Bessie Starkman - 1889 or 1890 - 1930
Born Besha Starkman, Bessie Perri was the Prohibition Era Canadian high-profile crime boss. She originally married at 18 years old to Harry Tobsen, and the couple took in immigrant Rocco Perri as a boarder. Bessie left her husband, children, and Jewish faith to be with Rocco, and they moved to the Hamilton region of Ontario. Her first charges were for keeping a brothel, and Prohibition turned her and Perri towards bootlegging. Perri rose to the title of King of the Bootleggers, and he ignored mafia rules barring women, which allowed Starkman to rise through to the role of crime boss. The end of Prohibition caused their criminal enterprise to pivot to drug smuggling. She met her untimely end being gunned down in her garage in August of 1930. Her funeral procession was historically one of the largest Hamilton had, with 20,000 people estimated to have attended and a procession of cars longer than the 6 kilometer route from home to burial place.