The legend of Sloppy Joe’s Bar, Key West’s iconic corner bar, started in 1933, but the place everyone knows today, in the building that stands sentinel at Duval and Greene streets, became what it is 85 years ago next month, on May 5, 1937.
Its official beginning was on Dec. 5, 1933 — the day Prohibition was repealed. The bar would go through two name changes and a sudden, legendary change of location before it would become the instantly recognizable Sloppy Joe’s that’s seen by millions of visitors to Florida’s southernmost outpost every year.
Even in the ’30s, Key West’s free thinkers looked on Prohibition more as an amusing exercise dreamed up by the government than any sort of official law, and Joe Russell operated an illegal speakeasy on Front Street in Key West.
When the government’s great experiment in sobriety ended as a dismal failure, Russell moved his business to a different Greene Street building and became a legitimate saloonkeeper as proprietor of the Blind Pig, a droll, rundown building that Russell leased for $3 a week.
Sloppy Joe’s migrated across the street to its present location on May 5, 1937. At the corner of Duval and Greene streets, the building had been built in 1917. Russell paid $2,500 for it.
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 St. Service resumed with barely a blink and has rarely stopped since (save for the occasional hurricane and pandemic).
The new Sloppy Joe’s boasted the longest bar in town. Russell, a native Key West Conch who was a rumrunner and charter fishing captain before he was a bar owner, died of a heart attack in 1941 at the age of 53, but the bar and its legend continued.
Sid Snelgrove and Jim Mayer purchased Sloppy Joe’s on Sept. 8,1978 and the bar still remains with the two families. Jean Klausing signed on as general manager in 1978 and remained GM emeritus until his death in January 2009.
While its history is older than 85 years, Sloppy Joe’s will celebrate 85 years at the corner of Duval and Greene on May 5, 2022.
“Each of us working here have a tremendous responsibility to continue the traditions of Sloppy Joe’s,” said Donna Edwards, brand manager for Sloppy Joe’s. “For 365 days a year we strive to give our customers the best party in town with live music on stage, great drinks, food and an awesome Sloppy Joe’s experience.”
Staff secrets
The Keys Weekly recently spent a morning with some of the bar’s longest-serving employees, who were eager to share some of the thousands of stories and memories the bar has prompted.
“There’s a lot that can’t be said to protect the innocent — and the guilty,” said Kit Crowl, who has been a server at Sloppy’s for 42 years. “But the two families that own this place make us all feel like a family. A lot of us really grew up in this place. We raised our kids together, you name it. We’ve always had each others’ backs.”
Similarly, Reta MacMackin has worked there 35 years and Julie LaMattina is right behind at 34 years.
“I’m one of the people who grew up here in Sloppy Joe’s, and I just hope I get out alive,” said Beverly Haddrell, who joined the staff in 1995, 27 years ago.
MacMackin and Crawl recalled the days before Sloppy Joe’s had its own kitchen and food service.
“Bob and Lucy, who eventually created Bobalu’s on Big Coppitt, used to sell fried bologna sandwiches out of a window up front. Before that it was a taco stand. Table service with actual food didn’t start until 1998,” LaMattina said. “Trust me, there were no salads on the menu back then.”
“We used to have quite a crew that came in whenever we would open at 9 a.m. each day,” MacMacken said., “We had the cocaine cowboys who hadn’t been to bed and the early daytime drinkers who would stop in before work.”
“I remember dancing on the bar one night with a bottle of Jack and I don’t even drink,” LaMattina said.
But beyond the wild times, there’s been an unending sense of friendship and camaraderie for decades. “Our staff has made friends from all over the world who come back year after year,” Haddrell said.
The staff fondly recalls their favorite Hemingway Look Alikes, and chuckle at the newer employees who can’t tell any of them apart.
“They’ll look at me with wide eyes, and ask, ‘How do I run tabs for these guys? I don’t know who’s who,’” MacMackin said.
Charles Fraga, who’s been a barback at Sloppy Joe’s for 20 years, summed up the place nicely.
“It’s such a dichotomy, because to us, we’re all a family, the staff, the owners and it’s a family-run business. But it’s one that’s internationally known. Our T-shirts are probably in every country of the world by now.”
