LITMIR.BIZ

      Sometimes, if I slept over at my grandparents’ house, Jack would get up and we would go down to the Horseshoe together before it opened. There was a trapdoor behind the bar where he kept the safe. That room is still there. He would open the safe, and it would be full of one-dollar bills because everything from a beer to a shot of liquor cost one dollar in those days. There would be stacks and stacks and stacks of ones. I would help him count them. Then, we would put them in bundles of twenty-five or fifty to take to the bank.

      In later years, these family moments at the Horseshoe Tavern continued. As Pa was then in his nineties, living alone in an apartment, Starr would pick up his dad at 8:00 a.m. and take him down to the bar. While Starr tallied up the receipts and took inventory from the previous night’s sales, his dad kept busy. Natalie Clairman recalls, “My grandfather would take a shot glass, go around the bar and pour the rye, Scotch, and gin — the dregs of whatever was left in the glasses on all the tables into his glass — then he would sit in a chair, drink it back, and fall asleep for the rest of the morning until Jack took him home!”

      Despite the presence of lowly citizens who were regular barflies at the Horseshoe, fights were rare. Mixing with these drifters and law-abiding country and western music lovers were detectives — rough, hard-nosed characters — as well as criminals in the making who turned to the wrong side of the law to survive and make ends meet. These bookies, bootleggers, and bank robbers were the people below the veneer of the city’s stereotype of “Toronto the Good.” One of the tavern’s most famed patrons in those early years was the mastermind bank-robbing bandit Edwin Alonzo Boyd, who later escaped not once — but twice — from Toronto’s Don Jail, and other members of his notorious gang drank there as well.

      Sergeant of Detectives Edmund “Eddie” Tong’s old battered Buick was often seen parked outside one of the many newly opened taverns in downtown Toronto, including the Horseshoe, during those years. As Brian Vallée writes, “People called Tong ‘the Chinaman’ because of his name and his black hair, which he combed back off his forehead.” Tong kept an eye on the underbelly of Toronto, where the likes of Boyd and his gang dwelled. Starting in 1949, the cop routinely visited places like the Silver Rail on Yonge Street, the Holiday Tavern at Queen and Bathurst, and the Horseshoe Tavern at Queen and Spadina. Since opening and being some of the first establishments to obtain liquor licences in the province, these bars had quickly become the watering holes of choice for Toronto’s criminals and their hangers-on. Tong and his partner at the time, Jack Gillespie, would go into the bars just to let these patrons know they were around and they were watching.

      Barkeep Lennie Jackson was a drifter, a pool shark, and one of these hangers-on; he landed a job at Starr’s tavern after moving to Toronto from Niagara Falls. As Vallée writes, “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.” Jackson ended up quitting the Horseshoe and becoming a wanted man for his role in a series of bank robberies with the Boyd Gang. He was eventually shot by Gillespie, but not before he and his fellow partner in crime, Steve Suchan, shot and fatally wounded Tong in March 1952.

      While there are a couple of old newspaper stories about shootings near the Horseshoe in the 1950s, these events were rare. Asked about this by the Globe and Mail, long after he had retired and the bar was set to celebrate its fortieth anniversary, Starr, then seventy-seven, replied, “Oh, there were a few freak incidents like that. In the early days, we spent about 90 percent of the time at the door keeping out the type of people we didn’t want in. But over the years we had a cross-section of all kinds: college kids, doctors, lawyers, and businessmen.”

      Besides this eclectic cast of colourful characters, most of Starr’s regular patrons were good-time folks from the East Coast. Daughter Natalie Clairman remembers, “At a time when the economics in the Maritimes was not very good, they were migrating to Toronto. They were country music fans, so they eventually persuaded my dad to bring in some music. It sounds simple, but that’s as simple as it was.” Adds Natalie’s son, Starr’s grandson Gary Clairman, “I’m sure Jack became a fan of country music, but it’s not like he was playing it around the house. He was smart enough to know though that it was going to fill the place.”

      The country and western acts certainly helped pack the establishment. Beginning in the early 1950s and lasting until he retired in the mid-1970s, Starr’s booking

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