When one thinks of Al Capone, images of Chicago's bustling streets, clandestine speakeasies, and notorious gangland activities come to mind. However, the infamous gangster also had a significant chapter of his life set against the sunny backdrop of Florida.
Alphonse Gabriel "Al" Capone, better known as Scarface, was one of the most notorious gangsters of the 20th century. Born in Brooklyn, N,Y., on January 17, 1899, Capone was the fourth of nine children in an Italian immigrant family. His father was a barber, and his mother a seamstress—hardworking folks who probably didn’t expect their son to become America’s most famous mob boss. But young Al had other plans.
He joined the notorious Five Points Gang in Manhattan, where he worked under gangster Frankie Yale. In 1919, Capone moved to Chicago to assist Yale's associate, Johnny Torrio, in managing illegal enterprises during Prohibition. After Torrio's retirement following an assassination attempt in 1925, Capone took over as the head of the Chicago outfit, expanding its operations in bootlegging, gambling, and prostitution, according to the Federal Bureau of Investigation.
Seeking refuge from the violent gang wars in Chicago and desiring a retreat, Capone purchased a mansion at 93 Palm Avenue on Palm Island, Fla., in 1928 for $40,000. This waterfront property served as both a sanctuary and a strategic base for his operations. (The Miami Beach property has since been demolished).
Notably, during 1929 St. Valentine's Day Massacre, where seven members of a rival gang were murdered in Chicago, Capone claimed to be at his Florida residence, providing him with an alibi.
Florida's extensive coastline and proximity to the Bahamas made it an ideal hub for smuggling illegal alcohol into the United States. Capone capitalized on this by establishing bootlegging routes through South Florida, ensuring a steady supply of liquor to meet the nation's illicit demands. In the late 1920s, Capone and his associate Johnny Torrio acquired land around Gulfport, near St. Petersburg, to facilitate their smuggling operations from the Gulf of Mexico, according to Floridaman Media.
Al Capone was frequently spotted at the Gangplank, later known as Jungle Prada Tavern, the first nightclub in the area, according to the St. Petersburg Historical Society.
The Gangplank was a speakeasy that opened in 1924 in a neighborhood known as “The Jungle.” It was perfectly positioned for Prohibition-era bootlegging. Situated on Boca Ciega Bay, an infamous rum-running hotspot, it was conveniently located next to a boat ramp, allowing shipments of illicit liquor to be discreetly offloaded under the cover of darkness. While guests enjoyed top-tier entertainment from artists like Duke Ellington and Nat King Cole, local bootleggers used the club as a covert meeting spot. Patrons were allegedly served alcohol in teacups to maintain an air of respectability, while the nearby bay ensured a steady flow of spirits into the city, according to the Mob Museum.
Capone's was also linked to a fish packing house in Deerfield Beach, which allegedly functioned as a front for a gambling casino, brothel, and a hub for shipping illegal booze. In 1930, he purchased a 56-acre tract of land, known today as Deerfield Island, with plans to construct a $250,000 residence, further cementing his ties to the region.
Despite his attempts to establish a base in Deerfield Beach, Capone faced significant resistance from local authorities. In April 1930, he was arrested on vagrancy charges while visiting Miami Beach, following orders from the governor to expel him from the state. Capone claimed mistreatment by the Miami police, leading to a perjury charge, though he was acquitted after a three-day trial in July.
Capone's reign began to wane following his 1931 conviction for tax evasion, resulting in an 11-year prison sentence. After serving time in Alcatraz and other prisons, he was released in 1939 due to deteriorating health from neurosyphilis. He spent his remaining years in his Palm Island home, leading a secluded life until his death on January 25, 1947, from cardiac arrest following a stroke.
Today, Capone's Florida ventures are emblematic of the state's complex history during Prohibition, reflecting both the reach of organized crime and the challenges law enforcement faced in curbing illicit activities.
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