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  • Writer's pictureJenna Broughton

Drinking with Jack Kerouac at the Flamingo Bar

Updated: Apr 29, 2021

You can tell a lot about a person by where they like to spend their time. It is why I have made a practice of finding the former haunts of writers I am taken with. Because if I can see where a life was lived, especially the mundane parts, then I might get closer to the essence of a person who only exists in traces left behind on pages.

It is why I went to the Flamingo Bar in St. Petersburg, Fla. To see if I could get closer to Jack Kerouac.

It might sound odd to search for someone who has long since passed, but the place where I most feel a soul connection is in the reader and author relationship. It is the moments when I am able to express myself in a fully realized way through my writing or when another writer imprints words onto my heart.

With Jack it was his intellectual curiosity. The way his questions about life took him zig-zagging across the country from New York City to San Francisco. A lifestyle that was untethered and that only had a responsibility to the experience. His restlessness was palpable and his spontaneous prose, made famous in On the Road, buzzed with energy and had a musicality to it that I believe the best writing possesses.

Critics say Jack was solipsistic, but I was moved by the way he captured the madness of what it meant to be young and how the never-ending search for what all this life is supposed to mean can leave us heartsick and wondering. He didn’t gloss over the ugly parts and showed what sensitivity looked like alongside depravity. But mostly, I could tell that Jack felt too much, and I could identify with what it feels like to go through the world with all your nerve endings exposed. And somehow that made me feel seen and less alone.

So, I went to Flamingo Bar to see what I could understand about the man in the final years of his life.

By the time Jack arrived in St. Petersburg in 1964, his wandering ways had ceased, and he was weary from the weight of carrying the mantle of the Beat Generation. The rough edges of his life that had cut through the pages had begun to show their marks on him. The handsome face with eyes that twinkled had become bloated and ruddy, and his body was breaking down from health issues that often come at the hands of the bottle.

Even though Jack’s star had dimmed in the final years of his life, there was said to be a steady stream of fans who would show up at his St. Petersburg home at 5169 10th Ave. N. For someone desperate to escape the spotlight and himself, the Flamingo Bar’s shadowy ambiance was an ideal place to disappear into.

The Flamingo Bar is believed to be one of the last places Jack visited before he succumbed to cirrhosis of the liver brought on by alcoholism in 1969 at the age of 47. Sitting at the bar 50 years later, and I feel a twinge of sadness go over me for a man whose woundedness had been an asset on the page but became a liability in life and one that he could never get out from under.

In the last five decades the Flamingo Bar hasn’t changed much, and there is some solace offered by a place that is unaffected by time. The cast of regulars are welcoming and are unfazed by the reason for my visit, and I am offered a composition notebook they have for fans who visit. I scribble a note to Jack that I know wouldn’t mean much to anyone else.

The whole experience feels too brief, but I leave feeling like I have a better understanding of the man I had followed to this bar.

We are never the best nor the worst of what we put out there. But I had seen the best of Jack through his writing, and now I had seen his bottom at the Flamingo Bar. Maybe by knowing both, I got a better picture of the man.

Visit the Flamingo Bar at 1230 9th St N., St. Petersburg, FL 33705.

To support the efforts to restore and preserve Jack’s final home in St. Petersburg, donate to Friends of the Jack Kerouac House, Inc.


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