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The Murder of Jimmy Windsor

(Saturday, January 7, 1939)

The murder of Jimmy Windsor, bookmaker and racketeer, on Saturday, January 7, 1939, frightened the City of Toronto as few other murders have ever done.

So far as the Toronto Police knew, Windsor was merely one of the city’s estimated 1,500 bookmakers, bigger than most, smaller than some. By reputation, in a dozen years of operation, he had not once been convicted of registering and recording bets. In August 1938, the police had raided Windsor’s home at 247 Briar Hill Avenue in North Toronto, but they found no evidence of anything illegal. According to Inspector of Detectives John Chisholm, James Windsor did not have a police record.

Windsor worked his handbook business from the White Spot Restaurant at 530 Yonge Street, a block south of Wellesley Street West.[1] He took few wagers directly and only accepted bets on horse races. He insulated himself by using runners who worked on commission to pick up bets at factories, barber shops, and cigar stores, where most of his “action” was actually placed. Six days a week, he would meet some or all of his commission men, usually at the White Spot, usually in the late morning. Information and money were guardedly exchanged over coffee or a light meal. If such a meeting lasted three quarters of an hour, it was a lot. This was in 1936, 1937, and 1938.

He was a dapper little man, jaunty of step, always well-turned out in a tailored suit and well-polished shoes. To a lot of people, he was “Mister Windsor.” Sure, he was friendly enough; he would toss off a “Hi, how are you?” to almost anybody who spoke to him, but that was usually the end of it, unless, of course, there was some business to conduct. He seemed, though, to badly want people to know he was doing well — or so some who knew him said, then and later. There was all the jewellery that he wore — a gold diamond-studded wristwatch, a diamond tie-pin, and a gold ring with a large diamond centrepiece. At times, he was indiscreet enough to flash a fat roll of bills in public. He seemed not to see the hungry eyes of some of his casual watchers or, if he did see, didn’t mind dangling his own success, real and imagined, before them.[2] This, in a Yonge Street walk-in-and-eat-for-15 cents restaurant, at the tail end of the Great Depression, when unemployment was everywhere, when wages were nothing, and relief was a bag of rolled oats and a few tins of whatever was cheap.

Saturday, January 7, 1939, was the last day of James Windsor’s 46 years of life. Before noon, he drove his 1937 Chrysler Imperial downtown from his North Toronto home and parked not far from the White Spot. Then, together with Lorraine Bromell, his 19-year-old live-in girlfriend, Windsor went in to collect from “Mr. Phillips” and one or two of his other bet runners. The restaurant clientele surely noticed, as before, Lorraine’s attractiveness, the manner in which she wore fine clothes, the jewellery she was dripping, and must have concluded, as at other times, that “Mr. Windsor” was a man of accomplishment.

In another compartment of his life, the bookie owned the Windsor Bar-B-Q, a barbecue-dance hall that his adult son, Jack, operated on Yonge Street north of Sheppard Avenue, in the suburban Village of Lansing.[3] This business, which opened in 1936, had acquired an unsavoury reputation due to noise and fighting around it late at night. After the tap rooms in the city closed at midnight, big cars full of men, including many Italians, often showed up there in search of whatever was on offer. On the recommendation of North York Chief Constable Roy Riseborough, the North York Township Council had recently “blue lawed” Windsor’s business.[4] Thus, an 11:45 p.m. closing on Saturday nights, and a 12:45 a.m. closing during the week, were now being rigidly enforced. The slot machines that Windsor previously had there had already been forced out. All of which meant the Windsor Bar-B-Q was leaking money badly.

This last day, Windsor made an afternoon call at the home of Morgan Baker, member of the provincial legislature for North York, in the Town of Stouffville. He went there asking for Mr. Baker’s help in getting a wine and beer license for the barbecue-dance hall. For a full hour, between 3 and 4 p.m., Windsor appealed to Baker, calmly, coolly, affably, while Lorraine sat alone, outside, in the Chrysler Imperial on a frosty January afternoon. He got nowhere. Baker spoke of the bookie’s “downtown business,” which he maintained was much-talked-about in Lansing, and said that North York already had too many licensed establishments. He advised Windsor to take the matter up with the liquor board himself.

Windsor’s last stop of the day was the barbecue. Whatever else he went there for, he took a few minutes to sing songs with his son, Jack, and two employees. “A regular barbershop quartet,” one of the participants later said.

At 7:20 p.m., James Windsor was comfortably seated at the kitchen table of his North Toronto home, in company with his two married half-sisters, Evelyn McDermott and Edith Warner; his young brothers-in-law, John V. “Jack” McDermott and Edward Warner; and Lorraine Bromell. The household was just finishing its evening meal when a loud knock came at the front door. Evelyn McDermott, nearest the hallway, was holding Edith Warner’s four-month-old daughter on her lap. She passed the child to her mother and went to answer the knock.

“Is Jimmy in?” a medium-sized man in a dark, close-fitting overcoat and a grey fedora hat asked when the front door to James Windsor’s home was opened.

Unsuspectingly, Mrs. McDermott admitted the man to the hall and was surprised when he was followed into the house by two others, one tall, one short, holding handkerchiefs up to their faces. The lead man, she was shocked to observe, carried a large black revolver in his right hand. He immediately began asking questions in a low, clipped voice: Where was Jimmy Windsor? Who else was in the house? Was there anybody upstairs? When satisfied that all in the house, especially Windsor, were in the kitchen, the man turned Mrs. McDermott around, put his right hand, which held the handgun, onto the now terrified woman’s shoulder, and shoved her along the hallway to the back of the house. He was by then holding a white handkerchief over the lower half of his face with his left hand.

The sudden burst of armed intruders into the kitchen caused all regular conversation to instantly come to a fearful halt. Pushing Evelyn McDermott aside, the lead man stalked briskly to the head of the table, pointed his big black revolver at James Windsor and coldly demanded, “Come on outside, Jimmy. Come out to the car.”

The bookmaker stared and said nothing.

The man repeated his instruction in a sharper tone. “Come on out to the car, Windsor,” he again threatened, flourishing the dark weapon in his right hand.

Windsor still did not speak. Lorraine Bromell would later say he seemed “stunned” by what was happening. To some others, he appeared to be assessing the situation. The previous evening he had discussed a recent rash of “shakedowns” of bookmakers in the city with Jack McDermott, who was 20 years his junior and much less streetwise. Possibly Windsor considered, as others would later, that the invaders were a gang of extortionists looking for “protection money” from a racketeer who could not easily go to the police. Jack McDermott was afterwards certain that “Mr. Windsor” would never sit still for anything of the sort.

“What’s this all about?” Windsor finally asked, calmly.

Looming over the bookie, the gunman said, “Come on, open up the box.” This was said only once. Then the same man, who was visibly growing angrier with each failed demand, instructed Windsor even more sharply, “Come out to the car.”

Then he put his hand, forcibly, on Windsor’s shoulder.

At this, James Windsor slowly started to rise from his chair. As he did so, he made the mistake of saying in a changed tone, “All right, you don’t have to get tough about it.”

The gunman did not hear this as compliance, as did some others in the room. Instead, as it seemed, he interpreted Windsor’s changed posture and the tone of the words he spoke as a threat to resist.

“All right, God damn you,” the man swore loudly, “Maybe this will bring you” — and he meanly fired the big black gun point blank at James Windsor’s guts. The shot made only a weak sound that was later described as both a “pop” and a “plop.” The bullet penetrated Windsor’s trousers below the third button of the fly.

It was right then, immediately after shooting Windsor in the groin, that the killer, according to the later testimony of all five eye-witnesses, took the handkerchief away from his face for a brief moment. Some said he put it in his left-side coat pocket.

Hit in the abdomen by a .455-calibre bullet that coursed downward into his left leg, severing his femoral artery, the bookmaker — according to later medical testimony — was doomed to bleed to death the moment he was shot. Still, he rose to his feet and staggered up against the kitchen stove where, with one blood-covered hand raised in the air, he weakly bleated, “Get me a doctor, quick.”

His two brothers-in-law at the kitchen table had jumped to their feet when the gunman fired. The women were screaming. Evelyn McDermott frantically pleaded, “Call a doctor. Don’t let him die.”

The sound of the hall telephone’s cord being ripped from the wall was an unseen member of the gang’s response to that plea.

Ever since the intruders first entered the kitchen, a second gunman, taller than the first, masked, wearing a peaked cap pulled down low over his forehead, had been wordlessly pointing a rusty-looking revolver at those at the table. This man was later variously described as having “lovely blue eyes,” “pretty blue eyes and nice eyebrows,” and “piercing blue eyes.”

“Keep quiet or you’ll get the same,” this pretty-eyed gunman now menaced the household.

Within seconds of being shot, Windsor, stricken as he was, was shoved towards the hall by the killer, who was being helped by a short, dark-complexioned man, who had flashed in from the hallway. This short man, barely noticed by most of the witnesses before this, dragged the bookie as the killer pushed him. The dying man took only three or four steps before he collapsed heavily in the hallway, just beyond the kitchen, his head hitting the cellar door with a thud.

There, on the floor, Jimmy Windsor was stripped of his jewellery and his pockets were gone through for what money he had. The man who shot him, not having gotten what he came for, began slapping and kicking Windsor while swearingly demanding not “the box,” but “the bag.” Windsor was past answering. The beating continued, the bookie being kicked repeatedly by the angry man who had pulled the trigger.

At real risk to herself, Lorraine Bromell bravely got up from the table and tried to stop the beating by getting the intruders what they wanted. When she couldn’t produce anything more, she too was kicked by the berserk killer, who at the same time ordered her back into the kitchen.

The short man in the hall was heard urging the others, “Come on, let’s go. Let’s get out of here.”

But the ugly scene went on and on — an estimated four to seven minutes from the first knock — before the killer in the hall called to the man in the kitchen, “Come on, Jim. We’re done here.”

There remained only the tall man with the “piercing blue eyes,” who then spoke for only the second time. “All right, upstairs,” he ordered forcefully, compelling the frightened family members, one by one, at gunpoint, to step over James Windsor’s body in the hall, then to go up the staircase to the second floor of the house. They did as they were told without looking back at the second gunman, whose footsteps followed them partway up the stairs, then waited there until they were out of sight.

In a few seconds, those on the second floor heard the sound of a car starting fast away from Briar Hill Avenue. When it died away, Jack McDermott called downstairs to make certain none of the gang still remained in the house. There was no answer. McDermott then telephoned the police on the upstairs extension.

Detective-Sergeant Harry Glasscock and Detective William Coleman, patrolling nearby in a cruiser, were literally at the door “in less than two minutes.” Their own call for detective assistance went over the police radio at 7:33 p.m.[5] Already the two detectives had bent over the dying man asking again and again, “Who did this to you, Mr. Windsor? Who did this to you?” Windsor’s only response was to mouth the word “doctor” two or three times. He lived a few minutes more, then gave a big sigh and passed away.[6]

A diagram of one of the most frightening murders in all of Toronto’s history appeared in the Evening Telegram of January 9, 1939. The drawing was captioned: “Invading his home at 247 Briar Hill Avenue Saturday night, one of four gunmen shot and killed James Windsor, operator of a North Yonge Street barbecue stand and dance hall. He was slain as he rose from a table in the kitchen to greet his ‘callers.’” Five adult members of Windsor’s family witnessed the killing. (The Evening Telegram)