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Gary Clairman, as well as by all who knew him — was born in Russia; he was a member of the Russian cavalry during the Russo-Japanese War (1904–05). Supposedly, he was also the bugler in the troop. Japan won the year-long battle that forced Russia to abandon its expansionist policy in the Far East. During the short conflict, Pa, fighting at the front, was shot straight through the heart. Somehow he survived. When the war was over, he, along with the rest of his troop, was briefly arrested for desertion because there had been no communication informing their superiors the conflict had ended. His bravery, sense of adventure, and ability to survive are traits the elder Starr passed on to his son Jack, one of seven children. This dogged determination, entrepreneurial spirit, and can-do attitude served Jack well through the years, and he became an astute small business owner.

      By the time the second decade of the twentieth century arrived, Starr’s grandfather was tired of the politics, strife, and continual persecution in Eastern Europe. Like so many Polish and Russian Jews before him — and after him — he immigrated to Canada with his wife and two children to provide them with a better life. The Starrs settled on a farm in Whitby, Ontario, right where the 401 exit ramp to the Toronto suburb sits today. Jack was born in 1913 on this rural property. For years, the Starrs used the farm as a way station and inn for Jewish kosher peddlers trying to eke out a living. Later, the family moved to downtown Toronto, buying a house at 153 Manning Avenue, near Dundas and Bathurst.

      To mark the Sabbath many Jews did not work on Saturdays, making it difficult for some of these immigrants to get factory jobs. Instead, these new Canadians often started their own businesses and hired their friends and family to work for them. During the early to mid-twentieth century, the garment industry exploded in downtown Toronto and other North American cities, like New York. For a period, the clothing industry was one of the biggest employers in the United States, producing 95 percent of the country’s garments. A similar trend occurred north of the border. Early on, the industry in Canada employed mainly Italians and Eastern European Jews, who called it the schmatta business (Yiddish for “rags”).

      Starr was one of the early entrepreneurs who found success in this line of work. In his early twenties, the hard-working first-generation Canadian started in the garment manufacturing business, first learning the trade working as a cutter in a women’s wear factory. Before he owned a store of his own, he and his brothers owned a manufacturing company called Hollywood Shirt. Located downtown in what was then referred to as “Schmatta Alley,” the clothing manufacturer made shirts and other clothes and did a large amount of business through the Sears catalogue. Jack later sold his share of the business to two of his siblings and struck out on his own to begin his next venture: Hollywood Skirt.

      Postwar Toronto in the late 1940s and early 1950s was considered a bastion of provincial conservatism, but as more immigrants arrived, and more liquor licences were granted, this perception changed. Toronto evolved into a progressive, cosmopolitan centre of commerce and industry. Queen Street West in the fifties was a working-class neighbourhood inhabited mainly by Italians and Jews.

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      A Toronto garment workshop, circa 1920s, shows Jewish workers operating sewing machines.

      Flash back to 1947. Starr — quiet, congenial, and soft-spoken — surprised his family by purchasing the building at 368–370 Queen Street West from Warren Drug Co. Ltd., with a plan to open a restaurant and bar.

      Prior to becoming the Horseshoe Tavern we all know and love, this property, at the edge of Toronto’s garment district, changed hands constantly. The building first housed a blacksmith in 1861; later, it shared the space with an engineer and a pair of butchers. Over time, machinists, greengrocers, and many other commercial businesses — from clothing and footwear retailers to the aforementioned drugstore — called the address home. Nothing ever really stuck for long until Starr arrived with his vision.

      While it’s a coincidence that a stable once resided in the space of Starr’s tavern, it’s appropriate — in the ensuing years the Horseshoe became home to some of the top acts from Nashville and the stomping grounds for future members of the Grand Ole Opry. Since the property also once housed a blacksmith’s shop, it’s possible that’s where Starr came up with the name. Or, perhaps he was not aware of this historical fact and the name came about simply because he sensed the property, like a horseshoe, was lucky. What is known is that Starr was dabbling in real estate at the time, and the purchase surprised his family. Daughter Natalie Clairman, née Starr, recalls having just come home from summer camp when her father shared the news that he was leaving the ladies’ wear manufacturing business: “Honestly, I don’t know what put that bee in his bonnet. I think he just got tired of doing that and somehow he got it into his head to open a restaurant.”

      Over the course of months of sweat and hard labour, Starr invested about $150,000 into the business and built the tavern from the ground up. First, he gutted the building, knocking down the clapboard stores that then occupied the site. Then, he put in a kitchen, a bar, and seating for close to one hundred patrons. At the time, the new, loosened provincial liquor licence laws (circa 1947) permitted Starr to convert the commercial property to an “eatery-tavern” and start serving alcohol. Naturally, he started the process to obtain one of the city’s first liquor licences. This took time and caused Starr some stress. Dealing with government bureaucracy was no different in Starr’s time than it is today. Forms needed to be filled out, criteria met, and papers signed, and then one had to wait for approval from the Liquor Licensing Board of Ontario (LLBO).

      Some of the biggest opponents to bars such as Starr’s obtaining the right to sell liquor either with or without meals were clergy. Reverend J. Lavell Smith of the Church of All Nations, up the street from the Horseshoe Tavern at 423 Queen Street West, denounced the granting of licences to all restaurants in the vicinity of his church. “There are enough drunks on Queen Street as it is, and there is [no] need for more outlets,” he told the liquor board. “We had two drunks barge in to our service the other night.”

      Did Starr bribe someone with a bag of cash to get the paperwork approved and to expedite the government’s stamp of approval? There’s no one left alive to confirm whether this rumour is true. No matter, eventually Starr succeeded — securing the second Ontario licence granted by the newly created LLBO, shortly after the Silver Rail on Yonge Street, which opened earlier that year on April 2.

      When Starr tried to patent and register the tavern’s name, he ran into another stumbling block. As Natalie Clairman recalls, “He initially had 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

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