By now Sir Barton had acquired an amusing swagger; his sore feel caused him to walk pigeon-toed. He had become nearly impossible to train, choosing to extend himself only in races. Bedwell tried to trick the colt into training by lining up other horses to run with him and make him think he was in a race. "To get him fit, you have to half-kill him with work—and a lot of other horses as well," Bedwell told Bert E. Collyer of the Chicago Evening Post.
By the end of 1919 Sir Barton had won eight of 13 races and was chosen Horse of the Year by the thoroughbred racing associations. Ross considered retiring his champion rather than subjecting him to the rigorous handicap schedule of 1920. But Bedwell convinced him that Sir Barton could handle the heavier schedule despite his physical problems.
Sir Barton had a lackluster spring but by late summer was among the leaders of the handicap division. By fall it was clear that only one colt could keep Sir Barton from repeating as Horse of the Year.
Man o' War had been defeated only once, as a 2-year-old in the Sanford Memorial, by a colt with the appropriate name of Upset. As a 3-year-old Man o' War won all 11 of his races, including the Preakness, the Withers, the Belmont, the Dwyer, the Potomac Handicap and the Jockey Club Gold Cup. (Man o' War was not entered in the 1920 Kentucky Derby; his owner, Samuel D. Riddle, thought the 1�-mile race would be too taxing for a 3-year-old so early in the year.) It seemed only fitting that Man o' War and Sir Barton should meet to decide the Horse of the Year title. Riddle and Ross decided to run their champions in a match race at Kenilworth Park in Ontario on Oct. 12.
The Kenilworth Gold Cup, with a purse of $75,000 and a distance of 1� miles, was dubbed the Race of the Century by noted turf writer Joe Palmer. Man o' War was made the 5-100 favorite. "Man o' War will not so much run with Sir Barton as hurdle him," Palmer wrote. The two jockeys—Frank Keogh on Sir Barton and Clarence Kummer on Man o' War—were both told, Get up front and stay there.
When the flag dropped (the starting gate had yet to be invented; the horses simply lined up behind a ribbon), Sir Barton, on the rail, got the first jump. His lead was temporary. The only film ever taken of Sir Barton tells the story: Man o' War, with his long, effortless stride, kicked dust into Sir Barton's face, leaving the Triple Crown winner far behind in the stretch. Despite a broken stirrup, Man o' War won by seven lengths in a track-record 2:03. Sir Barton hobbled over the finish line, having lost all four shoes.
After the race many writers blasted Ross for running a horse with bad feet against the newly anointed Horse of the Century. Sir Barton never won another race and was retired to stud in Virginia, where he stood for 11 years. In 1933 he was turned over to the military in Nebraska, where his stud fee was reported to have been between $5 and $10. Later that year he was bought by Dr. J.R. Hylton of Douglas, Wyo., who retired the old champion to his ranch. Sir Barton died on Oct. 30, 1937, and was buried near his paddock.
In 1968, through a Jaycee-sponsored effort, Sir Barton was exhumed and his remains placed beneath a statue in Washington Park near Douglas. Alas, Sir Barton suffered one final indignity. The fiberglass statue that marks his grave is not a likeness of the first Triple Crown champion. It is a generic horse made by a Montana company that specializes in life-sized models of large animals.