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Toronto’s first gangland murder in 1939 rocked the city, led to massive raids

James Windsor had just finished supper in his Briar Hill Ave. home with his two sisters, their husbands, 3-month-old nephew and an 18-year-old friend.

There was a knock at the door and one of the women opened it to a man in his late 20s with decaying front teeth.

“Is Jimmy Windsor in?” he demanded, marching her into the kitchen with a .45 automatic at her back.

Three more men followed him in as he spoke to the 46-year-old smoking at the table: “Come on out to the car, Windsor, we want to talk to you.”

As he rose from his chair, the gunman uttered, “Damn you, Windsor,” and pulled the trigger. As Windsor lay dying with a bullet through the abdomen, the assailant kicked him repeatedly. The intruders tore off about $ 3,000 worth of jewelry, including Windsor’s trademark big diamond ring, then ordered the terrified witnesses upstairs, ripped out the phone and fled.

The vicious killing on Jan. 7, 1939 was described by police in chilling detail as the eye witnesses told The Toronto Daily Star they feared for their lives because they could identify the attackers.

Called Toronto’s first gangland murder by the three major daily newspapers, the crime triggered the city’s biggest manhunt. Within minutes, the police force mobilized to raid suspected gang hangouts and gambling joints. Every detective was dispatched in an exhaustive investigation of organized crime that many considered long overdue.

“Dope and alcohol smuggling and bookmaking are the three largest enterprises of which racketeers are now allegedly seeking control,” The Star observed.

The month before Windsor was killed by a “gangland execution squad,” according to the paper, 32 local bookies had been robbed at gunpoint.

But in his book What Happened to Mickey? crime historian Peter McSherry notes Toronto police often ignored bookmaking, prostitution and other “consensual vices” as long as they didn’t lead to bigger problems or persistent complaints.

Still, rival gangs had been warring for years with a series of bombings, disappearances and shake-downs. Illegal gambling permeated every stratum of society from “professional men to day laborers” whose numbers and amount of money wagered were “decidedly staggering,” the paper said in 1923.

So pervasive was the problem that Toronto was identified as one of the biggest betting centres in North America by then-reporter Ernest Hemingway, whom The Star unleashed to do an investigative series.

Hemingway concluded that 10,000 people placed bets every day, mostly in the offices, factories or stores where they worked, generating an estimated $ 100,000 daily profit for illegal gambling organizations.

Jimmy Windsor played a role in this underworld, although what and how big was murky. With no criminal record, he was considered a “petty bookie-bootlegger” by police.

His lawyer, Thomas Elmore, called the dapper and fun-loving character a decent and generous man worth only $ 15,000 who didn’t have an enemy in the world. And yet someone slayed him in cold blood in front of his family.

Coverage of the case filled the papers for weeks as police sifted through various theories about the motive. Some sources said Windsor had refused to pay $ 25 a week for “protection” for his popular Yonge St. barbecue and dance hall. Police also investigated a report that the gunmen demanded payment of a $ 1,000 bet that Windsor had deemed “crooked.”

Others chalked up the crime to gang revenge and blamed Windsor for switching allegiances.

The Star reported that undercover cops believed chieftains of the gang world in Toronto, Hamilton and other cities along the Canada-U.S. border decided that “Windsor had it coming to him.”

During interrogations of underworld characters, “police began to untangle an amazing network of bootlegging, dope peddling and book-making activities,” the paper reported.

But it also aired grievances, including one from an anonymous official, that law enforcers weren’t doing enough to crack down on gambling and racketeering.

Even Buffalo police criticized Toronto cops for not collaborating with them even though the U.S. city had sinister types capable of the heinous crime and a tip had surfaced that three of the assailants had crossed the border to do the job.

“No crime in many years has challenged the police more than the Windsor case,” The Star observed. “Raid after raid was made on bootlegging establishments, known bookmaking places, and hundreds of clues were run down, many out of town,” paper said.

Police eventually learned the murder was a “climax to a shakedown robbery” when one of the four men shot Windsor during a surprise raid after realizing Windsor recognized some of them, TheStar said.

A break apparently came in connection with the disposal of the stolen jewelry and on Feb. 23, almost seven weeks after Windsor perished, police arrested two Toronto brothers.

Donald “Mickey” McDonald, 30, a known gang leader, who had been out on bail, and Alexander McDonald, 19, were charged with murder.

During their trial that spring, the younger brother was acquitted but Mickey was found guilty and sentenced to hang. Four days before his planned execution that September, he won an appeal after the court questioned much of the Crown’s evidence.

During a retrial, McDonald was found not guilty but was sent to prison to serve the remaining sentence for another robbery. Years later the man whom author McSherry dubbed Canada’s “public enemy number one,” escaped from Kingston Penitentiary and disappeared.

The man with bad teeth, who supposedly fired the fatal slug into Jimmy Windsor’s gut, was never caught.