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.
On the second floor of the Winchester Hotel in Cabbagetown (Winchester @ Parliament Street), the Winchester Kitchen & Bar, recently closed,was patterned after Old Chicago – rare in TORONTO bistros.
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>
<ABOVE – Al Capone’s hangout – the Winchester Hotel bar in Cabbagetown>