The Legendary Horseshoe Tavern. David McPherson

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The Legendary Horseshoe Tavern - David McPherson

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a really hard time getting the name ‘Horseshoe’ patented because of the similarity to Billy Rose’s famed Diamond Horseshoe nightclub in New York City … there was some sort of infringement rights; eventually, he got it. Where he got that name from, I honestly don’t know, because my dad never went to the races and he wasn’t a gambler. Maybe he just thought it would be lucky.”

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      A postcard of the Horseshoe Tavern depicting what it looked like, circa the early 1950s.

      Luck certainly played a part in Starr’s early success. On December 9, 1947, the Horseshoe Tavern officially opened. In the December 12, 1947, edition of the Toronto Daily Star, an ad for the newly opened establishment called it Toronto’s “Finest Eating Place” and proclaimed, “It’s the Rave of Toronto! You and your friends are cordially invited to the newly opened Horseshoe Tavern, where the delicious food and distinctive atmosphere is second to none.… Sunday dinner served from 2 to 8 p.m.”

      Starr’s idea was to run a tavern for the city’s workers and “outsiders,” those not part of the social elite — the blue-collar toilers in the garment and textile factories, the cops who kept the streets safe, other downtown denizens and not-so ne’er-do-well characters, wayfarers who roamed the city streets. The tavern’s first licence had a legal capacity of eighty-seven seats. In those early days, the bar’s focus was on value: good food, cold beer, and liquor. Another first, according to Time magazine: the Horseshoe was the first bar in Canada to have a television. This happened in 1949.

      Starr expanded the space over the years, buying the property next door and enlarging the Horseshoe until it eventually sat five hundred patrons. Soon, live music would rain from the rafters seven nights a week.

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      Horseshoe stationery.

      * * *

      While he stood only about five foot four, Jack Starr had a big heart and knew a few things about running a business. In a famed picture taken years later with one of his favourite Nashville performers, Little Jimmy Dickens, Starr looks like a giant next to the diminutive four foot eleven rhinestone cowboy. Like his personality, the shows Starr booked and promoted were always larger than life. The room had a barn-like vibe then, and even though it’s half the size today, it still feels like a rural retreat.

      There’s no sensible reason why a tavern that hosted country music ended up on this stretch of street. Despite this anomaly, Toronto music lovers around the world are thankful. What did Starr know about running a bar? Not much, but he knew how to run a successful business. And, he was also driven — possessing a work ethic inherited from his father. During the years he ran the bar, he rarely left. He was a fixture at the door; after the doorman, he was usually the next person who greeted you upon entering the building. Before shows and during intermissions, he’d walk from table to table saying hello to the regular patrons, making sure his adopted family always enjoyed themselves.

      Starr left a lasting impression on all the artists who played within those four walls, as well as with all the men and women who drank a cold beer on a stool in the front bar or stopped in for a late-afternoon game of pool. Starr was fair. Everyone respected him. Natalie Clairman recalls, “People loved him. He quickly became a fixture on Queen Street. All the policemen knew him, including all the undercover cops. They never paid for a drink in his bar.

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      A view of the cityscape near Queen and Spadina in the mid-1920s near the intersection where Jack Starr would later open the Horseshoe Tavern.

      Every Christmas, he would host a big party at the Horseshoe for the police. All the people from the schmatta business also knew him too … he was very friendly and very outgoing.”

      Starr was also a regular at neighbourhood restaurants like Lichee Garden, which opened in 1948 and boasted an enormous dining room with a capa­city to serve as many as 1,500 customers a day. Provincial and federal political leaders and other celebrities often dined there. Lichee Garden even had a band and offered dining and dancing until closing at 5:00 a.m. Whenever Starr showed up, a murmur of excited chatter would go through the place; everybody knew his name and loved to see him. Clairman remembers a dad she rarely saw during those early days when he was running and expanding the business: “It was a night business. He would go into the club after dinner, stay until it closed, and be there early the next morning to tally up the bar sales from the previous night and do inventory.”

      An avid and accomplished golfer, Starr took rare breaks from running his beloved tavern in the summers to tee it up at Oakdale Golf and Country Club, near Downsview, where he was a member. A newspaper report from 1954 mentions Starr winning the annual Toronto Hotel Association Championship. Following his round, the businessman sometimes took an afternoon siesta before heading back to the bar. Some of Gary Clairman’s earliest memories, as a nine-year-old, are of going down to the bar on a Sunday afternoon, eating a banquet burger with fries, and just hanging out with his grandpa. He recalls:

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      (Top and bottom) Looking eastward on Queen Street to Spadina Avenue on October 12, 1933, fourteen years before Jack Starr opened the Horseshoe Tavern at 368–370 Queen Street West.

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      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

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