Destin, Florida has a surprising amount of history with famous figures and significant events. Take a ride with St. George’s Transportation and we can tell you all about it, including the story of Al Capone’s connections to Destin.
During the midst of prohibition, a group of local business leaders in Tallahassee discovered that the notorious mobster Al Capone was passing through town. Despite his place on the FBI’s “most wanted” list, a small crowd (including a few police officers!) enthusiastically welcomed the gangster into the capital city. His ability to stay one step ahead of the law made him a bit of a folk hero in much of the country. As he passed the crowd, Al Capone simply rolled down the window of his black limousine and waved as they cheered wildly.
Al Capone
Although he was most known for his Chicago connection and frequent Miami vacations, Al Capone was no stranger to the Florida Panhandle. It was in the sunshine state that Capone liked to rest and escape the bitterly cold winters. He also used Florida as a place to hide out and lie low after various assassination attempts. Over time, it became an important part of his vast criminal empire.
The coast of North Florida was where his bootleggers would make landfall, on their long dangerous journey smuggling in spirits from the Caribbean islands.
“One of Al’s favorite recreation spots was Grayton Beach,” claimed Frank Pericola, Editor of the Panama City News Herald. The Valpariso Inn just past Fort Walton was another local joint he enjoyed visiting. But, Capone was always well behaved. The last thing the famous criminal wanted was too much attention while he was on vacation.
Although Al Capone purchased a massive 14-room Miami Beach retreat under his wife’s name for $40,000 in 1928, he was always moving around the state. He made countless road trips along both coastlines while his mansion was undergoing $100,000 worth of renovations, including the additions of a swimming pool, boathouse, and dock. According to local historian Tony Mennillo, one of Al Capone’s favorite travel destinations was the Emerald Coast, likely because it was also an ideal spot for bootlegging.
“It was desolate and hard to get to, and it was known for its moonshine,” said Mennillo.
During the 1920s, Destin was something of a retreat haven for bootleggers, including Al Capone. Just a few years ago, the Tampa Tribune had famously proclaimed the location Florida’s “Little Vegas” for its connections to illegal gambling. Locals say Capone would run liquor through the Choctawhatchee bay. There was a special train located in nearby Defuniak that traveled straight to Chicago. That coupled with the area’s many speculated waterways seemed to confirm a local theory that Capone hid a smuggling operation in plain sight.
According to the book, “Salty Memories Along the Coastal Highway” written by Tony Mennillo, many locals in Defuniak proclaim with absolute certainty that Al Capone, the legendary mobster, was there as a frequent vacationer. The stories go that a man nicknamed “Big Al” who possessed many of the same mannerisms as Al Capone was believed to be him on holiday throughout the 1920s and early 30s. Big Al had his own black limousine, not unlike the one described speeding on the streets of Tallahassee that was confirmed to belong to Capone. He had his own driver and could be found playing marathon rounds of golf on newly trimmed Bermuda grass.
Sometimes he would approach various locals to be his golf caddies for the day. The young men always accepted the offer because he was known to be a great tipper. After he got to know them a bit, he would identify himself as Al Capone. After golfing, Big Al would always take the young caddies back to his clubhouse for a beer. If the bartender declined to give the teenage caddies a beer, the rage of Capone would be felt.
He would yell, “They’re with me and I said get ’em a beer!”
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