April 23, 1944
Self-styled as “Canada’s greatest bootlegger”, Rocco Perri was brazen about the title. He would hold court in his home in Hamilton, Ontario, granting interviews to newspapers and flaunting his position to the cops. And what’s more, he was able to get away with it.
The thing was that though Perri admitted to being a bootlegger, that admission alone was not enough, under Canadian law, to put him behind bars. The cops required some proof; Perri had to be caught in the act in order to make the charges stick. During the 1920s that just hadn’t happened. Though Rocco did a little time in 1927 for perjury, there wasn’t much more than that to bring him in.
It’s hardly remembered today, but a form of Prohibition existed throughout the late teens and into the 1920s in a number of Canadian provinces. The problem, at least as far as the temperance organizations were concerned, was that the ban was not nationwide. Certain provinces, such as Quebec, voted Prohibition down pretty sharply, while the provinces that did maintain it had a confusing array of laws in place that allowed for loopholes and, frankly, defiance. Perri took advantage of these slim regulations and shipped the good stuff not only into the United States, but sold it in Canada as well, making double the money.
Perri’s partner in crime in all this was his common-law wife, Bessie Starkman, a formidable woman who was one of the few females to hold sway during the heyday of organized crime. Some claim that she was the actual force behind the throne of the Perri empire, that Perri rarely acted without her instructions.
This seems unlikely, however, as Bessie was thoroughly disliked by the Perri goons, and lacked the finesse, charisma and people skills to run the Perri organization. Bessie was so disliked in fact that on August 13, 1930, she was killed, probably by members of the Perri establishment. Perri, heartbroken and almost collapsing at the cemetery, gave Bessie a lavish send-off worthy of any mob boss of the period. And then he went right back to work.
Throughout the 1930s Perri aligned himself with another strong woman, Annie Newman, and branched out into extortion, gambling and other rackets. But it would be the Second World War that finally took the wind out of his sails. Frank Zaneth, an operative in the RCMP who had been hounding Perri for years, was at last able to apprehend the gangster under the War Measures Act, arresting him as a suspected Fascist and enemy alien. It was an excuse, of course, a loophole that allowed Zaneth to bring the mobster in. Perri was well acquainted with loopholes.
He didn’t get out again until 1943, and like so many other mobsters before him, found that things had changed since he’d been in jail—Petawawa this time. For one thing, the Buffalo family—the Magaddinos—had expanded their territory into Perri’s old stomping ground of Hamilton, Ontario.
So on the balmy spring morning of April 23, 1944, Perri went out for a walk, and was never seen again. Some said he had just “disappeared” himself, and actually survived into the early 1950s. It’s more likely, however, that Perri was given cement overshoes and is currently residing at the bottom of Hamilton Bay. The Magaddinos then had nothing to worry about.