Sam Bronfman
Bronfman (which literally means "whisky man" in Yiddish) rubbed elbows with a who's who of American mobsters.
It was Lucky Luciano who famously said that Bronfman bootlegged enough whisky to "double the size of Lake Erie." By the end of Prohibition, he had made $800 million, gone legit and purchased the Seagram's brand he's known for today.
Harry Hatch
Hatch purchased the Gooderham & Worts distillery in 1923 for $1.5 million. Soon after, he had an entire fleet of rum-runners (known as "Hatch's navy" ) in his employ.
He added Hiram Walker & Sons, makers of America's favourite firewater, Canadian Club, to the operation in 1926. By the end of Prohibition, he and Bronfman controlled close to two-thirds of the Canadian liquor trade.
John S. Labatt
John Labatt worked every angle to ensure his brewery survived Prohibition: He paid bonuses to bootleggers to get his product into the U.S., arranged out-of-province mail-order schemes and even produced 2% alcohol brews that complied with U.S. regulations. When the ban was lifted, a gang of disgruntled smugglers kidnapped him for ransom--but he managed to survive that, too.
John McLaughlin
McLaughlin is the Toronto pharmacist who stumbled upon "the Champagne of Ginger Ales" in 1904. Canada Dry, it later turned out, was the perfect disguise for terrible bathtub gin, and, by the 1920s, it was practically the official beverage of Prohibition. Unfortunately, it was an American man, P.D. Saylor, who reaped the benefits, having bought the Canada Dry brand in 1923.