About Captain Tony’s – The Early Days
The building housing Captain Tony’s Saloon has a history as colorful as the town of Key West itself. When first constructed in 1851, 428 Greene Street was an ice house that doubled as the city morgue. In the 1890s, it housed a wireless telegraph station. The telegraph’s most important utilization came in 1898, during the Spanish-American War. The battleship Maine was destroyed, as the news came from Havana to Key West and it was reported all over the world from this building. In 1912, the building was home to a cigar factory and later a bordello. A few years later, 428 Greene Street‘s landlord leased the building to an individual named Morgan Bird, who opened the saloon as the Duval Club. He decorated the saloon in late-Victorian style. He threw large, lavish “gay” parties in the Duval Club, where the gay patrons propositioned sailors. Despite warning from the Navy, Morgan proceeded with his parties, until the Navy placed the Duval Club “off limits”. The Navy board’s action caused an 80% decrease in business, so Morgan was forced to close.
After that, it became several speakeasies, the last of which was named The Blind Pig, specializing in gambling, women, and bootleg rum.
In 1933, a local named Joe ‘Josie’ Russell bought the business and created Sloppy Joe’s Bar. The name came from Russell’s friend and fishing buddy, 
Ernest Hemingway and was suggested as a tribute to Hemingway’s friend in Havana, Jose Garcia, who owned a bar frequented by Hemingway and Russell, called interestingly enough, ‘Sloppy Joes.’
Originally, there was a long wooden bar was on the left side of the main bar area, the booths went to the back of the building and there was a large room off to one side used for gambling. The room had ceiling fans and sawdust floors and the only means of light came from two large French doors. Gambling consisted of roulette, craps, blackjack, one-armed bandits, faro and celo. Rumba was the music of the time and one could dance all evening to live music. The back room at Sloppy Joe’s (now the pool room at Captain Tony’s) was known as the Silver Slipper and served as the dance hall.
428 Greene Street was where Ernest Hemingway spent most of his evenings between 1933 and 1937. In 1938, when the building’s landlord raised the rent one dollar per week, Russell and his customers picked up the entire bar and moved everything in the middle of the night to Sloppy Joe’s current location at 201 Duval Street. Russell continued operation there until his passing in 1941. As a footnote, Hemingway loved the urinal at Sloppy Joes, which was actually a trough. During the move, it was taken to Hemingway’s house on Whitehead Street, where it serves as a cat trough in the garden.
The bar at 428 Greene then went through several iterations until 1958, when Captain Tony Tarracino, a local charter boat captain, purchased the bar and renamed it Captain Tony’s Saloon. As Captain Tony’s, the bar is where Jimmy Buffett got his start in Key West. Buffett played at Captain Tony’s in the early ’70s, and was often paid in tequila. Buffett immortalized the bar and Tarracino himself, in his song Last Mango in Paris”.
Captain Tony’s Today
Captain Tony’s Saloon has changed little since the days of Captain Tony at the bar and Jimmy Buffett on stage. It truly is a last piece of old Key West. The ceiling is covered with ladies’ bras, business cards fill the posts around the bar and every bar stool is painted with the name of a famous person who not only sat on it but also frequented the bar. The famous ‘hanging tree’ is still growing right in the middle of the bar and Tony’s jewfish still hangs above the door. Pool tables have replaced the slot machines and craps tables and rock and roll has replaced the rumba but overall it’s still the same friendly dive bar with great staff and cold beer. There’s live entertainment every afternoon and a live band every night and always a great crowd of locals and tourists alike.
Captain Tony’s is a Key West institution and a “must visit” for many returning Key West visitors. As one described it, “A seat at the bar and a couple of Pirate Punches – a great way to pass a hot Key West afternoon.”