The official beginning of Sloppy Joe’s Bar, the famous and infamous Key West Saloon beloved by Ernest Hemingway, was smack in the middle of the Depression, December 5, 1933, the day Prohibition was repealed. But the bar was destined to go through two name changes and a sudden change of location before it would become today’s Sloppy Joe’s Bar seen by millions of visitors to Florida’s southernmost outpost.
In Key West, a bastion of free-thinkers even in the thirties, Prohibition was looked on as an amusing exercise dreamed up by the government. Joe Russell was just one of the enterprising individuals who operated illegal speakeasies; his being a raunchy hole in the wall on Front Street near the harbor. Even Hemingway slipped over to Russell’s on occasion to buy illicit bottles of scotch.
Joe Russell was a Conch born and raised in Key West. Conch is the name given to Key West natives; a name that derived from that of the tough, tasty mollusk found in the waters surrounding Key West. Russell a charter boat captain who ran a 32-foot cruiser called the Anita, eventually became Ernest Hemingway’s boat pilot, and was the author’s fishing companion for over twelve years. In his company, Hemingway once caught and astonishing 54 marlins in 115 days.
Joe knew the Cuban waters like he knew his own skin and not just for their fishing potential. He was one of the daring rumrunners in the Florida Keys, thriving on the rush that came from making a successful run across the night waters; playing games with the Federal agents; dodging in and out of the tiny bays and inlets around the Keys.
Russell was far from being the only rumrunner in the Keys during the Prohibition era. After all, it was the Depression. Times were hard in Key West, and good liquor sold for forty dollars a case up north. It wasn’t legal by any means, but a man had to feed his family. More than one islander, who could drive a boat made the trip from Key West to Havana on a regular basis, bringing back nothing but the best in whiskey and rum.
Between rum running and operating a speakeasy, Joe did pretty well for himself during Prohibition. By the time the Volstead Act was repealed in December of 1933, he had squirreled away enough money to open a legitimate business.
Located at 428 Greene Street, the Blind Pig was a door-less run-down building that Russell leased for three dollars a week. It had sawdust on floor, pools tables, and gambling. The prevailing attitude was “come as you are and stay as long as you want,” literally, since it was open twenty-four hours a day.
It was a free-wheeling fisherman’s bar featuring ten-cent shots of gin and nickel beer. No matter what kind of scotch whiskey a customer requested, he was generally served a measure of Teacher’s, the cheapest brand around at thirty-five cents a drink. The rowdy, come-as-you-are saloon, was renamed the Silver Slipper upon the addition of a dance floor, but that didn’t matter, it remained a place of shabby discomfort, good friends, gambling, and fifteen-cent drinks.
The place might not have been fancy, but it was home to Joe Russell and his crowd for three and a half years.
That crowd included (and, in great part was centered around) Ernest Hemingway. Captivated by Key West’s rowdy atmosphere and spectacular fishing, Hemingway was the first famous author to make the island his home.