Historicist: Toronto's First Gangland Murder
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Historicist: Toronto’s First Gangland Murder

The brutal death of bookie Jimmy Windsor shocks Toronto in 1939

The Toronto Telegram, January 9, 1939.

On the evening of Saturday, January 7, 1939, restaurant owner and illegal bookmaker Jimmy Windsor was just finishing his dinner along with his two half-sisters, their husbands, and his own girlfriend at his home at 247 Briar Hill Avenue. Following a knock at the door, Windsor’s half-sister Evelyn McDermott unwittingly admitted four men into the house who headed straight for Windsor, their faces reportedly hidden by handkerchiefs. After a brief exchange of words, the lead intruder produced a gun and began issuing Windsor instructions. When Windsor was slow to respond, he was shot in the groin and pushed toward the hall, relieved of the valuables on his body, and his body savagely beaten. The four unknown assailants soon fled, leaving Windsor to die in his own home. The next Monday, all three Toronto newspapers reported Windsor’s murder as the city’s first “gangland killing.”

Toronto’s underground betting culture had been well known for some time. In 1923, Ernest Hemingway wrote a feature on Toronto’s illegal gambling community for the Star Weekly, claiming that 10,000 people then placed bets in Toronto every day. Although Hemingway outlines a few betting scenarios in this piece, he noted that “the bulk of the bookmaking betting done in Toronto is done right in the offices, factories, or stores. Every office or building where any number of men are employed has its own bookmaking agent.”

By the late 1930s, illegal bookmaking was flourishing, and had led to some operations that were much larger and more organized. Jimmy Windsor had apparently operated as a bookmaker since the late 1920s, doing his business out of the White Spot Restaurant on Yonge Street, near Wellesley. Although known to the Toronto police and subject to at least one police raid, he had managed to stay out of trouble with the law, limiting his bookmaking to horse races, and usually receiving bets through agents rather than directly from the bettors. In What Happened to Mickey?, Toronto crime historian Peter McSherry notes that at this time, Toronto police often turned a blind eye to bookmaking and other “consensual vices… so long as they did not lead to bigger problems or there were no complaints that were persistent or could not otherwise be smoothed over.”

The Globe and Mail, January 9, 1939.

This laxity evaporated in the days following Windsor’s murder. There were no clear leads to either the motive or the identity of the assailants. Suspecting the murder was connected with the city’s underworld, the police began searching all the favourite locations of Toronto’s criminal classes. According to the Telegram, “gambling joints in the city and suburban area, poolrooms, and bootleggers were visited by detectives and, one by one, the men picked up began to arrive at [police] headquarters for questioning. The parade continued all Saturday night and all day Sunday.”

The newspapers circulated descriptions of the four wanted men as per the five eyewitnesses, although these were quite vague. None were said to be likely more than 30, and all four were described as having darker complexions. Windsor had evidently had some trouble from some Italians at his legitimate business, a dance hall called the Windsor Bar-B-Q, located near Yonge and Sheppard; this likely led to the suggestion that the gang of killers may have been Italian.

The media offered various theories as to the motive of the crime. Although Windsor was relieved of some valuable jewellery he had on him, it was not seen primarily as a robbery, as the men made no apparent effort to take other items of value which were in plain sight. The first theory to hit the newspapers was that Windsor had refused to pay money to a protection racket, with the suggestion that this racket was more of a problem in Toronto than had been previously believed. The Telegram wrote that “it was found that although tribute had been exacted and paid by many of the lesser fry of bookmakers and bootleggers, that the gang preying upon them were having more difficulty with the larger operators. According to the theory now held by the chief police investigators, the brutal murder was the gang’s way of telling them what they could expect.”

Scenes from Jimmy Windsor’s funeral. The Toronto Telegram, January 11, 1939.

A few days later, the Star reported on a tip suggesting that Windsor’s killers had come up from Buffalo specifically for the job, the motive being that Windsor had double-crossed a powerful gang. The Star continued trying to promote this theory, criticizing Toronto police for not working more actively with the Buffalo police and exploring this possibility. On January 16, they quoted Buffalo’s assistant chief of detectives as saying “we have several characters in Buffalo who are quite capable of the brutality that accompanied the killing… We are aware of a link between various rackets, including bookmaking and alcohol-running on both sides of the border.”

After a few weeks of speculation, no arrests had yet been made in Windsor’s murder. Several known Toronto underworld figures had appeared in police lineups before the five witnesses, but none had yet been identified. According to Peter McSherry, “the five eyewitnesses to Windsor’s death had made a secret agreement among themselves not to identify anyone in the line-up room,” lest a positive identification lead to their own murders to prevent them from testifying. As it was, the five witnesses to the murder remained under police protection at the Briar Hill Avenue house, reportedly afraid for their lives, and all three newspapers reported on the culture of fear that pervaded amongst all those who attended Windsor’s funeral.

The lack of an arrest made the Toronto media restless. All three newspapers, hungry for action, issued calls for the local police to clean up the gangs. One Globe and Mail editorial wrote that the murder was “symptomatic of the rotten condition that has been allowed to develop in Toronto. Its ramifications reach to other centres of the province, and apparently tie in with the mobsters in the United States.” Expressing the need for immediate action, the editorial added that “this city is not going to be made into a little Chicago by a crowd of tinhorn thugs.”

Evidence seized on an illegal bookmaker’s in Swansea. The Toronto Telegram, January 13, 1939.

In the week after Windsor’s murder, local police raided several larger betting establishments, both in Toronto and in the surrounding municipalities. One tip led to a raid of a parlor in Swansea, located above the Kingsway Pharmacy on Bloor, near Jane Street. The Globe and Mail wrote that “police are confident that it was the biggest bookmaking clearing house that has ever been uncovered in the province,” yielding eight arrests, 20 different telephones, and evidence that “the average betting for from one to three days would be $10,000.” Swansea’s police chief would later be fired after it was revealed that he had known about this bookmaking operation for several months, yet failed to act.

Toronto finally got some closure on the Windsor murder on February 23, when police formally charged Donald “Mickey” McDonald. McDonald had, in fact, been in custody for several weeks for his role in the assault and robbery of a Church Street bootlegger named James Elder. Out on bail during the time of the Windsor murder, he had subsequently been convicted for his role in the Elder case, and sent to Kingston Penitentiary.

Police were tipped to McDonald’s role in the Windsor murder by Jack Shea, an established criminal facing charges for a Port Credit bank robbery that he had executed with McDonald’s brother the previous December. Shea provided the police with some hearsay evidence, which led to McDonald’s inclusion in a lineup. The witnesses’ identifications of McDonald were imperfect to say the least, but apparently good enough to proceed to trial. For the Toronto media, however, the Windsor murder appeared to be solved, and attention soon shifted to Mickey McDonald.

Courtroom sketch drawn by Charles R. Snelgrove. The Toronto Telegram, February 24, 1939.

Although initially convicted, McDonald was able to successfully appeal following several irregularities, and was acquitted at the ensuing retrial. Having apparently escaped justice for one of Toronto’s most notorious murders, Mickey McDonald soon acquired a reputation as one of the country’s most notorious criminals. This reputation only grew when, while imprisoned for a truck hijacking, McDonald was part of a 1947 escape from Kingston Penitentiary. A few days after the escape, he and his two fellow escapees successfully held up a bank in Windsor.

Although both his confederates in escape were eventually found, McDonald was never positively identified again. In 1950, the Telegram quoted an unnamed Toronto police official as stating that the police “believe that Mickey was rubbed out by his own gunmen associates.” The article also claims that “Letters sent to local hoodlums from McDonald associates in the United States also tell of his violent death.” Over subsequent years, stories from the underworld repeated the assertion that McDonald had died, although accounts often disagreed on the location and the circumstance. By 1955, the belief that McDonald was dead was evidently shared by those in his old Toronto neighbourhood. The Globe and Mail’s Phil Jones interviewed people with connections to McDonald, and found someone who claimed McDonald was buried in New York after interfering with an established “dope racket.” “Officially,” Jones wrote, “Mickey is still alive. He will remain that way until his body is found. But to Jarvis St. he is dead.”

Additional material from: the Globe and Mail (January 9, January 10, January 11, January 12, January 13, January 14, January 16, January 25, February 17, February 24, February 25, 1939; January 6, 1955); Peter McSherry, What Happened to Mickey?: The Life and Death of Donald “Mickey” McDonald, Public Enemy No. 1 (Dundurn, 2013: Toronto); the Toronto Star (January 9, January 10, January 11, January 12, January 13, January 14, January 16, January 17, January 18, January 20, January 25, January 27, February 1, February 3, February 24, February 25, 1939); Star Weekly/em> (December 29, 1932); the Toronto Telegram (January 9, January 10, January 11, January 12, January 13, January 14, January 17, February 16, February 17, February 24, 1939; March 27, 1950; December 11, 1952).

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