The odometer broke, thousands of miles and a lifetime removed from the all-night neon hustle of Times Square and the evergreen Zen of the northern Cascades, the pagan thunderclap poetry of the Big Sur coastline and the redbrick sadness of smokestack Lowell. In his final sighs, Jack Kerouac found himself unmoored from the moonlit amphetamine rambling of his own fables. No more thumbs out hitchhiking in ’49 Hudsons, past apple pie diners and the lonesome shadows of grain farms in the flat Midwestern infinity. To riff on a phrase from an Aquarian band inspired by the Beat Generation avatar: This was the end. 

In the last year of the sixties, the On The Road author had become a bloated phantom, chasing Johnny Walker with half-quart cans of Falstaff beer while secluded in St. Petersburg, Florida — a slow-motion suicide in a spring-training town, about as far away from Route 66 as you can get. He called this place the home of “the newlywed and living dead.” And for a little while, Kerouac was both. 

The inconvenient parts of the myth get left out of the Levi’s commercials. No one wants to remember the brokedown jester decomposing on the Gulf Coast — trading drunken slanders with his paralyzed mother, watching black and white television with the sound off — when you can deify the blue-eyed, slim-waisted Odysseus. Kerouac’s bones splinter beneath an unremarkable grave in Lowell, the rundown Massachusetts mill town where he was raised. But his last residence in St. Petersburg is the real tomb, a cinderblock cenotaph practically untouched since his funeral, nearly two months after Woodstock, a final shovel of dirt atop the casket of the hippie decade that he manifested but disavowed.

“This place is like Disneyland for psychics,” says Ken Burchenal, the owner of The Jack Kerouac House of St. Petersburg, shortly after I step through the door of the 1,800-square-foot ranch home.

It’s a weekday in the gut of autumn, almost the exact anniversary of the day, October 21, 1969, that paramedics rushed Kerouac to the hospital after he started vomiting blood in this mint-tiled bathroom. The doctors at St. Anthony’s Hospital couldn’t stanch the hemorrhaging. His body rejected the transfusions. After fifteen excruciating hours, his pulse finally surrendered. He was 47 years old. 

Kerouac’s last home is so immaculately preserved that you expect to hear a vintage Underwood being throttled at high speed in a back room. In fact, Burchenal ensured that his one-time writing chamber still has a blank sheet of white paper slipped through a 1957 Royal, taunting you to compose your own spontaneous bop-prose requiem. 

“He died with only $91 to his name,” Burchenal tells me. “Most of his net worth was tied up in this house.” 

While Allen Ginsberg became the literary conscience of subterranean radicals, Kerouac was strapped for cash, complaining that college kids bought $10 hardback copies of Catcher in the Rye while “bums” bought one paperback of On the Road and shared it with ten people. None of his later books sold very well. The publishing industry considered him all “written out.” In the last profile ever published about him, Kerouac caterwauled about only making $1,770 in the first half of 1969 ($17,000 today, adjusted for inflation). 

In 1973, Gabrielle Kerouac died and left the estate to Stella Sampas, her son’s third wife. Seven years earlier, Jack had married Stella — the older sister of a childhood best friend killed in World War II — to ensure care for his mother, a stroke victim. For the last 27 years of her life, Sampas lived the life of a widowed Florida retiree, attracting a reputation as the nice old lady who baked chocolate chip cookies and overpaid neighborhood kids to mow the lawn. After Stella’s 1990 death, her youngest brother, John Sampas, was named official heir and literary executor. The former owner of the Indianapolis Colts purchased the original 120-foot scroll of On the Road for $2.4 million. Letters were auctioned off. Unpublished early manuscripts and poetry collections hit bookshelves. The front porch and backyard became a subtropical jungle, but the interior was embalmed in the Brady Bunch era. Sometimes, Kerouac pilgrims left candles on the porch and letters in the mailbox (until it was stolen).

In court, the Kerouac Estate waged decades of probate combat. Kerouac’s daughter from a previous marriage, Jan, whose paternity he never officially acknowledged, sued, claiming that her grandmother’s will was forged. After hearing testimony from a doctor and a handwriting specialist, a judge ruled in 2009 that Gabrielle Kerouac’s signature was faked. By then, Jan Kerouac was long dead. A surviving nephew, the destitute son of Kerouac’s sister, petitioned to carry on her suit in his name, but eventually the Sampas family secured control of the $20 million dollar estate. 

In 2018, John Sampas died, leaving everything to his adopted son, John Shen-Sampas. In the first days of the pandemic, Shen-Sampas finally resold the Kerouac house, which, even then, still contained closets full of Kerouac’s clothes and two filing cabinets of unfinished work. A nonprofit called the Friends of Jack Kerouac hoped to buy it, but Sampas sold it to a home-flipping company with a Carl Hiaasen name, “Flip Side LLC.” Before the escrow closed, Johnny Depp bought a pair of Kerouac’s jeans for $5,000.

The Flip Siders fixed the broken windows, the air conditioner, and the leaky roof. They gave the dilapidated exterior a coat of fresh white paint, trimmed the stubby palm tree on the front lawn, and exterminated the beatnik rodents that were squatting. In October of 2020, one week after 5169 10th Avenue North was put on the market, Burchenal, a retired University of Texas-Austin professor, snatched up the three-bedroom, three-bath residence for $360,000. 

“My wife and I had just sold our share of my parent’s citrus farm and had been looking for something to invest in,” Burchenal says. “Our daughter sent us a link to the house and it was love at first sight. We saw it Saturday, and bought it on Sunday.” The Burchenals soon established a nonprofit foundation for the house. Its status as a historic landmark ensures that it can’t be demolished or substantially altered. And so, it has become central Florida’s answer to Ernest Hemingway’s French Colonial mansion-turned-museum in Key West.

But only cats can stay at the Hemingway House after dark. For $250 a night, you can sleep on Kerouac’s literal deathbed, next to Book of Dreams lying on the end table. You can use the solace and space to sip whiskey, chainsmoke on the screened back porch, and heed his advice to “scribble in secret notebooks for yr own joy.”

I ask Burchenal about the circumstances of Kerouac’s death. Most biographers and his fellow Beats attributed it to an abdominal hemorrhage caused by cirrhosis. And no one disputes that alcoholism rotted Kerouac’s internal organs and immune system. But down here, another explanation took root. 

“About a month before he died, Kerouac went to the Cactus Bar, which was on the African-American side of St. Petersburg,” Burchenal says. “Somehow or another, Jack started speaking in the slang and voices of the characters from Pic. Understandably, the guys in there thought that he was mocking them, and took him out to the parking lot and beat him up so bad that he never recovered. That’s really what killed him.”

Burchenal explains that he personally heard the story from a friend of the retired Air Force lieutenant who had gone drinking with Kerouac on that fateful night. It isn’t the story found in Ann Charters’s 1973 biography, but later chroniclers, digging through hospital records and letters, came closer to the truth. The savage thrashing left Kerouac with broken ribs and black eyes. Afraid of hospitals, he medicated with whiskey.

“The Cactus isn’t here anymore. The only bar left that Kerouac hung out at is the Flamingo,” Burchenal adds. “The owner actually used to be a bartender there and knew Kerouac. They have two pool tables in there if you like to shoot pool — well, three, but you can only use the third one if the owner likes you.”

The next day, before I head to the airport, I take a detour to the Flamingo, a dingy, smoke-choked, cash-only dive owned by a Vietnam vet who remembers Kerouac showing up to drink at 8 AM with a newspaper tucked under his arm. It’s now populated by leathery, hard-living regulars with biker beards, leg tattoos, and Blue Lives Matter baseball hats. Scruffy beach bums twist up joints next to a Kerouac mural outside.

But at present, Burchenal runs through the logistics of the property. Kerouac’s house now has wireless internet, Roku, a Keurig machine, and a few commemorative bobblehead dolls. It’s been modernized, but hasn’t lost its taxidermied eeriness. 

“Feel free to putter around. There’s nothing sacred here — well, just one thing,” Burchenal says, pointing to a small figurine of the Madonna, propped next to a lamp. “Don’t touch the Virgin Mary.”

When I was 20, I started hearing voices in my head. Without warning, fragments of poems and plots of future novels beamed into my brain. It wasn’t the tin foil shriek of schizophrenia, but something closer to the divine transmissions of a 24-hour pirate radio station that played mostly Mos Def and Pharoahe Monch from midnight till 3 AM.

In the previous six months, my grandmother had died of ovarian cancer and one of my college baseball teammates was killed in a car accident on a frat hazing trip. For the first time, I experienced the irreparable power outage of death, and tangibly understood that it would eventually turn out the lights of me and everyone I loved. Soon after, I started experimenting with psychedelics and indulged the epiphany that I was no longer what I had been. 

Until I was 13, reading consumed my waking life. At the dimly lit taco spot where my family ate Sunday nights, the waitress only knew me as the “little boy with the book.” Only later did I recognize this as an instinctive distraction from the terrorizing rage that my father inflicted upon my mom, sister, and me. In eighth grade, I became obsessed with The Basketball Diaries, agreeing with the back-of-the-book assessment from someone named Jack Kerouac, who claimed that “at 13 years of age, Jim Carroll writes better prose than 89% of the novelists working today.” In emulation, I snuck away at recess to scribble my own alienated screeds. 

By freshman year, reading anything deeper than The Source signified that you were a total loser, so I publicly and privately renounced all signs of intelligence. I started on the varsity baseball and basketball teams, narrowly fixated on girls and rap, and frequently found myself in the vice-principal’s office for bad behavior. Apart from being named the sports editor of the high-school paper, there was little evidence that I’d ever write. Even then, I only lasted a month before the faculty advisor fired me for insubordination.

During my sophomore year of college, I spied slim orange volumes of Kerouac in the dorm room of my most literate drinking buddy, who mentioned that it might be worthwhile to investigate the Beats. And even though On the Road was already a half-century old, it instantly converted me to the doctrine that life required spontaneous treks through unfamiliar territory in search of bizarre characters and folkloric adventure. I wouldn’t necessarily recommend Kerouac to anyone old enough to rent a car, but his best work is a lightning bolt emitting the revolutionary energy of youth. If it strikes you at the right time, it can recalibrate the magnetic poles of your life. It’s not supposed to carry you to the final destination; it’s meant to hotwire the engine. 

Kerouac’s own narrative made it feel personally ordained. Ginsberg called his corpus “sacred athletic wisdom,” and I saw room for myself in literature via the scholarship running back who quit Columbia’s football team after feuding with the coach. Until that point, my entire life could have been explained by the opening of 1967’s Vanity of Duluoz: “My particular form of anguish came from being too sensitive to all the lunkheads I had to deal with just so I could get to be a high school football star.” The next year, I led a walkout of my college baseball team and never looked back. 

By then, I was scrawling obsessively in a City Lights journal gifted to me after a series of genuflections at the North Beach altar. Writing became a biological necessity and a bitter compulsion. Amidst a cosmic fungi orbit, apparitions of Ginsberg and Kerouac instructed me to “shepherd my gift.” Depending on how much stock you place in drug-induced visions, I saw my destiny mapped out in the stonewashed pattern of my blue jeans. 

Before I could misplace my diploma, my roommate and I hit the road for a month. We rambled through the ragged splendor of America, sleeping on steel mattresses in $30-a-night motels, meditating atop remote canyons, listening to wailing guitar wizards in neglected stations of the cross (Memphis). We ambled through arcane local history museums run by elderly volunteers and wolfed cigarettes inside rowdy dive bars with $3 Happy Hour specials. Maybe these gestures of faith were all overly predictable, but what skeptics consider cliché is another person’s way of honoring tradition. 

No matter how much I believed in the antique fantasy, I understood that what I was searching for — the idiosyncratic monuments and handmade craftsmanship, the regional mutations and countercultural pockets of resistance — was becoming increasingly endangered. The highways were crumbling. My father regularly indicted me for picking “the world’s worst profession,” but I was willing to sacrifice a nuclear family, regular working hours, and financial stability to follow a genuine calling. After answering a Craigslist ad for an entertainment reporter at a celebrity magazine, I fell into a sinkhole created by a rupture of the San Andreas. 

In four years of tabloid perdition, I covered Afghan charity relief galas and film premieres and cheated the reaper on 100 mph paparazzi chases through the Hollywood Hills. I stood outside of Avril Lavigne’s wedding, and was “arrested” for accidentally trespassing on Brad Pitt’s Santa Barbara fiefdom.

These warped memories are tumbling back to me, alone in St. Petersburg, rocking in this rickety wooden chair, house-sitting Kerouac’s revenant. All the lampless stumbles down this lefthand path, the decades of false starts, and the disquieting rejections. The civil war with my own limitations, where I learned that writing isn’t a calling, it’s an affliction. In his essay on “Belief & Technique For Modern Prose,” Kerouac urged novitiates to remember that “you’re a genius all the time.” But Philip Roth’s description of writing is far more humbling: “It’s daily frustration, not to mention humiliation. It’s just like baseball: You fail two-thirds of the time.”

The once-uninterrupted choral ensemble in my head stopped harmonizing a long time ago. But against my rational and fiscal instincts, I have refused to quit writing, which feels significant at a time when it often seems irrational and obsolete.

Be wary of anyone who tells you to follow your dreams. It’s a fairy tale that you hear from someone onstage, not the end of the bar. But for a few breaths on this plaintive Thursday night in Florida, I am briefly at peace, silenced by gratitude, free to reminiscence on the journey in this florid resting place of a formative inspiration. And there happens to be a bottle of leftover whiskey in one of the cabinets. 

It’s been said that you should kill your heroes, and Kerouac made it pretty easy. Little of his work seriously contends with the consequences of actually trying to live like a Roman candle. While most of his books contain passages of high-voltage genius, his mantra of “first thought, best thought” did few favors for the finished product. It’s no accident that his most remembered novel, On the Road, was the most heavily rewritten. And even then, one of the flashes of insight at the end is that… “God is Pooh Bear.” 

In 2017, I tracked down the surviving Beats — Lawrence Ferlinghetti, Diane di Prima, Michael McClure, and Gary Snyder — for a four-part series in the Washington Post. Snyder is the only one still alive, a 95-year old bodhisattva living off-grid in an isolated 100-acre compound atop the Sierra Nevadas. When we talked at Kitkitdizze, the inspiration for Japhy Ryder from Dharma Bums distilled his late friend’s contradictions with cold-water clarity. 

“Jack wasn’t a terribly good thinker, but he was a good writer, who certainly did have a way with language,” Snyder, who won the 1975 Pulitzer Prize for poetry, told me. “It’s a wonderful, naïve, Catholic-boy energy.”

Kerouac could be prejudiced against Black people and Jews. He wrote about women like a guy who lived with his mom until the day he died. His most indefensible act might have been the cruelty displayed towards his only child, a talented writer, whom he completely disavowed. He was a man of his time, and not a particularly honorable one. 

Kerouac shrewdly canonized other subjects — Neal Cassady, Snyder, his saintly older brother Gerard, who died at age 9 — while letting his own literary alter egos bask in refracted, edge-of-the-frame glory. Other than 1962’s Big Sur, a bleak vivisection of his own unraveling, Kerouac was more interested in self-mythology than nuanced, three-dimensional portrayals. And while no artist owes any fidelity to a perceived objective truth, spiritual honesty carries an unmistakable weight. 

If booze and speed hadn’t submerged Kerouac early, he may have reached a more complete final form; may have attempted to reconcile his sexual confusion, Oedipal dramas, and fecklessness in confronting the pain of existence. But the flaws only matter so much when you write with preternatural soulfulness and velocity and are photogenic enough to (posthumously) sell khakis in a Gap ad — which actually happened in ’93.

In Kerouac’s old suburban tract home, half-drunk on an Indian summer night, the question of posterity is never very far from my mind. It’s been fifty years since Gore Vidal — who famously bragged about his one-night stand with Kerouac — declared that the “future is dark for literature… The young in general are not going to take up reading when they have such easy alternatives as television, movies, rock.” In a hyperreal world of doomscrolling, where few read anything longer than an Instagram caption, it’s unthinkable that any literary work could today create a tectonic shift like On the Road did. There are two historic Kerouac houses in Florida alone — including the two-bedroom bungalow in Orlando where he wrote Dharma Bums. If you’re a novelist under 50 today, you’ll be lucky to get a few RIPs on Bluesky after your ride in a hearse. 

Rolling myself a cigarette on the porch, I eavesdrop on the nagging beep of the crickets, watching the lizards scurry across the wooden railing, and consider what Kerouac might have said about this recycled scrapheap world: where microdosing technofeudalist overlords are stripping all of society’s remaining catalytic converters and feeding all the cultural artifacts of the “before times” into a silicon matrix to distract us from our own suffering. What is the value of screaming into the void? How do you follow the road less traveled when the turn-off is obscured by oblivion.

Standing abruptly, woozy from the liquor and tobacco, I stomp into the living room, stopping at the chestnut-dark bookshelf filled with Kerouac classics, Beat ephemera, and religious iconography. Selecting Visions of Cody, I collapse onto the overstuffed tan sofa and flip through it. This was Kerouac’s personal favorite, a more experimental alternative version of On the Road, mostly written in the early ’50s, which went unpublished until after his death. While the stretches of the taped conversations between him and Cassady can swerve into solipsistic cranked-up delirium, there are gorgeous cataracts of stream-of-consciousness prosody where it sounds like he’s deciphering celestial directives.

Turning back to the beginning, I freeze on the dedication: “To America, whatever that is.” In his prologue, Kerouac explains that he wrote the book as an “enormous paean which would unite my vision of America with words spilled out in the modern spontaneous method.” Cassady is rendered as the archetypal American man, the manic rebel hero of the West Coast. This is partly what mesmerized me when I was young: the liberating possibilities of the big-sky horizon, the glittering triple-time rhythm of the dialect, the Romantic desire for unrestrained experience. 

When I reread it now, what strikes me about Kerouac is that his books are requiems for an already vanished world. This paralyzing loss is at the heart of his sadness. It’s there, in the same prologue, where he presciently mourns that these feelings may become “obsolete as America enters its High Civilization period and no one will get sentimental or poetic any more about trains and dew on fences at dawn in Missouri.” 

Last summer, I watched the skeletal vestiges of the Grateful Dead sell out Golden Gate Park, where the children of this century sang along to psychedelic blues catechisms about wanting to be a headlight on a northbound train. And while the numbers will eventually dwindle, adolescents will always discover Kerouac and go searching for revelations on the rolling continent — if they can afford the fuel. But with each passing year, the relics become harder to find or encased in expensive glass. Those attempting to sustain the heritage often fall victim to the curse of postmodernity: the awkward irony, the insecure insincerity, the sickening suspicion that you are watching a well-rehearsed spectacle.

After a few careening pages of Visions of Cody, a gross digression about masturbation derails me, and reminds me why praising Kerouac always involves a caveat or two. Putting the book down, I prowl around the house some more, pausing in his writing room. For a moment, I’m lured by the siren of the typewriter. Above it, there is a taped printout of a 1957 letter from Kerouac to his then-girlfriend, Joyce Johnson, which cites this exact Royal model and asks her to pick up a copy of his career-making On the Road review. At the time, the New York Times was hard to find in Florida.

The thought of playing dress-rehearsal Kerouac on a replica typewriter feels corny and repellant. So I take a notebook from my backpack that hasn’t been touched in too long, and let my thoughts drift in any direction for an hour or so. Nothing is particularly profound, but for the first time in months, I remember why I love writing. Somewhere along the line, my need to stay afloat had fused with my ambition, and I had forgotten that self-expression is the only thing that matters. And no matter what you can say about Kerouac, no one fought harder to remain free. 

In the sultry heat of his final summer, it was said that Kerouac used to drag a cot out here and doze off under this very same ancient blanket of light. I wonder right now if he knew that the end was near, if he felt that all the agony and exhaustion in the service of novels and poems was worth it. The blood and sweat brought him neither peace, nor enlightenment, nor financial stability. But it carried me here.