Tony Tarracino

Childhood

Born on August 10, 1916, in Elizabeth, New Jersey, Tony Tarracino was the son of an Italian immigrant bootlegger. His early years were marked by hardship—he dropped out of school in the ninth grade to sell whiskey during Prohibition, an illegal but lucrative trade that introduced him to the underworld.

By his twenties, Tarracino had become a gambler, betting on everything from horse races to boxing matches. His involvement with the New Jersey Mafia nearly cost him his life when he was beaten and left for dead at the Newark city dump after allegedly cheating the mob by using early race results obtained via telephone—a scheme he later likened to the plot of The Sting.

Career

Early Years in Key West

After fleeing New Jersey, Tarracino arrived in Key West in 1948, where he reinvented himself as a shrimper, charter boat captain, and gunrunner—smuggling weapons to Cuban rebels during the Bay of Pigs era.

Captain Tony’s Saloon

In 1961, he took over the historic 428 Greene Street bar, originally Sloppy Joe’s (Ernest Hemingway’s favorite haunt). Renaming it Captain Tony’s Saloon, he turned it into a legendary Key West institution, frequented by celebrities, writers, and fellow gamblers.

Political Career

Despite—or perhaps because of—his rough-edged persona, Tarracino ran for mayor of Key West four times before winning in 1989 by just 32 votes. His campaign, managed by Jimmy Buffett, promised to preserve Key West’s eccentric charm. He served until 1991, famously protecting the daily sunset celebration and resisting overdevelopment 23.

Personal life

Tarracino was married four times, lastly to Marty Tarracino for 38 years until his death. He fathered 13 children with multiple partners, including reality TV star Keith Famie (Survivor: The Australian Outback). His youngest son, Tony Tarracino Jr., was born when he was 70 years old.

Revenue

While exact financial figures are scarce, Tarracino’s income streams included:

• Captain Tony’s Saloon (1961–1989, later sold but remained a fixture)
• Charter boat fishing and gunrunning (1950s–60s)
• Political career (mayoral salary, though likely modest)
• Book sales (Life Lessons of a Legend, co-authored with Brad Manard)

Interesting facts

• Cheated the Mob: Used early race results to outsmart bookies.
• Gunrunner for the U.S.: Supplied weapons during the Bay of Pigs.
• Immortalized in Song: Jimmy Buffett’s "Last Mango in Paris" was inspired by him.
• Movie Star: Played by Stuart Whitman in Cuba Crossing (1980).
• Oldest Mayor to Father a Child: Had a son at age 70.
  

Legacy

Tarracino’s legacy lives on through:

• Captain Tony’s Saloon, still a Key West landmark.
• His autobiography (Life Lessons of a Legend).
• Key West’s "Captain Tony Day" (August 10, his birthday).
• His influence on Jimmy Buffett’s music and Key West’s cultural identityю