Prohibition-era Montreal—a good-time town

March 5 | 2021

The 1928 Irving Berlin song “Hello Montreal” celebrated North America’s sin city, where cheap whiskey and illicit gambling were rife in the 1920s and 30s—the Prohibition era. My great-uncle Jockey Fleming, whose early history was said to be “rather fogged,” came of age in the city’s gambling dens and speakeasies. Yet as I tell in my recent memoir, The Smallest Objective, Jockey’s disregard for the law went well beyond sipping an illicit Tom Collins or Last Word. An early purveyor of fake news, Jockey made up his own story about his Montreal antics during the 1920s: He claimed to be a singing waiter, no less. 

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