In 1967 Key West's favorite local character, Capt. Tony Tarracino, 69, campaigned barefoot for the office of mayor and lost by only 86 votes. In 1972 he wore shoes, shaved and lost again. Last year he got singer Jimmy Buffett to manage his third campaign, only to lose by 52 votes to a man with even greater name recognition than his own—Tom Sawyer. Undaunted, Tony is now considering running for Governor of Florida. If he does, the saloonkeeper and sea captain will be the first confessed former gunrunner, gambler, adulterer and "small-time hustler" ever to seek that office.

Tony's third wife, Marty, 37, recently bore him his 13th child, Tony Jr. Captain Tony's kids have five different mothers. He's now writing his memoirs and planning to franchise his legendary saloon. Each clone will be called "Captain Tony's, Originally of Key West" and will be filled with the sort of flotsam from Key West's conch culture—chastity belts, toilet seat covers, lewd photos—that decorates the original, Tony says. Busy as he is, the short and salty, raspy-voiced chain-smoker still spends his evenings holding forth at his bar. Belly up and listen:

When I ran for mayor last year, it was because two old ladies came up to me in a grocery store and begged me to. They couldn't afford more than a 25-watt bulb in their reading lamps, and they said, "We need you, Tony." They had tears in their eyes.

I wanted to help them. I'm a peasant at heart. And a hustler. I talk the way people think. They're afraid to say it, so I tell it like it is.

I was born in Elizabeth, N.J. My father was a bootlegger. My mother's family were puppeteers. Me and my three brothers, Sal, Louie and Joey, grew up in an Italian ghetto. Each neighborhood was a separate country. If I went out of my country into another, I'd get the hell knocked out of me. I was too small to fight, so I learned to talk and hustle. But my childhood was rich in love.

I was in love with my eighth-grade teacher. She told me I should drop out of school because there was nothing for me there. "You belong to the world," she said. "Go see it." She set the stage for the rest of my life. Whenever I think of her, it's like smoking a joint. She was a mother walrus. All my women are like her in some way.

In the years after I left school, I gambled a lot to support myself. I already had a wife and kids, and I had a lot of odd jobs—newspapers, tool and die, union organizing—but gambling always won out. It was the only thing that raised my standard of living. If I had a choice between heaven and Vegas, I'd drop the wings and go to Vegas.

In 1948, after a horse-betting scam in Jersey, I got the shit beat out of me by a couple of the boys. I pulled myself out of a city dump at Newark airport and drove to Miami in a pink Cadillac with a blond bombshell.

My wife had divorced me by then—you couldn't blame her. I had a kid by a beautiful Puerto Rican girl, lived with an Eskimo and made love to a hell of a lot more. I don't remember their names, but they was all beautiful people.

We landed at Hialeah Park racetrack, the blonde and me. I had found paradise like a Jew discovering Israel. We stayed a month. When I was down to $118, I gave the blonde $100 and the car and told her to go home. I took the last $18, rode the bus to Homestead, then hopped a milk truck to Key West.

When I arrived, my eyes popped out of my head. It was incredible, like the Barbary Coast—wide open strip joints, gin mills, hookers everywhere. Beds above the bars, crap tables, slots. I thought, "This town is for me."

It was 4 a.m. and, believe it or not, the first place I went was the Duval Club, now my Captain Tony's Saloon. I downed the last 15-cent beer of the evening, then passed out in a 1932 Plymouth that smelled like urine.

When I woke up the next day, an old woman gave me a job heading shrimp for a quarter a bucket. I knew right away Key West was home. I loved the coconut trees, the flowers, the sea, the red snapper. I fell in love with the people. I saw the islands as a place where all walks of life could live together. Nobody cared if you were a hooker, a bum, gay or straight. The only outcasts were the snobby rich.

I worked on the shrimp boats for $100 a week till my hands swelled so bad I couldn't use them. Then I bought a 36-foot charter boat called the Greyhound and got my captain's license. For $5 a head, I took people out to sea. I was so proud to hear people call me Captain Tony. Here I was, a small-time hustler, and nice people respected me.

In the late '50s I got involved with some mercenaries who wanted to invade Haiti and kill Papa Doc. It never happened, because one of them died in an accident with live ammunition. We were put on trial in Miami. I got off, and you'd think I'd have learned my lesson. But no. I'm always taking chances. In the late '50s, when the U.S. was still helping Castro, a guy paid me $10,000 a trip to haul guns, ammunition and radios over to Cuba by boat—a seven-hour trip. I made 10 or 12 trips over. There's a film about it called Cuba Crossing.

After Castro won and told those against him to take their people out, I was paid $15,000 to sneak into Cuba and bring them to Miami. I made headlines, and the Cubans kissed my hands when we arrived in the U.S. I felt so good, I didn't care about getting arrested. I spent only one night in jail because someone in Washington saw to my release.

When I bought my bar, it was popular with gays, not military men, and I was romancing the wife of a naval officer. I met Morgan Bird, the gay owner who was losing his ass because he had been put off-limits by the military and was going out of business. So I picked up the bar for $35,000 in 1963 and named it Captain Tony's Saloon.

In the 1930s it was called Sloppy Joe's, Ernest Hemingway's favorite place. He met his third wife, Martha Gellhorn, here. When the rent was raised $6 a month, the owner moved the bar to an abandoned skating rink across the street and kept the name. They still claim Hemingway did a lot of boozing there. But he lived in Cuba after 1938 and only occasionally drank at the new Sloppy Joe's. He would roll over in his coffin if he ever heard them promoting "Hemingway's Piña Coladas." He was a scotch man like me.

Every afternoon Hemingway was in Key West the barkeep had to save four barstools for him and his fishing buddies. He had a corner gang, almost a clique. He was a great writer but a shit of a human being. A loner. Not friendly. Always thinking. He wrote To Have and Have Not in this bar.

You can't believe the intelligent people who drink in this bar. They develop a reverence for the place. All the news stars—I love those guys—Dan Rather and especially Walter Cronkite. I put his name on a barstool. He's a great captain.

Jimmy Buffett got started on my stage. He wrote Margaritaville about Key West, and his album Last Mango in Paris was about me. When Truman Capote came in, if he was out to score, he'd drink crème de menthe. He liked plump, pink-cheeked kids from Idaho. He also liked to follow the military men into the bathroom and watch them. I was always protecting him, afraid that with the way he called them guys "dahling," he'd get killed by a sailor without a sense of humor.

Truman had a fling with Tennessee Williams. They would dance together in here like two grandmothers. How I loved Tennessee. My brother Sal introduced Tennessee to Frankie Merlo, who later became Tennessee's lover. I met Tennessee through Frankie about the time The Glass Menagerie opened in New York. Tennessee was beautiful, compassionate and understanding. You could see it in his eyes. He asked me to care for his two monkeys, Creature and Lioness, while he traveled. When Lioness died, he held him in his arms and cried. And poor Creature. He lived in a cage here in the bar before some whacked-out people fed him pot, rum and Quaaludes. I took him home and built a cage in the yard. When he died, Tennessee called from New York and asked if Creature had suffered. Soon after, he came home and placed a cross where Creature was buried. That night he was so messed up he came into Captain Tony's dressed only in a bathrobe. He was dancing wildly and flashing all the guys. A few weeks later I got a call from my brother in New York that Tennessee had died. I was so upset. He was part of my family.

So many people I've met in the bar are like family. They're the ones who keep encouraging me to run for public office. First it was the hippies who convinced me to run for mayor. Now people all over the country want me to run for Governor of Florida. Clint Eastwood says go for it. I'll have one hell of a campaign. If elected, I might wear a suit and tie. And I might not. But I would take a shower every day.

  • Contributors:
  • Linda Marx.