knees, relying on snack cakes, lasagna, Jim Beam, cigarettes, and the kindness of others to survive. It was a kindness he usually returned.

His first year on the trail was in 1995. He would eventually thru-hike the AT seven times. In 2003, after eight years of walking with what was—according to nearly everyone who encountered him—a heavy pack, Jack’s knees gave out. But even without being able to travel great distances on foot, he stayed on the trail. For the next 13 years, Jack flowed northward, catching rides or sometimes walking for a few miles with other hikers, following them from hostel to hostel, town to town, cooking them meals—his Thanksgiving feasts were legendary—rescuing them, and becoming the trail’s most comprehensive repository of wild yarns and unyielding opinion.

Everybody on the trail knew of him, yet very few people truly knew him. He authored over 10,000 posts on the influential White Blaze forum, an online clearinghouse for AT information named after the color of the symbols that mark the trail, and published an indispensable online guide on how to resupply en route. But his real name, his past? The tales of his exploits sometimes seemed to stretch as tall as the trees in the eastern forests he’d made his home.

The best folks could do was piece his story together via his trail name. Baltimore Jack took his handle from the first line of “Hungry Heart,” Bruce Springsteen’s 1980 hit song: Got a wife and kids in Baltimore, Jack / I went out for a ride, and I never went back.

The legend was that Jack had done the same, leaving a family for a life on foot that rejected convention, while seeking a higher truth along a dirt ribbon that winds through thousands of miles of forests, hills, meadows, and mountains.

I didn’t know him as Baltimore Jack. I was at Hampshire College in Amherst, Massachusetts, with him from 1979 to 1983, where I called him by his given name, Adam Tarlin. We worked on the school newspaper together, me as the editor, Adam as a writer. He was four years older than me—at Hampshire, an experimental institution founded in the 1960s, it wasn’t unusual for a student to stay for years—and one of the most interesting people at school. I would go so far as to call him a genius, but we clashed a lot, mostly over my edits of his contributions to the paper. Adam’s writing style was eviscerating but in a special way: you could see his passion and you liked him, even as he cut you down.

When I graduated in 1983, it was a rainy day, and I remember seeing Adam outside the auditorium in his usual dark trench coat. He shook my hand, and I never encountered him again. I never learned that in a year, he’d be married. That he’d have a daughter. That he’d leave soon after that. That he’d struggle for a decade, only to resurface one day at a trailhead in Springer Mountain, Georgia—the AT’s southern terminus—and sign “Baltimore Jack” to the register.

I’d heard about Baltimore Jack from a close friend who had walked the AT a number of times. It was only after Jack’s death, in a strange coincidence, that I learned through my college alumni magazine that Baltimore Jack and Adam Tarlin were the same person. The information came in the form of an obituary.

Some pre-Jack friends saw Adam as irresponsible, a person who’d abandoned his family to indulge himself. But many of the friends who only knew him as Baltimore Jack viewed him as noble, somebody who’d done what he had to do to save his own life, whose philosophy could be summed up with a story he told a television-news interviewer in 1998, just as he was about to reach the 5,269-foot summit of Mount Katahdin, the AT’s end point in Maine. Jack was talking about an encounter he’d had with a gentleman who’d never heard of thru-hiking. The man had peppered Jack with questions about logistics, mileage, and bear attacks, then finished up with a more basic query: “What do you do in the real world?” Jack’s reply: “In the real world, I hike.”

Jack would stay on the trail all season, working odd jobs, sleeping where he could. In winter he’d return to a small shack in New Hampshire—he liked the state’s independence and proximity to the woods—where he’d brave the cold and save the little money he earned as a convenience-store cashier for next year’s walk. After retiring as a thru-hiker, Jack’s physique changed from the can’t-get-enough-calories frame of a long-distance athlete to, by the end, somebody who looked tired and overserved. By 2015, his trail friends, as well as a few who’d resurfaced from his previous life, were urging him to seek medical help. He never did.

One of those friends, Bob Peoples, who owns the Kincora Hiking Hostel in Hampton, Tennessee, says, “I asked him to slow down, to get help.” Peoples is a former Air Force officer, and when we spoke, his tone was reserved and factual. But as he reminisced about Jack and his declining health—the drinking, the weight gain, and an obvious sense that he was unwell—his voice softened. “I said, ‘Jack, this is going to kill you.’ And he looked up.”

Peoples paused. “Do you want to know what he said? His answer was: ‘So?’”

It was a grim hint at what would happen two years later, when Baltimore Jack collapsed at a thru-hiker hostel in Frankin, North Carolina. (The hostel has since been renamed in Jack’s memory.) He was rushed to the nearest hospital. The cause of death was suspected to be a pulmonary embolism.

“One fine day in my thirties,” Baltimore Jack told the Pox and Puss thru-hiking podcast in 2013, “I decided I wanted to hike.”

Jack didn’t mind letting people assume he came from the Maryland city. Had he been in the military, as evidenced by the dog tags he wore? “He never claimed to be, but if it added to his mystery, people could think what they wanted to,” says Michael Sisemore, a former Army Ranger who walked with Jack on his 1999 hike and lived with him the following three off-seasons. Had he held a high-powered job as a media executive or newspaper reporter before dropping out and onto the trail? No, but he did work the counter at a video store in Boston, where he was well loved by customers for his obsessively deep knowledge of film, the same way he’d ultimately be regarded for his trail expertise. Did he really discover a dead body in a flophouse turned hostel in Pennsylvania? Yes, but the story has been repeated so often by other hikers that it’s hard to know which version is accurate.

In college, we called him Adam. His full name was Leonard Adam Tarlin. The name Leonard came from his father, who Adam often described as Harvard faculty. (He wasn’t; he worked as a department-store buyer most of his life but by all accounts possessed a formidable intellect.) In the years between college and hiking, almost as if he was working toward abandonment of his birth persona, it appears that Adam began referring to himself as L.A. Tarlin, then Baltimore Jack Tarlin, and finally, to most, just Baltimore Jack.

One of the stories repeated in college was that Adam’s volatility, and possibly his drinking, was the result of losing both parents in a car accident when he was very young. It wasn’t true. The reality, though, was painful enough. His mother, Jeanne, died of cancer when Adam was nine. Adam had three sisters. Erika was two years older than him, and the other two were in their late teens when their mother was stricken. That left his father to raise the children alone, as an overwhelming sadness settled over their Brookline, Massachusetts, home. “Our childhood was smashed,” Erika told me when I met her last year in Boston. “We didn’t have anything to look back at with nostalgia even, because it all just felt sad.”

Adam transformed from a cheerful student to a teen who didn’t mind receiving poor grades in classes that didn’t interest him. Happy moments with family felt rare, Erika says, but what existed often centered around hiking. The Tarlins explored the forests of New England. Those explorations led his father to promise his son that one day the two of them would walk the Appalachian Trail. It didn’t happen. Just before Adam’s high school graduation, his father died of a heart attack.

The Appalachian Trail was a very different place in 1995, the year Baltimore Jack first set out. The route was more sparsely used, a rugged thoroughfare stretching an intimidating distance.

For the first four decades of the AT’s existence, the idea of traveling it all in one season remained obscure. Up until the 1980s, about 20 people did it each year. Those numbers rose significantly during the 1990s, but the trail’s emergence as a pop-culture bucket-list item became a thing in 1998. That was the year Bill Bryson’s A Walk in the Woods appeared. Though Bryson and his hapless buddy never completed their hike, the idea of an end-to-end epic gained public traction, and the number of annual completions has grown steadily ever since, reaching beyond 1,000 (out of more than 3,000 attempts each year). Three million people walk some portion of the route each year, according to the Appalachian Trail Conservancy.

Bryson’s take on thru-hiking made it seem like a jaunt. A more relevant reference for Jack is Cheryl Strayed’s 2012 memoir Wild, which chronicles her 1995 attempt on the Pacific Crest Trail. Wild represents what has always been a powerful motivation for on-foot completionists: redemption. In the tradition of Earl Shaffer—who in 1948 was the first person to complete the AT, walking it to escape memories of World War II—Strayed tackled the PCT after the death of her mother, a divorce, and a descent toward drug addiction. “The hike,” she told Vogue in 2012, “was a really great chance for me to think through every aspect of my life.”

On some level, the tediousness of walking from dawn to dusk makes the crucible of self-reflection inevitable, even as the AT and other long-distance trails attract idealists, drifters, and the occasional unstable or homeless person with no other place to go—or at least no seemingly better place to go. On a do-it-yourself, 200-mile foot journey across Australia’s Nullarbor Plain in 2010, I couldn’t avoid exploring my own dark places. One of the first people I met said to me, “You must have something to atone for.” He was right; I’d hurt somebody badly, destroying something important to them.

“Most people show up on the trail when they’re in transition,” says Lawton Grinter, one of Jack’s friends and a three-time AT finisher. “You’re trying to become the person you always wanted to be.”

After his father’s death, Adam often landed at the doorstep of a classmate, Elaine Kaplan. She lived in a house on the other side of town from the Tarlins’ apartment. “With his parents gone, he spent a lot of time with us,” says Kaplan, now an educational administrator in Cincinnati. And there was something special about Adam. “We wanted to take care of him,” she recalls.

Adam soon confessed his life’s dream to Elaine. It had nothing to do with the outdoors. “He was going to live in England,” she says. Adam had a passion for British history. But there was also something troubling: how the most fun and lighthearted conversations and moments Elaine had with Adam, who would become her boyfriend by their senior year of high school, occurred when Adam was drinking. “He was the only teenager I ever knew who carried a flask,” Elaine says. “I think drinking was his way of coping.”

When Elaine was accepted to Amherst College, Adam chose to attend Hampshire College, just a few miles down the road. The educational institutions couldn’t be more different. Amherst is steeped in tradition. Hampshire is an educational experiment—independent study and no grades—where students are sometimes described as underachievers. (I had that box checked by high school guidance counselors.)

As the school newspaper’s editor, I remember often being fed up by Adam’s argumentative nature, his cruel barbs, and his gleeful willingness to play the villain. I also remember that it was hard to stay mad at Adam. His intelligence and charisma always lured you back.

Those qualities were especially on display with women. At a college where tie-dye was considered couture, Adam set himself apart in dark glasses, a leather jacket, and black leather gloves. He stood almost six feet tall, with strong features and a mane of tight brown curls. “He was good-looking and charming,” Elaine says. “There was a lot to like.”

By their sophomore year, Adam and Elaine had broken up. Adam stayed platonically close to Elaine’s roommate, Sharon Miller. Adam’s friendship with Miller became one of the few that threaded into the Baltimore Jack era, and she was one of the people to whom Adam could expose his deep sense of loss. “He never really got over it—his parents, Elaine,” says Sharon, who now lives near Albany, New York, and works as a psychotherapist.

“Most people show up on the trail when they’re in transition,” says Lawton Grinter, one of Jack’s friends and a three-time AT finisher. “You’re trying to become the person you always wanted to be.”

As college ended, Adam and I had a falling out over the school paper. In 1982, he dropped out of school, just as I was entering my senior year. I was living off campus in Northampton, and I’d often see Adam at Packard’s, the town’s primary watering hole.

One of that year’s biggest media events was a made-for-TV special called The Day After, a docudrama about the horrors that would befall America after a Soviet nuclear strike. There were viewing parties everywhere, and Adam showed up to one on the Smith College campus, at the west end of town.

A graduate student named Allegra Brelsford noticed him, and after the movie ended, the two went for a walk. “We hit it off,” says Allegra, now a well-regarded artist based in New York City who specializes in making quilts. “He was smart and good-looking, and he did The New York Times crossword puzzle in pen.”

The couple married in June 1984 and had a daughter, Jillian, in January 1985. Allegra was finishing graduate school. Adam wasn’t working and was still drinking. Though he clearly loved his daughter—Allegra told me how tenderly Adam held his infant child—the family split up within a year. “After that,” Allegra says, “he lost touch very quickly.” In the coming years, Adam would make occasional attempts to contact his daughter for key life events. He hitchhiked off the trail to attend Jillian’s high school graduation party. In late 1989, Allegra remarried, and for all practical purposes, her current husband—they have a son as well—has acted as Jillian’s father.

Allegra says that she has no ill will toward Adam: “He had all these things he did in order to have an identity, but no matter what, there was that vulnerability, his heart. It was hard to be angry.”

As for Baltimore Jack, he didn’t see his exit as an exact analog for the lyric that inspired it. “[The song] would lead people to think that I walked out on my wife and kid, which I can assure you is not the case,” Adam said in the Pox and Puss podcast. “No,” Adam continued. “She walked out on me for ten thousand excellent reasons.”

“I’ve led the type of life that does not discourage outrageous storytelling,” Baltimore Jack told Pox and Puss. That’s basically true, but there’s a huge gap—between the end of his marriage and his appearance on the Appalachian Trail a decade later—where it is hard to determine what Adam was doing. One of our mutual classmates is a woman named Leslie Magson. She grew up with Adam, attending the same high school, and postcollege she rented Adam a room in her Beacon Hill apartment. Adam was working as a clerk at the gigantic Tower Records store in Boston, where he became well-known for his spot-on movie recommendations. Despite being employed, he fell behind in the rent.

Several months in arrears, Leslie and Adam had a confrontation in the lobby of the music shop. A few hours later, Adam showed up with money and Leslie evicted him. What did Adam take away from the incident? Based on his actions and the nomadic lifestyle he began adopting after that, one thing seems likely: Adam decided he’d never pay rent again.

By the 1990s, Adam was living in Hanover, New Hampshire. The town is significant for being the home of Dartmouth College, for having a major nearby medical center, and for the Appalachian Trail, which hits Hanover at mile 1,748. Adam’s reason for living there, he told one friend, was that it had the best library on the trail.

There’s no specific incident that documents why Adam decided to go walking. But there’s no doubt he encountered thru-hikers in Hanover. He worked at Stinson’s, a small convenience store in town. The job provided just enough to live on, so Adam found a bed in a ramshackle cabin on a wooded, 38-acre property owned by a carpenter named David Vincelette. It was a short walk from town, and if you’re going from Stinson’s to Vincelette’s, just after you pass the local food co-op, you’re actually hiking a section of the AT.

Did seeing the trail give Adam a daily reminder of his father’s promise? I like to believe that it did, but I’m not so certain that Adam’s initial attempt to walk the route falls neatly into the self-transformative Cheryl Strayed model. I think his foray into thru-hiking may have been a result of need. After a year, Vincelette didn’t charge Adam rent; instead, payment came in the form of chopping wood. “I didn’t see him as a worker,” Vincelette, who still lives in Hanover, told me. “I saw him as a talker. But he ended up being both. He’d educate me on European history, and I’d educate him on how to cut a board.”

With his limited funds, Adam must have realized he’d be better off saving paid-for lodging until winter, when it would really be necessary. In the summer, he didn’t need a roof over his head. In April 1995, Adam thumbed a series of rides along Interstate 95, finally arriving in Georgia, where he made his way to the southern end of the Appalachian Trail. With his father’s dog tags around his neck, carrying a 60-pound backpack, Adam Tarlin stepped onto the footpath—and into a new self.

The basic outlines of Baltimore Jack emerged very quickly that year. His pack became notorious, the heaviest items in it books—he’d never lighten them by tearing pages out—along with liquids: “He’d always send himself several bottles of Jim Beam so they’d be waiting for him at resupplies,” says Wayne Lummis, who walked part of the trail with Jack in 1995.

Lummis describes Jack as admirably true to the spirit of thru-hiking: “Sometimes I’d see him, and he’d be covered in bruises, because he insisted on rigorously following the white blazes. If that meant crawling under a fallen tree, he’d do it.”

All that determination, though, didn’t lead to a complete thru-hike in 1995. As Jack approached the trail’s homestretch—Maine’s Hundred Mile Wilderness, which leads to the summit of Mount Katahdin—he was injured in a fall. He limped back to Hanover, healed up, and spent the winter bagging groceries.

Adam Tarlin always found a way to fascinate women and evoke a genuine protective instinct in them. It made sense. He’d lost his mother early, so figuring out how to receive the nurturing he’d missed was an essential skill. I’d see it when Adam met girls at college parties: he’d listen intensely, fixing his gaze to theirs, instead of just trying to hook up. The women who loved Jack, platonically or romantically, truly loved him. There’s nobody who represents that friendship better than Jen Whitcomb.

It was late fall of 1996. Jack, who was 38 years old at the time, had spent the summer working at Bascom Lodge, off the AT near Williamstown, Massachusetts. It was an early preview of his post-hiking life—he loved to help, according to his friend Andy Somers, who had hiked in 1995 with him—and as the season ended, Jack completed the Maine section he’d missed the previous year, getting credit for a section hike. Back in Hanover, he was living with other tenants at Vincelette’s place, and the weather was getting cold. Whitcomb was 18 years old, 20 years younger than Jack, and had just entered Dartmouth.

It was a great school, but at first it didn’t feel like a good fit for her. Whitcomb had just graduated from a pressure-cooker high school in Virginia and was struggling to balance a heavy class load and a part-time job during her first term. “I realized I needed to hit the brakes on academics and take a different challenge,” she tells me. The AT’s white blazes were a block from her dorm.

As she spoke to her friends about a hike, one piece of advice kept coming up: talk to Baltimore Jack. “Everybody said he knew everything about the trail,” Whitcomb recalls, “so I approached him at a coffee shop and said, ‘I want to go hiking.’”

“I can help you,” he told Whitcomb, sweeping aside a pile of library books and offering her a seat. Over the next two months, the two planned their separate 1997 hikes. Whitcomb set out on the trail that March, a couple of weeks before Jack. He caught up with her in Hot Springs, North Carolina, as she rested there with a sprained foot. They spent the next 1,000 miles trekking within a day of each other. “He had a very detailed knowledge of the trail, told great stories, and threw insults better than anyone I’d ever heard,” Whitcomb recalls.

On August 20 of that year, signing off with the transitional moniker L.A. “Jack” Tarlin, he reached Katahdin. Whitcomb had finished her walk just before reenrolling at Dartmouth. Jack, without a place to stay, and Whitcomb, by now used to a lifestyle of crowded shelters and dirtbagging, had no hesitation about inviting her friend to live in her dorm room. “I put my bed up on cinder blocks, and he slept underneath,” Whitcomb says. “I know it was weird to have an almost 40-year-old man bunking below me, but he was never inappropriate. He looked out for me, and occasionally bought booze for the other kids on my floor, and helped them with their history papers.”

Over and over again, I heard how kind and caring Jack was, especially toward young women. I asked Whitcomb if she thought Jack was trying to compensate for not being present to raise his biological daughter. “He was always showing me pictures of Jillian,” Whitcomb says. “And then he’d say, ‘I’ve got a perfect daughter in Vermont who I’m not fit to raise. She has a better father now.’”

Whitcomb graduated from Dartmouth, joined the Coast Guard, and moved to the West Coast, where she’d eventually start a family. Jack returned to the trail. As the new millennium dawned, he settled into a persona that he’d more or less hold to for the rest of his life. Baltimore Jack was a happier, more purposeful version of Adam, but he was still capable of making friends and enemies.

On the White Blaze forums, posting under the username Jack Tarlin, he recommended Walking with Spring, Earl Shaffer’s account of his pioneering 1948 thru-hike. Shaffer, like Jack, was a romantic.

When he was actually walking, Baltimore Jack’s stories seemed to swing from the outrageous—like the dead body he found at the Doyle Hotel in Pennsylvania, whose cheap rooms and beer made it a thru-hiking landmark—to genuine heroics, like the time he gently carried a hiker with a broken leg a mile and a half to safety, waiting for an ambulance when they finally reached the road, then quickly disappearing back into the woods.

Part of Jack’s mission, it seems, was to deflate those who wanted to make the trail so sacred—or worse, so athletic—that ordinary folks would feel excluded. To a White Blaze commenter who questioned the nutritional value of Pop-Tarts as trail food, Jack countered: “Pop Tarts are a perfectly sensible thing for folks to eat at breakfast time.” Jack recommended at least four per meal. He began keeping what was, for almost a decade, an essential trail reference. Posted annually on White Blaze, “Jack’s Resupply Guide” was, in the days before smartphones, a voluminous survival handbook, listing everything from guesthouses to post offices to taverns. It was written in Jack’s particular prose style, with a clear nod to his “keep it fun” outlook: “This is NOT intended to be a blue-print, framework, or manual for anyone to plan their hike by,” says the guide’s introduction. “There is no one ‘right’ way to hike the A.T….no one ‘right’ way to re-supply yourself. Something like 9,500 men and women have hiked the A.T. in its entirety, and no two have done it the same way. It’d be presumptuous in the extreme for anyone to claim that there’s only one way to plan or execute your hike. There isn’t.” Jack’s downloadable guide was free. His only attempt to profit from the trail was to sell T-shirts emblazoned with the phrase “Bill Bryson Is a Candy Ass.” Those who’ve seen his annotated version of A Walk in the Woods—it went missing after Jack’s death—say that it’s a hilariously devastating companion to the book.

As common sense as his outlook seems, it contained a hidden subtext—it was an attack on those who took the trail too seriously, who appointed themselves gatekeepers. Among these, in Jack’s view, was another trail legend, Warren Doyle.

Doyle, 69, has walked the entire trail 18 times, nine of them as a thru-hiker. He currently runs what amounts to a long-distance-walking training facility in Mountain City, Tennessee. Study with the Appalachian Trail Institute, Doyle says, and your chances of completing a thru-hike increase from under 25 percent to over 75 percent.

Doyle’s disciplined approach rankled Jack, and Jack’s party-on-foot demeanor sat poorly with Doyle. Such philosophical conflicts aren’t unusual. But the fight between Jack and Doyle got personal. “They were bitter enemies,” says Bill O’Brien, former president of the Appalachian Long Distance Hiker’s Association, a group Doyle founded.

When I spoke to Doyle, he lumped Baltimore Jack with several others, including Cheryl Strayed, who seek the trail as a means of healing. “It’s something I wish wouldn’t happen,” Doyle told me, “People love train wrecks.” (Doyle’s objection, he says, is that such people get “an inappropriate amount of publicity.”)

Doyle also holds Jack responsible for the emergence of a sort of clannishness on the trail—Jack’s tribe was a loose group of a few dozen buddies called Billville, after a name embroidered on a thrift-shop shirt that one of the hikers wore—that he says is the real source of exclusionary attitudes and division on today’s AT and far from being an advocate of “hike your own hike.” Despite that mutual enmity, it seems to me that Doyle and Jack, who met a few times over the years, agreed on more than they thought. Both are literary minded. Both saw the trail as something more than just a walking route. Both viewed it with a respect and an intensity so extensive that, in full circle, the two end up occupying the same role: defenders of hiking’s most celestial institution.

One of the most repeated depictions of Jack involves his knees. He’d appear on the trail wrapped in filthy bandages, as if he were emerging from an accursed sarcophagus. Early on, Jack was a strong hiker, capable of 20 miles a day with his massive pack, but by 2003, after his final thru-hike, his knees were bad enough that he could no longer walk great distances. He still looked physically healthy—he was trim and muscular, with his body showing no outward effects of drinking and smoking—but he was ready to abandon the idea of fully completing the trail every time. In February 2003, Jack announced on the White Blaze forum that for the upcoming season, he’d be on the trail in a different capacity: “Hope to get some trail work done,” he wrote. There’d be a little walking: Jack would go “as far as I feel like.” How far? “It’s anyone’s guess,” he concluded.

You’ve probably heard the term trail angel. That’s a person who isn’t hiking themselves but who provides a service, usually as a volunteer and sometimes for a donation. That might mean somebody who gives a hiker a lift to a hostel down the road, or cooks up a trailside meal, or routinely offers a reliable source of water or a place to retrieve packages. In recent years, some trail angels have formalized their roles; among the most famous is Janet “Miss Janet” Hensley, who offers hiker shuttles up and down the AT. (Hensley and Jack were close, according to nearly everyone I spoke to; I reached out to her for comment on this story but was never able to connect.)

Baltimore Jack’s stories seemed to swing from the outrageous—like the dead body he found at the Doyle Hotel in Pennsylvania—to genuine heroics, like the time he gently carried a hiker with a broken leg a mile and a half to safety.

Jack’s support as a trail angel quickly became as notable as his hiking. Following the wave of hikers heading north, Jack would plant himself for a bit at one hostel, then the next. He gained fame for his lasagna suppers, which he’d cook for dozens at a time. Ironically, for somebody known as a heavy-pack enthusiast, he was also in demand for shakedowns, an aggressive culling of newcomers’ overly laden loads. More than that, by actually living on the trail, Jack became, arguably, something unique: a hobo ambassador who was the AT’s living, breathing, ambulating encyclopedia.

One of the places where Jack spent the most time was the Kincora Hiking Hostel, near Hampton, Tennessee. Owner Bob Peoples had completed a section of the trail once and found the experience so meaningful that he devoted his retirement to serving hikers. The latter-day Jack became a Kincora fixture. “He’d clean, he’d cook, he’d entertain a mob,” Peoples says.

Peoples has a different insight into Jack’s world, because he also acted as his financial adviser. Occasionally, there’d be a tax refund or paycheck for Leonard Adam Tarlin. The problem was that Jack was no longer L.A. Tarlin. “He had no bank account and no ID,” says Peoples. So Jack signed over his checks to Peoples, who deposited them and then doled out the money to him over the winter: “It was a budgeting thing, too. He’d have spent it all, otherwise.”

“On what?” I asked.

“He’d have given it to other hikers,” Peoples says.

Such saintly behavior aside, one part of Jack that was becoming less sanctified was his body. Thru-hiking had masked how unhealthy he actually was. Now Jack began to put on weight, a process that accelerated after he quit smoking.

Photos of Baltimore Jack starting in the late 2000s show a person who is unrecognizable from the handsome, slick Adam I knew. But Jack made the change part of his legend; strangers began to offer tributes of whiskey and Little Debbie snack cakes, bringing them directly to Jack or leaving them on the trail with notes. There was a cultish aspect to the hero worship. Suddenly, Jack was infallible. True friends saw Jack as he was and tried to help him. But they were in the minority.

At the start of this decade, the worlds of Adam Tarlin and Baltimore Jack suddenly collided. That’s because old friends began finding him, as old friends do, on the internet. What they saw was astonishing. “I’d lost touch with Adam over the years,” says college friend T.J. Mertz. But a search of Appalachian Trail message boards led Mertz to Adam, who by then had become Baltimore Jack.

“I can see that he was able to find a place where he was free, where he was able to rely on his wits and his intelligence. But he also didn’t take responsibility, and I’m not trying to be judgmental—part of me, sitting here with a mortgage and two kids, admires what he did—but I want to ask: Was what he did incredibly selfish?”

Those who only knew Baltimore Jack were also asking questions. Jen Whitcomb, stationed in Seattle with the Coast Guard, was trying to get Jack to admit he needed help. At one point, she even offered to marry him, on paper, so he could get health insurance. Jack’s reply: “I can’t do that to you.” When Whitcomb got married herself in 2012, she called up and down the trail to locate Jack and invite him. She offered to buy him an airline ticket. But Jack had no identification, so he couldn’t travel. Instead, Jack posted a picture from Whitcomb’s wedding on Facebook; in it, the bride and groom are ecstatic. Jack’s caption: “Just wanted to share a photo from a recently married friend. Some of you may remember Jen Whitcomb, Yahoola, A.T. 1997, the greatest woman hiker of all time!”

But Whitcomb didn’t want praise from Jack. She wanted him to get better.

“It was hard to see him wasting away,” she says. “He was visibly declining.”

Whitcomb found herself thinking the unthinkable. “I remember telling a friend,” she recalls, “that if he dies, I hope he drops on the trail. Wasting away in the hospital would kill him twice.”

There was one final, near miss effort to help Jack clean up. It came through his old friend Sharon Miller. Her view of Adam was probably more realistic than what others saw.

“He was, essentially, homeless,” Miller says. “And he owned that. He told me that he didn’t stay on the trail for some noble reason, but because people took care of him. ‘They feed me,’” she recalled him saying. “‘I don’t have money for food.’”

Miller says she wanted Jack to sober up. She bought him a T-shirt that not-so-subtly encouraged him to embrace who he really was; it was emblazoned with a palindrome: “MADAM, I’M ADAM.”

In 2009, Miller tried to get Adam enrolled in health insurance under New Hampshire Medicaid. The plan was to get Adam sober, likely in an inpatient program, and to get his knees fixed. But Adam was unable to sign up for the insurance, and when the 2010 hiking season began, he headed south. It was the last time Miller would see him. For the next six seasons, Baltimore Jack held court on the trail. He told stories. He gave advice. He drank.

And then he died.

On the morning of May 4, 2016, Jack was volunteering at a thru-hiker hostel in Franklin, North Carolina. He’d complained to staff that he felt out of sorts, and finally agreed to go to the hospital. He was immediately sent to the ICU, where he died the next day.

Soon, the White Blaze forum and social media were overflowing with messages of condolence, grief, and disbelief.

Erika Tarlin, who hadn’t seen her brother in a few years, learned of Adam’s passing via her niece, who’d seen the news on Facebook: “I got a frantic call from my sister’s daughter, who’d seen the post. She said to me, ‘Uncle Adam is dead.’”

The same scenario repeated for dozens of others. Sisemore, Vincelette, Mertz, and Whitcomb all learned that their friend was dead via social media. “I was scrolling one morning,” Whitcomb says. “It had happened just a few hours earlier. I couldn’t believe it.”

By then, Whitcomb had two small children. She says, “That was the first time they saw me cry.”

Erika Tarlin has a question. “I understand that he became Baltimore Jack,” she said. “But what I can’t understand is why that meant making Adam disappear.”

The closest anyone has gotten to that answer came in 2016, when the annual Appalachian Long Distance Hikers Association gathering was held in Williamstown, Massachusetts. It turned into a large celebration and remembrance of Baltimore Jack.

A controversy arose amid the online eulogies. Adam’s friends and Jack’s friends saw things in fundamentally different ways. Some of the former viewed Adam mostly as somebody who’d hurt others and squandered his potential. The latter held Jack up as somebody who’d broken the shackles of convention and found transcendence in nature, helping thousands of others in the process.

One post on AppalachianTrail.com encapsulated the conflict. Objecting to the idealization of Adam’s life, it read: “Adam Tarlin was from Brookline, Massachusetts. He was a person whose actual existence seems to be forgotten, somehow willfully overshadowed by a mythologized legend. I guess it’s easier to see him as some kind of folk hero, because it enabled people to ignore the fact that Adam was in incredible pain and far too lonely than anyone should ever be...to those of you who ‘knew’ Adam, I implore you to please think about the people you meet, whether hiking, or wherever you might meet someone, and think about why they might be there. Please don’t mythologize the lifestyle of someone who is lost and in pain. Please don’t glorify a homeless vagrant who has nowhere to go. Please let someone you know who has an alcohol or drug addiction know that you acknowledge their problem and their pain. Let them know that you are there to help them if they are willing to seek help. Help them get therapy, detox, rehab, find an AA meeting, whatever they are willing to do. Don’t ply them with alcohol for the purpose of YOU having a good time with them when they are totally lost to the world.”

The poster was Sharon Miller.

Many of the responses to the post were hostile, but Whitcomb reached out to Miller, and Miller said she was relieved to know that there were people who saw the real Adam, loved him, and would have done anything to help him survive.

At the Williamstown gathering, the two worlds came together. Erika was there. So was Adam’s daughter, Jillian, who is now 35 years old. According to some who attended, after many stories were shared, the service ended with an ovation. “It was such a tribute,” recalls Peoples. “All of a sudden, his real family knew. He wasn’t a black sheep. He was Baltimore Jack.”

As I mourned my friend and researched this story, I kept finding myself crying for somebody I hadn’t seen for decades, somebody I’d fought with during our time as classmates. It was, as everybody says, about Adam’s good heart. You could feel it. You pulled for Adam. That Adam’s truer, kinder self came out in Baltimore Jack is beyond question. The issue is whether it was ultimately, for a man who died young, a good thing. We all dream of living on the trail, out in the wild, with no responsibilities. Adam Tarlin showed that that was possible. Baltimore Jack showed that the reality isn’t as magical as it might seem. Those of us who’ve struggled, or seen a loved one struggle, with mental illness or substance abuse might see it another way. Over his life, Adam Tarlin lost his past—his parents—and his future, his daughter. One wasn’t his fault, one probably was.

We all dream of living on the trail, out in the wild, with no responsibilities. Adam Tarlin showed that that was possible. Baltimore Jack showed that the reality isn’t as magical as it might seem.

As I worked on this story, I realized that one of the reasons Adam’s choices felt so personal to me wasn’t just because I’d known him in college, but because I’d experienced a version of the narrative myself: my own father left when I was seven years old, deciding to travel the world in search of rare birds. I remember wondering, as I grew up, where he was and why he wasn’t with us. It’s something many of us rooted in the outdoor world encounter: a parent who seems lost to their own passions. I reconciled with my father when I was in my thirties, writing a book about the experience, but such reconciliations are never perfect. I had to understand that no matter how badly I wanted him to, he’d never be the father I wished he had been. I had to love and forgive him as he was.

In the days after his death, Adam’s daughter posted twice on his Facebook page. The first post expressed anger and grief over the father who’d left—both his family and this life—too soon. The second was forgiving. When I started working on this story, Jillian, who is married and works as a medical-surgical nurse in Boston, was hesitant to talk. But I reached out again, and we had a moving conversation. She refused to see herself as somehow wronged by the life her father had led.

She told me that Adam had made attempts to contact her over the years. “He’d send me a box of books every Christmas and birthday,” she said. “They were mostly books I wasn’t interested in—lots of medieval history.”

But she appreciated the effort. These gifts, she continued, indicated that Adam was trying. She had a memory of riding the swan boats with him in the Boston Public Garden, of him visiting her in Burlington, Vermont, and—as Jack always did when he had an audience—holding court with her friends and telling stories of life on the trail. She had visited him and spent a few nights on Vincellete’s property while she was in her early twenties.

She wanted to be closer. “I had this expectation that he needed to work harder, that he needed to invest more in terms of time and travel to forge this connection,” she says.

But in the end, Jillian says she realized she had to let that expectation go. “The truth is that I love my dad, and I don’t have any need to take him to task for anything. He did the things he needed to do. And I know he loved me.”