Abram Michael (A.M. or Abe) Orpen started his working life as an apprentice to a carpenter, a career path his mother set him on, but a near-death experience prompted the young Orpen to set his sights on a different path. He walked away from carpentry and into entrepreneurship, starting his own brickworks and lumber business, and then buying the Alhambra Hotel, a popular gambling saloon, in Toronto. There, he learned how bookmakers worked and, through hard work and innovation, he survived the transition from bookmakers to pari-mutuel betting, understanding that the money to be made now came from owning the tracks. He used the knowledge gained in running the Alhambra into his ownership of first Dufferin Park in Toronto and then Kenilworth Park in Windsor, Ontario.

Orpen’s Kenilworth was not the first racetrack of that name. The original had its short-lived run in Buffalo, NY, done in by the Hart-Agnew laws after only six years of racing. While the land was redeveloped into a residential area, Orpen and his partners bought the steel grandstand of the original Kenilworth and then had it dismantled, shipped, and rebuilt in Windsor. In September 1916, Windsor went from one racetrack to three, with both Devonshire Park and Kenilworth Park joining the Windsor Jockey Club. Located just across the border from Detroit, Windsor was an ideal spot for both Canadians and Americans to watch and wager on the horses that shipped there. Orpen’s operations were democratic in nature; blacks worked alongside whites and his grandstands didn’t have jockey clubs and owners’ boxes.

The blue collar nature of Kenilworth might not have attracted the Eastern elite of racing right away, but it did attract a name of some import to Sir Barton’s story — H.G. Bedwell. Before he went to work for Commander Ross, owner/trainer Bedwell brought his string to Kenilworth for the track’s inaugural meet in September 1916, winning three races on the meet’s second day. Despite the modest purses of $600 – $800, Kenilworth’s first two meetings in September and October had plenty of horses and enough attendance to show that the new track had potential to grow.

Orpen never stopped going for bigger and better for his tracks, always looking for chances to grow and innovate. A bare four years after opening Kenilworth, Orpen battled Colonel Matt Winn, the titanic promoter who helped make the Kentucky Derby an event, for the elusive match race that all of horse racing wanted: Man o’ War v. Sir Barton v. Exterminator. Orpen took the lead, offering more and more money, barely giving Winn the time to put in a competing bid before upping the ante again. In mid-September 1920, negotiations in New York made it clear that the race was going to be Man o’ War v. Sir Barton; Kilmer refused to concede the issues of distance and weight and thus Orpen moved on without the great Exterminator. Orpen even traveled all the way from Toronto to Havre de Grace to seal the deal with Commander Ross and Samuel Riddle for a $75,000 (+ $5,000 gold cup) winner-take-all Kenilworth Gold Cup, the match race between Sir Barton and Man o’ War. Colonel Winn’s offer of the same was too little, too late despite assurances that he too had the ears of Ross and Riddle.

After Man o’ War dominated Sir Barton in the Kenilworth Gold Cup, Kenilworth and other Toronto-area tracks continued to operate until the early 1930s. As the Great Depression took its toll worldwide, people had less and less pocket money to gamble with. Kenilworth held its last meet of note in 1935; by 1937, with a new racetrack open in Detroit, Kenilworth was no longer a part of the racing scene in southern Canada. Orpen died in September 1937, leaving his holdings to his son Fred. Eventually, Devonshire and Kenilworth were both torn down to make way for residential developments. Dufferin closed in 1955, destined to follow its compatriot tracks in becoming homes for the growing population in the Toronto area. Interestingly, a wading pool in Dufferin Grove Park, near the former Dufferin Park racetrack, had a pool named for A.M. Orpen donated by his son Fred in 1954.

Eight decades after its closing, Kenilworth Park is just a memory now, but it lives on in the history of horse racing as the spot where Sir Barton challenged Man o’ War in the “Race of the Century” on October 12, 1920. Ninety-eight years later, that autumn day at Kenilworth lives on in sepia-tinted photographs and snippets of black-and-white moving images, their sights and sounds preserved in words on pages like those you will find in Sir Barton and the Making of the Triple Crown, coming May 2019 from the University Press of Kentucky.