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.

One of the Mob’s favorite watering holes was the Riptide Club, opened on November 16, 1936.

This upmarket nightclub, at 223 23^rd Street in the Art Deco district of South Beach, was grandly billed as Florida’s Smartest Cocktail Bar and Grill and A Rendezvous for Who’s Who in America.

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

The venue was opened by Billy Cook and his partners Harris Leveson and Steve Folsom.

Billy was an Italian immigrant from the Naples area who had changed his name from Roberto Castranova. He had Mob ties, and also operated a bar at 84^th and Amsterdam in New York in the 1930s. His brother Charlie was a big-time boxing promoter at Madison Square Garden.

Many gangsters and their molls enjoyed socializing at the Riptide and one of the regulars was Robert “Big Bob” McCullough, who was a henchman for Al “Scarface” Capone, the most notorious gangster of them all. 

This Mob enforcer, whose name was linked to many crimes including the murder of a newspaper reporter, was often found drinking champagne at the bar in the Riptide or eating the steaks, omelettes and Chinese dishes sent out from the kitchen and helmed by a chef nicknamed Curly.

We’re not sure when the Riptide closed but a relative of Billy’s told us an interesting story about the Riptide owner’s connections.

 When another member of the family opened a modest grocery store above his family’s living quarters in Youngstown, Ohio, his property was bombed when he refused to pay protection money to the Italian extortion racket called The Black Hand.

Billy heard about his relative's troubles in Ohio, intervened and the family was never bothered again.

Courtesy Private Collection.