It’s a crime – in Leaside!

The first air mail delivery, Leaside Aerodrome.
The first air mail delivery, Leaside Aerodrome.

People often harken past to the innocence of the old days in their neighbourhood when everything was pure and ne’er a law was broken.

Yet while Leaside has definitely seen its recent share of traffic violations, theft, harassment, and mischief, its past hasn’t been completely devoid of criminal activity. In fact, quite the contrary.

Following on Geoff Kettel’s May article about the infamous Boyd Gang’s bank robbery in Leaside in 1951, this month’s true crime story looks back at the great prohibition years and the felonies committed during that era in our very own neighbourhood.

In 1916, the Ontario government passed the Temperance Act, which prohibited the manufacture, importation, and transportation of alcohol into Ontario. Leaside, along with the rest of the province, saw “dry days” until the repeal of the act in 1927. But, though a ban was in place, many people found creative, and sometimes nefarious means, of opposing, or even circumventing, the law.

In 1918, the first air mail delivery in Canada arrived in Leaside on a plane piloted by Captain Brian Peck. While Captain Peck had convinced his superiors at the Leaside Aerodrome to allow him to fly to Montreal to attract potential trainees to the British Royal Flying Corps working at the airfield in Leaside, Peck had an additional mission in mind. Along with his passenger, Corporal E. W. Mathers, Peck was determined to make the upcoming marriage of a fellow officer extra celebratory. Unable to purchase alcohol in Ontario, Peck and Mathers loaded up their plane in Montreal with a very heavy case of Old Mull Whiskey. With the extra weight causing excessive fuel to burn, the plane was forced to add extra stops to its flight plan. But the alcohol did make its way in to Leaside and the bootlegging mission was successful.

1919 saw a far more nefarious incident in one man’s plan to smuggle alcohol out of Leaside. On Monday, November 3rd, 1919, a taxi driver by the name of John Rolland picked up a fare at Union Station. The next morning, Rolland’s taxi was discovered near McRae and Bayview and Rolland himself stumbled to a nearby home bleeding profusely. Within hours, Rolland had succumbed to his injuries. According to a report in The Globe on November 8th, 1919, police were convinced that Rolland had picked up a man who was headed to Leaside to collect liquor which had made its way from Montreal. When Rolland discovered the purpose of the man’s trip, police believed that, unwilling to be a part of the crime, he refused the man’s request and headed back out of Leaside. It was at that point that Rolland was attacked and the murderer fled.

Lest you think Leaside has a history as a hotbed of criminal activity, our community has not been responsible for filling up the Don Jail over the years. In fact, it remains on the list of Toronto’s top 10 safest neighbourhoods. We’ll drink to that – with legal libations!


About Susan Scandiffio 154 Articles
Susan Scandiffio was born in Scotland and raised in Toronto. While she holds a master’s degree in history, her main passion (besides her wonderful family) is sports. Susan can often be found at the A.C.C. or in a Leaside arena or playing field, scoping out stories for Leaside Life.