Rocco Perri was called “Canada’s King of the Bootleggers” and “Canada’s Al Capone.” He was also one of the most fascinating characters in the colourful history of North American organized crime. Perri was the head of the Calabrian mob in southern Ontario and his right-hand person, was his common-law wife, Bessie Starkman, the only Jewish woman in history to command an Italian mob.

Rocco started out in the mob neighborhoods of Hamilton, Ontario and created a booze empire that stretched in the United States. While other mobsters shipped booze south by boat along the coast, Rocco laundered his liquor as turnips and sent boxcar loads south to New York and west to Chicago. He made deals with the pillars of the Canadian establishment. Selling liquor to the United States from Canada wa perfectly legal here–but it took Rocco and Bessie Perri to send it on its way. Strangely although it was legal to manufacture and export the stuff, it was illegal to sell it in Ontario, so Rocco doubled his profits by “reimporting” some of it back into Ontario.

In the late 1920s, Rocco and Bessie moved into the narcotics racket and used their connections in New York, New Jersey and Philadelphia to sell the drugs. But Bessie was growing arrogant and one night in 1930, she was ambushed by two hit men in the garage of their Hamilton home and killed with two shotgun blasts.

Rocco kept up the rackets and in the mid-1930s he was on top of the game again, again with a strong Jewish woman by his side, Annie Newman. With Prohibition over in the United States, but government controlled liquor stores in Ontario, Rocco used his old Chicago connections to create a Prohibition-in reverse racket, smuggling booze into Canada from the windy city. And throughout his career, Rocco was dogged and tracked by the RCMP’s Operative No. 1 Frank Zaneth. Zaneth finally got Rocco, at the beginning of the Second World War, under the War Measures Act.

Rocco disappeared soon after he was released at the end of the war, and it is believed that he’s in a barrel of cement at the bottom of Hamilton Bay.

Dubro and Rowland have done an absolutely stunning research job…Who says all the snappiest mobsters of that era were American?-Toronto Star

Photo:Archives of Ontario

Out of Print (after ten years) in May 1998