John Kenneth Levison Ross, commander of a Canadian destroyer in World War I, bought the colt from Kentucky breeder John E. Madden in the spring of 1919 for $10,000 and entered him in the Kentucky Derby to set a quick pace and burn off the field for his beloved Billy Kelly. Instead, Sir Barton led wire to wire to become the first maiden to win the race.

It was a preposterous feat for a colt who was 0-for-6 as a 2-year-old and made his seasonal debut in the Derby. He duplicated the Derby victory four days later in the Preakness, made a detour off the not-yet-Triple Crown trail to win the Withers Stakes, then bested a three-horse field to win the Belmont.

Sir Barton's connections never got to celebrate a Triple Crown. As the first to accomplish the feat, Sir Barton was in unfamiliar and unexpected territory, and the series was not known as the Triple Crown until decades later.

The cantankerous Sir Barton struggled with health his whole career, and his connections chose to race him despite his pain. His feet were so tender that piano felt often was placed under his shoes. Still, he threw them during races, once losing four.

Sir Barton's Kentucky Derby win was the second for Madden, who co-leads breeders with nine Derby wins and is the only person to breed, own and train a Derby winner.

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