The Colorful Legend of Captain Tony’s Saloon

By, Melissa Bryant

IMAGE11If you’re a Floridian, chances are you’ve visited Key West — a charismatic city known for its history, peculiarities and the unique, offbeat people it draws. Among them is Captain Anthony Tarracino, purveyor of a rustic dive bar called Captain Tony’s Saloon. Captain Tony’s spicy past inspired music, novels and film, and an impressive following of celebrity patrons including Ernest Hemingway, Truman Capote, John F. Kennedy, Jimmy Buffett and Shel Silverstein. Still, what truly gives Captain Tony’s an undeniably Key West flavor is its building on 428 Greene Street, which has operated as an ice house, morgue, telegraph station and a gay bar in centuries past. The story reads like an intriguing movie script. Let’s take a ride back in time.

Building at 428 Greene St.

Built in 1851, the building on 428 Greene Street was initially an ice house. The wide building’s doors made it easy for horses and their ice shipments to fit through since electric refrigeration had not yet been invented. Next, came its conversion into a morgue — a hanging-tree-at-capt-tonys-saloonnatural progression because of the need to keep bodies cold. Throughout the 1890s, the building on 428 Greene Street housed a wireless telegraph station. In 1899, during the Spanish-American War, the first word of the USS Maine being destroyed came through on wire at the building on 428 Greene Street. To this day, there is a hole in the top of the roof where the telegraph pole went through. The building became a cigar factory in 1912, and then several speakeasies, the last of which was called The Blind Pig — which specialized in gambling, women and Hoover Gold (the locals’ nickname for bootleg rum). Joe Russell opened Sloppy Joe’s at 428 Greene Street in 1933. It is this Sloppy Joe’s where Ernest Hemingway went to drink while he lived in the Keys from 1928-1938. After a rent dispute in 1938, the owner of Sloppy Joe’s moved the bar half a block down. Morgan Bird, the new owner of the building on 428 Greene Street, operated a gay bar in the 1940s and 50s called the Silver Slipper. In the early hours, Bird had Happy Hours that drew in military men. After the Navy placed the Duval Club “off limits” because of its clientele, sales declined and Bird sold the building.

Obit-TarracinoThe Legend of Captain Tony

Anthony Tarracino became the next proprietor at 428 Greene Street. But to properly set the scene, there are some important issues of his past worth noting. Captain Tony was born Anthony Tarracino on August 10, 1916, in 
Elizabeth, New Jersey. A rabble-rouser by birth, Tarracino left school in the ninth grade to 
manufacture and sell whiskey. Soon after, he gambled his way into hot water with the New Jersey mob, using his father’s television to beat the bookies. The mob pummelled Tarracino and abandoned his body at a Jersey dump. He recovered and then escaped on a Greyhound bus headed south with $16 in his pocket.

Tarracino landed in Miami and noticed a poster that read: “Visit Key West.” He hitched a ride on a milk truck headed to Key West. In the wee morning, Tony jumped into the nightlife scene of downtown Duval Street, which boasted gambling, bars, ladies of the night and loud music. That was 1948. By 1961, Tarracino, now a boat captain, became known around Key West as Captain Tony. He worked as a gunrunner, bringing weapons to the rebels in Cuba during the Bay of Pigs Invasion, all before buying the building on 428 Greene Street in 1958.

He renamed the establishment Captain Tony’s Saloon, which quickly became a favorite 
watering hole for locals. Tony was savvy enough to preserve the historical elements of the building. For example, patrons can see chains in the walls that were once used to tie up horses after they transported chunks of ice into the building when it served as an ice house. Captain Tony also kept a historic tree in his bar’s main pool room. Murderers, pirates and a woman accused of killing her family were all hung on Key West’s ‘Hanging Tree’. Locals say the woman who murdered her family haunts the saloon wearing the same blue dress she was hung in.

Remembering Captain Tony

Although Captain Tony passed away in November of 2008, his legend lives on through the history and traditions of his saloon. Every year on August 10th, Captain Tony is honored with a birthday party. Fans gather to hear personal retellings of his best stories and watch video interviews with Captain Tony. The present owner of Captain Tony’s, Joe Faber, says, “When you walk into the saloon, it’s filled with memorabilia about Captain Tony and his life.” And therein lays the key to Captain Tony’s 55-year success. “If you go into that bar today, it’s like going back to the bar 55 years ago. The history is still there and it looks exactly the same. You come and drink where legends drank. The names of the people on the barstools are not the names of people who had a drink and left — it’s names of people who came to the saloon over time and kept drinking there,” said Joe. And so, the legend lives on.

The Colorful Legend of Captain Tony’s Saloon