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Jack Kerouac found the end of his road in St. Petersburg 50 years ago

The King of the Beats is still celebrated throughout the city, including at his old drinking haunt, the Flamingo Bar.
Jack Kerouac was nearly unrecognizable in the late '60s (right) from the man he was in his youth (left).
Jack Kerouac was nearly unrecognizable in the late '60s (right) from the man he was in his youth (left). [ Times Files ]
Published Oct. 22, 2019|Updated Oct. 22, 2019

Jack Kerouac found the end of his storied road in a St. Petersburg hospital 50 years ago Monday.

The so-called King of the Beats is still celebrated throughout the city. For much of October, the Spirit of Kerouac Festival has events popping up around town. And Dale Nichols, owner of the Flamingo Bar — one of Kerouac’s only remaining haunts — still gets visitors looking to connect to a counterculture hero.

But the Jack Kerouac who lived in an unassuming house on 10th Avenue N with his mother and third wife, Stella, was not the folk hero of On the Road. He was not Dean Moriarty. He was not Sal Paradise. He was just Jack.

Jack Kerouac  [1977 Times file]
Jack Kerouac [1977 Times file] [ Times ]

“They kept mixing Jack up with Dean Moriarty,” John Clellon Holmes, one of Kerouac’s friends and a fellow member of the Beat Generation, said in the documentary What Happened to Kerouac? “They kept thinking Jack Kerouac was Dean Moriarty. In other words, Neal Cassady, which he wasn’t.”

The Beats came to prominence in the mid- to late 1950s. Kerouac’s breakthrough novel, On the Road, was published in 1957, close to a decade after it was written and more than 10 years after the events it chronicled. Almost overnight, Kerouac went from a struggling, nearly failed writer to the harbinger of the Beat Generation — an artistic movement of young writers who celebrated excessive vice, free sexuality and recreational drug use and rejected conventional society in the 1950s.

On the Road wasn’t the first work of the Beats or even of Kerouac’s, but its true-to-life tale of the fictionalized exploits of Kerouac and his friend Neal Cassady (written as Sal Paradise and Dean Moriarty, respectively) as they hitched, drove and partied their way across the country became a symbol for a frustrated youth. Its rambling, poetic, stream-of-consciousness prose inspired generations and remains widely sold and published.

In the time between living and writing On the Road, Kerouac had written, at least in part, more than a dozen novels. Once he became an avatar of the Beat Generation, his backlog hit the presses, too, many of his works being completed and published by the early ’60s.

And then, mostly silence.

Kerouac retreated from the limelight to the place he loved the most, the shadows. He picked up a bottle and never put it down.

According to Kerouac biographer Ann Charters, Kerouac once said, “I’m a Catholic and I can’t commit suicide and I wouldn’t do it to my family. But I plan to drink myself to death."

In St. Petersburg, he did just that.

The end of the road

A sign inside the Flamingo Bar, where Jack Kerouac hung out during his time in St Petersburg, advertises a special in the writer's honor.
A sign inside the Flamingo Bar, where Jack Kerouac hung out during his time in St Petersburg, advertises a special in the writer's honor. [ JAY CONNER | Tampa Bay Times ]
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Stepping into the Flamingo Bar is like stepping into a pocket of the universe that exists outside the normal constraints of space and time. It’s mostly unchanged since Nichols bought it in 1969. In there, it could be any decade.

With the haze of smoke and the sound of billiard balls being racked and cracked, dim light poking through narrow windows, it’s the kind of place that seems like it’s always night, always time for a drink.

It was just outside on one of St. Pete’s old green benches that Nichols would find Kerouac waiting at 8 a.m. for him to open the bar. He’d sit in the same corner stool and occasionally play a game of pool. He’d drink beers, a pint for a quarter, and pour in a nip of whiskey from his flask. He’d posture, talk big and rail about the Vietnam war. But the one thing he didn’t talk much about was writing.

“He never said, ‘I’m Jack Kerouac,’ when he was in here,” Nichols recalled. “He just introduced himself as Jack.”

Nichols met Kerouac in 1967. He was 24 and just back from Vietnam. One of his friends told him there was a guy he just had to meet, so one day they all gathered at the Sportsman, a pool hall at Second Avenue N and Second Street. Soon, Kerouac was running around St. Petersburg and Tampa with Nichols and his friends. They’d drink at bars that have since shuttered (save for the Flamingo), and occasionally Kerouac would get arrested for being too drunk. It happened at least once at the Wild Boar in Tampa, newspaper records show, and a few times in St. Petersburg, according to the city’s records.

The late author Jack Kerouac spent the last years of his life in this home at 5169 10th Ave. N.
The late author Jack Kerouac spent the last years of his life in this home at 5169 10th Ave. N.

Kerouac first came to St. Pete in 1964. Records show that’s when his ailing mother bought a house here. He bounced around for a few years until he bought his own house, the one next to hers, in 1968.

The Kerouac seen on T-shirts and posters, even the ones that still hang in the Flamingo’s window, show a young, strong, handsome man. It could be a poster from an old movie. But that’s not the man who lived in St. Petersburg.

The Kerouac here was a man in his mid-40s who, journalist Richard Hill said, looked more like he was 60. His bloated, blotched and blushed face had a permanent squint and scowl. His once athletic body was overweight and ailing. Doctors told him his liver was failing, and a hernia distended his gut.

The Jack Kerouac mural outside the Flamingo bar at 1230 Dr. Martin Luther King Jr. St. N in St. Petersburg.
The Jack Kerouac mural outside the Flamingo bar at 1230 Dr. Martin Luther King Jr. St. N in St. Petersburg. [ Courtesy of the Flamingo ]

The ’60s were a largely quiet time for Kerouac, but he was not wholly unproductive. In 1965, he wrote a series of sports stories for the Evening Independent, a defunct daily paper that was owned, at the time, by the then-St. Petersburg Times. The stories appeared in both papers with ruminations on boxing, baseball and sports writing itself.

“Jack Kerouac did more than just die here,” Kristy Andersen, a St. Pete resident working on a Kerouac documentary, said. “He had huge problems with celebrity. He didn’t like being recognized. I think he felt he could lose himself in Florida.”

John Sampas (left) and Jack Kerouac in Lowell, Mass., in 1966.
John Sampas (left) and Jack Kerouac in Lowell, Mass., in 1966. [ HANDOUT | Courtesy of John Sampras ]

In St. Pete, Kerouac hung out with young men returning home from war looking for adventure, much like he had 20 years prior. He finished his last novel, an often overlooked work called Pic, while here. It was published posthumously after his death and is out of print.

For research, Kerouac spent time in traditionally African-American sections of the city. He went to baseball games at segregated stadiums and sat in the black section. He was searching for a voice. Some of that voice is evident in Pic, which chronicles the travels of a young black child from a broken home who traverses the country with his brother. It’s a departure from his mostly autobiographical fiction, but its essence was Kerouac — a fatherless boy on the road searching for meaning.

Young Jack Kerouac.
Young Jack Kerouac. [ Times (undated) ]

Kerouac’s St. Petersburg exploration took him to the Cactus Bar on the city’s south side, a historically African-American neighborhood. According to Kerouac’s friends and biographer Paul Maher, the story goes that after a verbal altercation in the bar, Kerouac was beaten, suffering broken ribs among other injuries.

Kerouac mentions getting into a fight at a bar in St. Pete in a September 1969 letter to his ex-wife, Edie Parker, however the St. Petersburg Police Department said it does not have record of a fight at the Cactus Bar around that time. Police officials did, however, say that not all records from that far back have been preserved.

In Kerouac: A Definitive Biography, Maher wrote the “vicious beating at the Cactus Bar had been the final blow.”

On Oct. 20, 1969, Kerouac began vomiting blood. He was taken to St. Anthony’s Hospital, where doctors spent hours trying to tie off the busted abdominal vessels that drained his life.

“The poor guy was in shock from the time he hit the emergency room,” a doctor told the Times in 1969, “and we never really got him out of shock.”

Doctors pumped 30 units of type A blood through Kerouac. After his surgery, the hospital had a shortage.

He died at 5:45 a.m. Oct. 21. He was 47.

He gave the world the Beats, which became the hippies; he mostly hated both. He was, by all accounts, a walking contradiction. He was tender and pensive, but brash and quarrelsome. An angry drunk and a disembodied poet.

"I made myself famous by writing songs and lyrics about the beauty of the things that I did and the ugliness, too,” Kerouac said on a 1968 episode of William F. Buckley’s Firing Line. “It was pure in my heart.”

The Flamingo Bar will hold a celebration of Kerouac’s life on Oct. 26. The bar still celebrates one of its most legendary customers twice a year, honoring the day he entered the world and the day he left it.


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