Whiskey through Prohibition
There's a lot to say about Hiram Walker's Canadian Club when it comes to Chicago history. The East Douglas, Massachusetts native moved to Detroit, Michigan in 1838, and started his distillery 20 years later in 1858. When Prohibition (1920-1933) became an inevitability, Walker relocated the business across the Detroit River to Windsor, Ontario. He still lived in Detroit, so he commuted back and forth through a private tunnel under the river.
Walker's whisky did well in Canada as liquor was still legal, but the real money was from bootlegging, and Hiram made a considerable amount of money selling to gangs based out of Detroit including the infamous Purple Gang.
It is at this point in the story where we cross over into folklore - it's an area that is muddled by incomplete police work, skeptical evidence, and a tsunami wave of bragging hitting against the solid rock coast of denial.
But this is what we do know: After the St. Valentine's Day Massacre (1929) in which seven members and associates of Chicago's North Side Gang were murdered, the Purple Gang were no longer able to bootleg whisky. The person who took over for them was a member of the North Side Gang's rival to the south... Al Capone.
In 1933, Prohibition had ended in the United States, and Hiram Walker could sell liquor as a clean business with freedom to advertise. In the first part of this incredible video below, you can catch what it was like driving down Michigan Avenue over 80 years ago. (Spoiler alert, not much has changed.) It's fascinating to catch what we now consider "antique advertising" when it was in its proper place in history, nestled as contemporary. Right at the 20 second mark of the video, as the vehicle pass Washington Street, you can see Hiram Walker's Canadian Club. It apparently did very well for him as he duplicated this at Times Square a few years later.
How about a drive?
This Canadian Club sign is exactly 3 miles south from the St, Valentine's Day Massacre that led to the famous union between Hiram Walker and Al Capone. This video is found at the Flat-Spot's YouTube channel.