by Brian Vallee
John Clement was a law student from Niagara Falls and would later serve as a provincial cabinet minister. “We used to gravitate to the pool rooms when we were home for the summers,” he recalls. “Rocco’s was one of them, and I think I was nineteen or twenty the first time I saw Lennie. He was a pool shark, but he wasn’t a punk who hung around there all the time. He would just come in for a Coke and a game of snooker. The street I lived on was in sort of the posh area of town and you were proud of yourself for knowing somebody like Lennie – from the other end of town. He was five or six years older than us and we considered him very cool. He was a nice guy – never loud or pushy. He’d been overseas, and he’d been hurt – he was cool.”
Lennie decided he needed a career to support himself. He took a six-month course in hairdressing and started his new career working in his mother’s shop. He stayed at hairdressing for several months, but was soon bored, and the long hours standing on his artificial foot were painful. This wasn’t how he wanted to spend his life. He moved to Toronto once again, and this time found work at the Horseshoe Tavern.
Jackson’s sister, Mary Mitchell, was separated from her husband and working as a model and part-time hostess at the Holiday Tavern a few blocks west of the Horseshoe. While working a modelling job in Windsor, Ontario, she met another model, a young Englishwoman named Ann Roberts. Ann was from the north of England and had immigrated to Canada with her husband at the end of 1947. They settled in Toronto, where their marriage soon ran into trouble. In June 1948, when she was twenty-one, they legally separated, with Kenneth Roberts suing for divorce on grounds of adultery. She did not contest the divorce, and it was granted in May 1951.
Lennie was shy around women, and Mary suggested she could introduce him to Ann. “I’ll choose my own girl,” he snapped. Then, in May 1950, Ann happened to be walking along Queen Street West when she bumped into Mary and Lennie near the Horseshoe. “I fell in love with him that first day,” she would say later. At five-foot-nine, Ann was almost as tall as Lennie. She was soft-spoken, and he was captivated by her English accent and quiet charm. He asked her out the next night, and they kept steady company for the next four months.
Lennie had mastered his artificial foot and was comfortable going out in public. “Don’t believe the stories of witnesses who claim they could recognize Leonard by his limp,” said Ann. “It just wasn’t so. I went out with him for two weeks before I found out about his wooden foot. And then it was only because his sister told me.”
By September 1950 Lennie and Ann were living together in an apartment on Sackville Street in downtown Toronto. She worked as a model, and he continued working at the Horseshoe. But it wasn’t long before Lennie Jackson decided he wanted some of the better things in life, and that the way to get them was not by waiting on tables in a bar, but by robbing banks. To line up accomplices, he didn’t have to look any farther than big-tipping Frank Watson.
On February 27, 1951, two men entered the Canadian Bank of Commerce in the village of Pickering, just east of Toronto, a few minutes before closing time. There were no customers in the bank. The men were carrying brown paper bags with revolvers inside. They rattled the bags to get the attention of the six bank employees, including the manager, Neil R. Shortreed, who had his back to the door when the bandits came in. “I looked around and saw one of the men taking a gun out of a bag. He pushed it into one of the girl’s faces and demanded money.”
The junior clerk, Helen Butt, and senior clerk, Mary Riley, were standing behind the counter towards the rear of the bank, as was Shortreed. They saw that both men carried handguns. One of the men entered the manager’s office and came out a side door behind the counter. Crouching, he pointed his gun at the bank employees.
“Get down on the floor,” he ordered. Helen Butt complied, but Shortreed noticed that the floor was dirty. “I had my good suit on,” he told police later, “so I sort of backed into an area below a table where there was a shelf, and sat on that, facing out into the bank.”
He watched as the man who had come behind the counter entered the teller’s cage and emptied the cash drawer into a large, heavy canvas bag he had with him. “I saw him take the bills, and even the silver.” The robber also took a bank-issue .38-calibre Ivor Johnson revolver. He then walked back to the vault and motioned to Shortreed to join him. On his way to the vault, the manager stepped on the floor alarm.
“Open it!” ordered the robber, his gun at the manager’s back. Shortreed fiddled with the dial of the combination lock, stalling for time. Seconds later the phone rang, and when he reached around the vault to answer it, he saw that both men were gone. Helen Butt and Mary Riley both got a good look at the man giving the orders – the apparent leader. “I would never forget his eyes,” said Riley. Later she and Helen Butt would pick him out of a police line-up. The man they pointed to was Leonard “Tough Lennie” Jackson. The eyes, said Riley, were unmistakable.
Two weeks after the robbery, Ann Roberts and Lennie Jackson moved into an apartment on Lumsden Avenue in the Danforth-Woodbine area, a few blocks north of where Ed Boyd grew up.
On March 27, 1951, three men, one armed with a shotgun and the others with revolvers, entered the Canadian Bank of Commerce in Colborne, eighty miles east of Toronto, just before closing time and walked out with about $5,000. A fourth man was waiting in a getaway car parked in front. The Haldimand Township clerk, Max Rutherford, one of ten customers in the bank, refused to lie on the floor with the others and grabbed the barrel of the shotgun. The robber wrenched it free and struck Rutherford over the head. When the bank’s manager, R.J. Virgin, told another of the bandits that he didn’t have the keys for the vault, he was struck on the head with a revolver, suffering a two-inch gash. The robbers escaped in a late-model car with stolen licence plates and eluded roadblocks that the OPP had set up on all the main roads around Colborne.
That robbery came just a week after Edwin Alonzo Boyd robbed the Armour Heights branch of the Bank of Montreal for the second time. The Colborne robbery made the front pages of the Toronto dailies, but the robbers didn’t get the headlines that Boyd was getting. That would soon change when Boyd took the summer off to work on his Pickering house.
Six weeks later, on May 10, 1951, three armed men held up the Royal Bank at Woodbridge, just northwest of Toronto, escaping with about $4,000. Adopting Ed Boyd’s tactics, one of the bandits vaulted the counter to rifle the teller cages. Two customers followed the robbers out of the bank hollering “Hold-up! Hold-up!” and had to dive for cover when they were fired at as they tried to get close enough to read the licence number of the getaway car. The police set up roadblocks at the western entrances to Toronto, but once again the robbers escaped.
The roadblocks went up again two weeks later when two gunmen held up the Mitchell branch of the Canadian Bank of Commerce, thirteen miles northwest of Stratford, escaping with $8,000. Both men carried .45 calibre revolvers. On their way out with the cash, they also stole one of the bank’s guns. The manager, A.G. MacDougall, said he knew it was a hold-up the moment he saw the two men enter the bank. “I went into the vault and closed the inner door and they didn’t see me,” he said later. “They were young fellows, one wearing dark glasses and one a bandanna. They cleared out the cash drawers of three of the tills.” This time the Toronto dailies gave the robbers their full attention with headlines rivalling those of Boyd’s early robberies.
By this time Lennie Jackson had quit his job at the Horseshoe. He had also traded in his old car for a black Pontiac with all the extras. “I did not know how he was making his money,” Ann Roberts would tell the police later. “But he always had enough for our regular needs, and always had an automobile.” Soon after, Jackson traded in the Pontiac for a metallic-blue 1949 Oldsmobile Rocket, which he proudly drove over to his old workplace. Now he was the big tipper with the flashy car and the wad of cash. He was doing so well that Ann was able to quit modelling. On July 2, 1951, they moved again, this time to a cottage at Musselman Lake, northeast of
Toronto.
Eight days later, four gunmen hit the Woodbridge Royal Bank for the second time in two months, this time taking $10,000. The Telegram called it a “return engagement.” The robbers would have taken a lot more, but even with a gun at his head, bank manager Glen Newans refused to open the vault. Soon after the robbery the police found the getaway car abandoned on a country road outside Woodbridge. A farmer told the police that two young blonde women had been parked for some time in the same location where the getaway car was found later. Descriptions of the women and the car were broadcast to police forces across the province, and that night the headlines told the story.
Three days after the Woodbridge robbery, four Thompson sub-machine-guns and several revolvers were stolen from the army base at Camp Borden, along with a large quantity of ammunition.
On the afternoon of July 24, a green 1951 Buick driven by Valent “Val” Lesso pulled up at the Musselman Lake cottage. Lesso was six years younger than Lennie, who introduced him to Ann and told her they were good friends. The two men spent much of the three hours Lesso was at the cottage huddled in private conversation.
Two days later, on a sultry afternoon in the Holland Marsh farming village of Bradford, thirty miles north of Toronto, off-duty OPP constable Reg Wilson noticed a suspicious man near a late-model black Ford in front of the Bank of Commerce on the main street. Wilson lived in the apartment above the bank. Without attracting attention, he walked to the side of the building and quickly up the outside stairway to his apartment. While he was loading his service revolver, three robbers, one of them carrying a tommy gun, left the bank with $4,200. The robber with the tommy gun threw it into the back seat as Wilson appeared at the corner of the building and opened fire, hitting the car four times, and perhaps, he thought, one of the gunmen. The robbers replied with a hail of bullets from inside the car. Wilson dropped to the pavement when one the shots smashed into the wall a few inches from his chest.
“If he [Wilson] had fired any sooner, he might have been cut down by the machine-gun,” said Harry Barron, who had witnessed the shoot-out from his hardware store across the street. The car, which had been stolen in Toronto earlier that day, was found abandoned on a side road four miles away. A small army of policemen set up roadblocks and searched fruitlessly for the gunmen. That night and the next day there were more sensational headlines in the newspapers.
Within an hour of the robbery, Lennie Jackson and Ann Roberts had packed their bags and checked out of the Musselman Lake cottage. Taking a circuitous route, they drove north along the eastern shore of Lake Simcoe and rented a cottage at Paradise Camp, near Orillia. Three days later, leaving Ann at the cottage, Lennie returned to Toronto, where he had rented a room on the top floor of a three-storey rooming house on Roncesvalles Avenue.
There is no doubt that Lennie Jackson and Frank Watson had underworld connections, but Eddie Tong had his own contacts there. Jackson and Watson had become part of what police were calling the Numbers Mob, a loosely knit outfit that used walkie-talkies and numerical codes to signal each other, as if they were football quarterbacks calling plays at the scrimmage line. Tong had been working the case since January 22, 1951, when thieves held up the Dominion Bank at Dovercourt Road and Davenport. Through his network of informers and other leads, he arrested Louis Stavroff and Tony Brunet in a Queen Street West cocktail lounge within three hours of the robbery. In Stavroff’s home, police found nine revolvers, five hundred rounds of ammunition, and enough dynamite “to blow up a city block.” Stavroff and Brunet were sentenced to fifteen years at Kingston.
The robberies continued, but so did Tong, who was pressing his informants and watching to see who was driving the new cars and flashing the cash rolls. He showed up at Musselman Lake the day after Lennie Jackson and Ann Roberts moved on. On July 28, two days after the robbery, he picked up two more suspects on Jarvis Street. In their rooming house the police found plans of the Bradford Bank of Commerce and a detailed map of the area.
Acting on a tip two days later, Tong, Jack Gillespie, and two OPP officers raided Jackson’s rooming house on Roncesvalles Avenue. They went to his third-floor room, but there was no sign of him. Disappointed, Gillespie left by the front while Tong went out the back … and came face to face with Jackson, who was climbing the fire escape to his room. “Eddie grabbed him and there was a fight,” recalled Gillespie. “Lennie could really handle himself, but he met his match with Eddie Tong.” Jackson’s forehead hit the fire escape railing, which opened a gash over his left eye where he already had a scar, but he was able to struggle free and run down a back lane, with Tong in pursuit. As they ran, Tong saw Jackson flip a small paper-wrapped bundle through the open window of a car parked in the lane. Tong gradually gained on Jackson and stopped him with a flying tackle as he reached Boustead Avenue. That night the Telegram’s page 1 headline incorrectly reported that police had fired five shots at Jackson as he was fleeing.
The bundle in the car in the lane contained $1,500 in cash, and if Tong hadn’t noticed it the police might never have recovered it, since the owner of the car had been planning to drive to Kapuskasing that afternoon. While Jackson was being arrested by Tong and Gillespie, a second police team was capturing Frank Watson at gunpoint in a downtown rooming house.
Tong and Gillespie took Jackson to the third-floor detectives’ office at College Street, where he was held on vagrancy charges, pending a line-up the next night. The evening after their arrests, Jackson and Watson were placed in what would be described as the largest line-up procedure in Toronto police history, with more than fifty bank employees, customers, and other witnesses studying ten men in the lineup room over a three-hour period. Afterwards,
Jackson and thirty-five-year-old Watson were each charged with robbing five banks.
Ann Roberts was worried. She hadn’t heard from Jackson since he left the Orillia cottage in his Oldsmobile early on the morning of July 29. She learned of his arrest on a radio news broadcast the next day. He was being held without bail. Ann returned to Toronto and stayed with Jackson’s sister, Mary. Tong arranged for Ann to see Jackson at police headquarters, and after that she visited him twice a week at the Don Jail. In a statement to police six months later, Ann said that up until the time of his arrest for the Bradford bank robbery, “I had never seen him with a gun, had never heard him talk about guns, and had never seen him with a large sum of money. From the time I met Leonard until the time he was arrested we did not associate with anyone. When we went out, we went out together. We did not have any visitors come to our home, and we did not receive any phone calls, although there was a phone in the house.”
On August 21, 1951, Jackson was taken to the Barrie courthouse for a preliminary hearing on the Bradford robbery. He was ordered to stand trial. On the courthouse steps he saw Tong and Gillespie. “Lennie and Watson were coming out of the court in handcuffs,” recalled Gillespie, “and Lennie looked at Tong and said something to him like, ‘You better watch out – you’re going to get it.’ I don’t know if that was it exactly, but I know it was sort of a threat. Eddie was used to that, he just smiled. Lennie never liked Eddie Tong. I don’t think he could accept that he met his match with Eddie.”
Lennie Jackson had been in the Don Jail for two and a half months when Edwin Alonzo Boyd arrived in mid-October and was assigned a cell next to his. Boyd was eight years older than Jackson, but they had more in common than they realized.
On October 25, 1951, eight days after Boyd’s arrival in the northwest No. 3 Corridor, William R. “Willie” Jackson – no relation to Lennie Jackson – was assigned a cell near the other two. Willie Jackson was awaiting removal to Kingston, pending appeal of a seven-year sentence for robbery with violence. Willie was five-foot-seven and had receding curly dark hair, blue eyes, and the name “Eleanor” tattooed on his right forearm. He had grown up streetwise in Toronto’s tough Cabbagetown neighbourhood and had skipped school so often that Children’s Aid was monitoring him by age twelve. By thirteen, he was in reform sc
hool for stealing; at sixteen, he had run off to Montreal, where he was charged with vagrancy. By eighteen, he had graduated to car theft, and when he broke the terms of his two-year probationary sentence, he was sent to the Guelph Reformatory for ninety days.
Willie, who was then twenty-five, liked to tell jokes, and later on, when he became known as a member of the Boyd Gang, he would mug for the cameras and toss one-liners to reporters. The newspapers would nickname him “the Clown”, although by the time he met Ed Boyd and Lennie Jackson in the cells at the Don Jail, there was nothing in his criminal background to laugh at.
From car theft he had graduated to robbery – usually with violence. Willie Jackson was a mugger. In the summer of 1948, after serving two years in the Manitoba Penitentiary, he returned to Toronto. He needed money to maintain the drinking habit he had developed, and he knew only one way to get it. In Allan Gardens on June 5, he robbed Turpo Coté of his wallet containing $7. Two weeks later he assaulted Russell Hardy and robbed him of a small amount of cash. And two days after that he approached Montreal businessman Gilbert Holmes, who was sitting on a bench at Queen’s Park just after 11 p.m.
“Do you have a match?” asked Willie. Holmes gave him a match, and Willie sat beside him, striking up a conversation. Two of Willie’s accomplices suddenly appeared behind them. One of them thrust a nickel-plated revolver into Holmes’ back and ordered him into the bushes, where they took his wallet and wristwatch and the key to his Bay Street hotel room. The wallet contained $6.75. The trio then forced Holmes to accompany them along Bloor Street to Sherbourne, where they took him into the ravine below the bridge and tied him up. Willie laughed and held up the key.
“You guys watch him,” he ordered. “I’m going to see what I can pick up in his hotel room.”
