Sir Barton was foaled in 1916, the son of Star Shoot out of Lady Sterling. He was born long before the title "Triple Crown" was given to the three races, and therefore never received any glory for the task.
At the 2 year old sales in Saratoga in 1918, Sir Barton was purchased for $10,000 by a man named Commander JKL Ross, of Maryland. Ross entered Sir Barton in the Derby as part of an entry with his much more respected colt, Billy Kelly. But it was Barton, with jockey Johnny Loftus, who pulled the lead and led from wire to wire, winning by five lengths over his stablemate. He was then shipped immediately to Pimlico to run the Preakness, only 4 days after the Derby. He took the lead again and stayed there until the finish. At one point in the stretch he was in the lead by six lengths but was pulled up and won by four lengths in a canter. Ten days after the Preakness he was entered into the Withers Stakes and took first place there too. From there he was entered into the Belmont and became the first Triple Crown winner.
Several months after winning the Triple Crown, Man-O-War entered the racing scene.
As a 4 year old, Sir Barton won five of twelve starts, but finished off the board twice. His chronically sore feet and ugly temperament began to get the better of him.
With both Sir Barton and Man-O-War having impressive records, the call soon came for a match race. On October 12, 1920, an hour before the race, Barton's jockey, Earle Sande, was so unnerved by the event that he was replaced by Frank Keogh.Sir Barton's feet were bothering him and Man-O-War won the 1 1/4 mile race by seven lengths in track record time.
Sir Barton retired in 1920 and was only moderately successful at stud. Later he served his country as a U.S. remount stallion. He died October 30, 1937 at the age of 21, and was buried by his owner Dr. J.R. Hylton on his ranch on the Laramie mountain foothills. Later his remains were moved to Washington Park in Douglas, Wyoming, to honor America's first Triple Crown Winner.
Sir Barton was voted to place number 49 of the top 100 racehorses of the 20th Century, while Man- O-War placed number 1.