Marking 100th Anniversary of Historic Race in Windsor, Ontario

Canadian Horse Racing Hall of Fame

In a special online event on October 12, 2020, exactly 100 years to the day after Man o’ War and Sir Barton competed in a match race at Windsor’s Kenilworth Park, the Canadian Horse Racing Hall of Fame named Man o’ War its 2020 Legend Honouree. The announcement was the culmination of a week-long social media campaign celebrating the original “Big Red’s” monumental win, which placed an emphatic exclamation mark on his remarkable career.

What some have called “the greatest day in Canadian horse racing,” the Kenilworth Gold Cup took place in Windsor, Ontario, on October 12, 1920, when the two biggest names of the day competed in a historic match race.

The immortal Man o’ War, holder of more records than any other horse and the leading three-year-old of 1920, was owned by Samuel D. Riddle of Philadelphia. Sir Barton, the Canadian-owned champion of the older-horse division and America’s first Triple Crown winner in 1919, was owned by Commander J. K. L. Ross of Montreal. The two Thoroughbreds faced off to settle the supremacy of the North American turf.

Man o’ War in 1920.

Man o’ War was the prohibitive 1-to-20 favourite, with bettors wagering a reported $220,000 on the race organized by the track’s operator, Mr. Abe Orpen, and considered a major coup in a time Canadian racing needed a boost following the government’s wartime ban on betting in 1918 and 1919. It was a highly anticipated event that would become the first horse race filmed from wire to wire, with the footage later shown in movie theatres across the continent.

Originally proposed as a contest that might also feature a third great racehorse of the time, Exterminator, the terms of the race at a mile and a quarter and a weight-for-age format were not to the liking of Exterminator’s owners so he was not entered, resulting in a match race between Man o’ War and Sir Barton.

In front of an estimated 30,000 spectators, Sir Barton had the advantage at the start and led to the first pole by little more than a length. By the half-mile, Man o’ War had overtaken and passed Sir Barton to lead by two lengths. By the three-quarters, the lead had been cut to a length and a half. Man o’ War’s jockey responded by letting his mount out to open his lead to four lengths as they entered the stretch. With Sir Barton being urged to his limit, Man o’ War continued to run effortlessly to cross the wire ahead by seven lengths, buoyed by the cheers of the massive crowd, to lower the track record for a mile and a quarter by six and two-fifths seconds.

The two competed for a $75,000 US, winner-take-all purse with accompanying Gold Cup, designed by Tiffany & Co and valued at $5,000. That same trophy was later donated to Saratoga Race Course by Mrs. Riddle, the wife of Man o’ War’s owner, and is now known as the Man o’ War Cup, presented each year to the winner of The Travers Stakes.

Following the race, the Canadian Sportsman and Live Stock Journal carried a photo of Man o’ War on the cover of its October 18th, 1920 issue accompanied by a caption reading “MAN O’ WAR — Winner of the $75,000 race at Windsor on Tuesday, October 12th, defeating Sir Barton in a most decisive manner and showing himself to be a wonder horse.”

Man o’ War at the nursery stud with trainer Joseph Bryan Martin.

Man o’ War’s lone race on Canadian soil at Kenilworth Park was his final career start and win, something that was repeated by Exterminator and a later “Big Red,” Secretariat, who also concluded their careers with wins at Canadian tracks. Over his two-year career, Man o’War won 20 of 21 races, and set three world records, two American records, and three track records.

The recognition bestowed on Man o’ War exactly 100 years to the day after his win on Canadian soil became possible when the Directors of the Canadian Horse Racing Hall of Fame expanded eligibility to the Hall to include those who have significantly impacted Canadian racing. Since that decision, such greats as Secretariat, Dahlia, and the venerable Dan Patch have all been honoured by the Canadian Horse Racing Hall of Fame.