Man O’War vs Sir Barton

On Tuesday, October 12th, 1920 a horserace between Man O’War and Sir Barton, the two best racehorses of the day, was held at Kenilworth Park Racetrack in Windsor. Attended by a crowd estimated at 30,000, the contest was one of the most famous horseraces of the twentieth century.

During the summer of 1920, news of a potential matchup between Sir Barton, the first

Man O'War vs Sir Barton

Man O’War vs Sir Barton,
Border Cities Star, October 13, 1920, page 10

ever winner of the American Triple Crown the year before, and Man O’War, a horse who had only lost once in twenty one races, began to circulate. Abe Orpen, owner and operator of Kenilworth Park Racetrack (located on what was then the southern outskirts of the city on Howard Avenue, opposite the present-day Devonshire Mall), outbid several competitors and secured the rights to hold the event. The winner would receive $75,000, the most prize money awarded for a horserace in history up to that time, and a gold cup valued at $5000.

In the morning on the day of the race, dozens of specially-designated trains brought thousands of spectators to the scene. Some of the many illustrious people among the crowd that day were Thomas Shaughnessy, former President of the Canadian Pacific Railway, August Belmont Jr., the man who financed the construction of New York’s subway system, and World Heavyweight Champion Jack Dempsey. It was estimated that $220,000 in bets, the equivalent of 2.7 million dollars in 2020, were placed that day. In the end, the race was not even close. After racing neck and neck for a short distance, Man O’War pulled ahead and won by seven lengths. The contest holds the distinction of being the first horserace in history to be filmed in its entirety.


“Orpen Secures Big Race for Windsor Track,” Border Cities Star, September 25, page 13

“Two Monarchs of the Turf Ready for Wonder Race,” Border Cities Star, October 11, 1920, page 1

“Sir Barton No Match for Riddle Horse Who Didn’t Even Work Hard,” Border Cities Star, October 13, page 1

Canadian Horse Racing Hall of Fame, A.M Orpen profile page

Youtube, Footage of the Race

Youtube, Footage of the Race

Man O’War vs Sir Barton

Man O’War vs Sir Barton, Border Cities Star, October 9, 1920, page 15