In the 1930s, Florida was a mecca for the Mob and the southern capital of America’s organized crime syndicates.

Gangsters from Chicago and New York would winter there, often under false names, splashing the cash they made in the post-Prohibition era from illegal gambling and sports betting. Some put down roots and invested in businesses and palatial homes.

Robert “Big Bob” McCullough was a henchman for Al “Scarface” Capone, the most notorious gangster of them all, and followed his boss to the Sunshine State.

Capone had bought a house in 1928 in Palm Island and lived there periodically with his wife and son. It was a useful bolt-hole. On the day of the St Valentine’s Day Massacre in Chicago in 1929, when seven members of his longtime enemy George “Bugs” Moran were machine-gunned to death by men dressed as police officers, Capone held a champagne party at his Miami home, providing him with witnesses who could testify to his whereabouts at the time of the murders.

As one of Capone’s most notorious enforcers, “Big Bob’” became head of security for the Miami Beach Kennel Club, a dog track that fronted Ocean Drive in South Beach. He was an investor in the Riptide Club, an upmarket nightclub in the Art Deco district of South Beach.

The Riptide was a classy joint and this Art Deco menu cover, which has a pearlized background, shows a stunning redhead surfing the waves while raising a glass of champagne.

“Big Bob” was often found at the bar in the Riptide or entertaining guests in one of the booths. He enjoyed champagne and the wine list has amazing vintages from the 1920s.

His name was linked to many crimes including the murder of a newspaper reporter. He also came under scrutiny in the murder of crime investigator William Drury who was slain in 1950 while parking his Cadillac in the driveway of his Chicago home.

He remained close to Capone until the gangster’s death in Palm Island – following his release from Alcatraz for income-tax evasion, in 1947. Capone had been suffering from a brain disease caused by syphilis, which manifested itself in tremors, jerking motions when he walked and paranoia.

“Big Bob” said he was in the room when his boss died and told friends Capone was “one of the finest men that ever lived.”

The mobster continued to go back and forth between Chicago and Miami and seems to have largely evaded the grasp of the law after Capone’s death. He died in a Miami nursing home in 1989 at the age of 97.

Courtesy Private Collection.

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