Toronto, Chicago, Al Capone, Billie Holiday, Prohibition & the Winchester

Chicago mobster Al Capone made himself at home here.  Billie Holiday sang from the stage.  Hooks in the ceiling supported a trapeze used in burlesque acts, and some of the biggest entertainers of the 1920’s and 30’s played for the locals.

While MONTREAL was entertaining gangsters in its nightclubs and bars, staid TORONTO was busy making rye whisky at the huge Gooderham and Worts distillery on lower Parliament Street.

It was a natural fit for Al Capone and the mob.  Buy the booze in Ontario, transport it to Windsor, then through the Windsor-Detroit Tunnel, or on an intercity ferryboat, and onward to thirsty Americans.  At its peak, in 1928, Windsor-Detroit had anywhere from 16,000 to 25,000 speakeasies, blind pigs, clubs and joints.  The patrons were drinking booze made 250 miles east in conservative, church-going, teatotaling TORONTO.  The waterways separating Windsor and Detroit saw a huge part (one estimate: 75%) of the alcohol consumed in the United States during Prohibition.

<ABOVE – customs officers at work during Prohibition>

CAPONE6<ABOVE – Al Capone’s hangout – the Winchester Hotel bar in Cabbagetown>

One thought on “Toronto, Chicago, Al Capone, Billie Holiday, Prohibition & the Winchester

  1. Great piece. Have tried digging up info re: Capone in Toronto without much success. Do you have any real sources on this? Could you point me in the right direction? I am a journalism student and I’d like to look further into it. Thanks a bunch, Jeremy McRoberts

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