Sloppy Joe's Bar and Ernest Hemingway

Famous Key West, Florida Watering Hole

R. M. Ziegler
This year Sloppy Joe's Bar will celebrate its 29th annual Hemingway look-alike Contest. The contest is held every July to pay tribute to the bar's most famous patron and resident of Key West, Florida.

Ernest Hemingway was a patron almost from the start, when the original owner, Josie Russell, ran a speakeasy during Prohibition. They met in 1928. Hemingway popped in to buy a bottle of scotch. A bank had refused to cash Hemingway's thousand-dollar royalty check, so Russell cashed it for him. The two men became close friends.

In 1932 Hemingway and Russell planned a two-week maritime holiday to Havana which ended up lasting two months. Russell owned a 32-foot cabin cruiser which he had used for over 150 rum running trips to Cuba. He charged Hemingway ten dollars a day to charter Anita. During their holiday, they met and hired marlin fisherman Carlos Gutierrez. He was an accomplished fisherman with forty years under his belt. Hemingway based old Santiago from The Old Man and the Sea on Gutierrez. It was also during that trip Hemingway discovered his passion for marlin fishing. He caught nineteen on that trip. Russell remained Hemingway's fishing companion for twelve years. He affectionately called him "Josie Grunts." Russell would be the model for Freddy, the owner of Freddy's Bar in his novel To Have and Have Not.

Prohibition officially ended on December 5th, 1933. On that day Josie Russell opened the Blind Pig, now a legitimate liquor business. The Blind Pig occupied the ground floor of a white frame house on 428 Greene Street. Russell leased the building for three dollars a week. It was a raucous place for gambling and shooting cheap whiskey. Russell renamed it the Silver Slipper after he added a dance floor adjacent to the bar.

According to Sloppy Joe's website, Hemingway deserves the credit for inventing the name we now know. One night he told Russell, "Joe, you run a sloppy place, you should call this place Sloppy Joe's." Then name stuck.

Hemingway was not the only legendary fixture at Sloppy Joe's. "Big" Skinner, a black man who tipped the scales at over 300 pounds, was Sloppy Joe's bartender for over twenty years. He is credited for creating Papa Dobles, a frozen daiquiri named after Hemingway. It contains rum, grapefruit juice, grenadine, club soda and lime. While Hemingway admitted to enjoying the drink on occasion, his drink of choice was Teacher's, a cheap brand of scotch.

One evening in 1936, a blonde girl walked into Sloppy Joe's with her mother and brother. Martha, or "Marty" as she was known, noticed Hemingway at the bar drinking scotch and wearing dirty dungarees. She paid Skinner twenty dollars to make an introduction. Hemingway would eventually leave his wife Pauline and make Martha his third.

In 1937 the landlord raised the rent to four dollars. Russell refused to pay the increase, and instead purchased the vacant Victoria Restaurant on the corner of Greene and Duval Streets where Sloppy Joe's remains today. He bought it from Juan Farto for $2500. The restaurant was originally built in 1917 and featured Spanish tile work, ceiling fans, and its famous curving wooden bar. It boasted to be the largest bar in town. A gambling room was added, and the bar displayed a 119-pound sailfish caught by Hemingway. The move to the new location did not interrupt Sloppy Joe's business. On the night of the move, patrons picked up their drinks and whatever fixtures they could grab, walked to the new location and resumed sipping their drinks. One fixture that did not make to the new location was a urinal. Hemingway had a fascination for it, so it got taken to his residence down the street.

Hemingway was at Sloppy Joe's almost daily, and the decade (1928-1938) during which he lived in Key West was one of his most prolific writing periods. He adhered to a strict writing schedule, rising at dawn and shutting himself in his pool house to write. Around three-thirty in the afternoon, he ambled over to Sloppy Joe's where he met his friends. Their group of regulars was nicknamed "The Mob." Among them were author John Dos Passos, Charles Thompson and Captain Eddie "Bra" Saunders. Charles Thompson was Hemingway's closest friend. He owned a hardware store and ran a fish house and cigar box factory. Karl from Green Hills of Africa was inspired by Thompson. "Bra" Saunders chartered local boats. He told Hemingway his life story which became the story, "After the Storm." John Dos Passos made an unflattering appearance in Hemingway's posthumously published memoir, A Moveable Feast. In it Dos Passos was referred to as "the pilot of fish." Hemingway also entertained out-of-town visitors at Sloppy Joe's. One such guest was his editor from Scribner's, Max Perkins.

Hemingway left Key West in 1938. The original owner, Josie Russell died from a heart attack in 1941, and the bar has changed hands several times. Hemingway's presence is still felt there even after all these years. Scores of visitors flock to Sloppy Joe's for a chance to sit at the same bar where Hemingway sat, shooting back scotch and spinning tales. The bar stays open 365 days a year and is open from 9:00 a.m. to 4:00 a.m.

Sources:
Sloppy Joe's Bar http://www.sloppyjoes.com

Carlos Baker, Ernest Hemingway: A Life Story (New York: Charles Scribner's Sons 1969).

Published by R. M. Ziegler

I've been writing for as long as I can remember. I wrote my first "novel" in second grade, a knock-off of my favorite book at the time, THE SECRET LANGUAGE. I've published a novel, short stories and articles...   View profile

Ernest Hemingway was credited with changing the name of the bar from the Blind Pig to Sloppy Joe's. Every July Sloppy Joe's hosts a Hemingway Look-alike Contest.

1 Comments

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  • Faith Draper 6/28/2009

    Excellent article, which I could be in Key West for the event - haven't been there in nearly 40 years but would love to go again sometime as an adult.

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