The Story of Josie Russell and Sloppy Joe's Bar Key West

Sloppy Joe's Duval and Greene Streets   Key West

     A long time in Key West there was a bar owned and operated by a man named Josie Russell.   Joe Russell was a charter boat captain, a rumrunner, Ernest Hemingway’s boat pilot, and fishing companion for some twelve years.  Prohibition was looked on as an amusing exercise dreamed up by the government and Josie Russell was just one of several individuals who operated illegal speakeasies. Key West residents including Papa Hemingway, would stop by his home occasionally  to buy illicit bottles of liquor.

 

Josie Russell and Papa

    The official beginning of Sloppy Joe’s Bar, the famous and infamous Key West saloon, was December 5, 1933–the day Prohibition was repealed. The bar would to go through two name changes and a sudden change of location before it would become Sloppy Joe’s,    When Prohibition ended, Josie Russell became a legitimate saloon-keeper-proprietor of the “Blind Pig”, a droll rundown building that Russell leased for three dollars a week.   The rowdy, come-as-you-are saloon was remodeled and renamed the Silver Slipper, with the addition of a dance floor.   It didn’t matter–it remained a the same  shabby uncomfortable place where good friends, gambling, fifteen-cent whiskey, and ten-cent shots of gin could be enjoyed.  It was Hemingway, a favorite patron of Russell’s bar from the start, who encouraged its name change to Sloppy Joe’s. The new name was adopted from Jose Garcia Rio Havana club of the same name.   Because the floor was always wet with melted ice, his patrons taunted this Spanish Joe with running a sloppy place… and the name stuck.

Sloppy Joe's Havana, Cuba

     Sloppy Joe’s literally marched across the street to its present location on May 5, 1937. The move was the result of a rent increase from three dollars a week to a whopping four dollars per week, a 25% increase that Josie Russell refused to pay.  Joe Russell paid $2,500 for the former Victoria Restaurant owned by Juan Farto at the time.  Built in 1917 Located at the corner of Duval and Greene streets, the Victoria had Cuban tile work, busily whirring ceiling fans, and jalousie doors.

     In true Key West fashion, the bar never actually closed during the transition–customers simply picked up their drinks and carried them, along with every piece of furniture in the place, down the block to 201 Duval Street. Service resumed with barely a blink. The new Sloppy Joe’s boasted the longest bar in town. Behind the bar, in the back room, were gambling and pool tables. Inside the bar hung life-size paintings of fighters on the walls, and adorning one wall was a 119-pound sailfish caught by Hemingway. Skinner had a place of pride above his new long curved bar. The bat Skinner used to control his patrons still hangs on the wall today.

     This bar still flourishes today at the same location.  Captain Tony’s Saloon occupies the original location on Green Street today.   Born on December 9, 1889, Josie Russell died of a heart attack at the age of 51 on June 20, 1941.