Murder victim owned Windsor’s Barb-B-Q roadhouse on Yonge Street, writes Susan Goldenberg

What all the Toronto newspapers called “Toronto’s First Gangland Murder” — the Jan. 7, 1939 shooting death of bookie/alleged racketeer Jimmy Windsor, 46 — had a North York connection.

Earlier that day, according to newspaper stories, Jimmy, appearing carefree, had sung barbershop quartets at the Windsor’s Barb-B-Q and Dine and Dance, a roadhouse he owned and his son Jack ran on Yonge Street just north of Sheppard, which at that time was countryside outside Toronto’s jurisdiction.

It was reported that Jimmy was killed as he was finishing dinner with his girlfriend and some relatives by four gunmen who burst into his home on upscale Briar Hill Avenue in North Toronto. Nobody else was shot.

Torontonians were stunned; the city had boasted it was “Toronto the Good.”

Jimmy’s murder was never solved. Donald “Mickey” McDonald, a local hoodlum, was convicted but reprieved because of shaky evidence. Afterwards, he committed so many violent crimes that he was called Canada’s Public Enemy No. 1.

Jack corralled Windsor’s employees to serve as pallbearers at his father’s funeral because nobody else would.

Jimmy had opened the business in 1936. It was legit; the police described it as “up-and-up.” But it had a rowdy reputation. After Toronto’s bars closed, the wild bunch roared up in their cars to Windsor’s to continue their revelry.

North York Chief of Police Roy Risebrough asked the local council to “blue law” it, the term for civic bylaws enforcing respectable public behaviour. Curfews of 11:45 p.m. on Saturday nights and 12:45 a.m. on weeknights were imposed and Windsor was ordered to remove the slot machines.

But the noise and brawls continued. “Fellows wanting the same girls; rivalry between city and country fellows,” Risebrough told the Globe and Mail after Jimmy’s demise. “A lot of fellows with their girls would get a skinful of beer in the Toronto beverage rooms and then come up here to eat and dance. It got a bad name, of course.”

He added, “There is no reason to believe there is a link to the shooting. The business is on the level. Windsor wasn’t up here much.”

Written by Susan Goldenberg.

Originally published on January 25, 2022, on toronto.com.