Were Upset not part of the foal crop of 1917, it is entirely possible that he would be far more than a footnote in racing history. Instead, he is mostly forgotten other than for the false notion that his name is the inspiration for the word describing an unlikely event [1], most often used in the context of sports.
In reality, the term “upset” had been in use for 50 years before the horse Upset became the first and only horse ever to defeat Man o’ War, thought by many racing experts as the greatest of all time.
Upset was no slouch. He was a well-bred son of the top sire and racehorse Whisk Broom, owned by the powerful stable of Harry Payne Whitney, and trained by James Rowe Sr., one of the great horsemen in racing history. Rowe had trained Whitney’s filly Regret to win the Kentucky Derby in 1915 and saddled a record eight Belmont Stakes winners.
Coming into the 1919 Sanford Memorial Stakes for 2-year-olds at Saratoga, Man o’ War was considered the best of his class, having won his first six starts. He was the 1-2 favorite, but Upset was far from dismissed as the third choice in the seven-horse field. He had been a solid second to Man o’ War in their previous encounter in the U.S. Hotel Stakes, also at Saratoga.
But in the Sanford, a poor beginning by Man o’ War, attributed to an error by the substitute starter, enabled Upset to get away to a clear lead that Man o’ War was unable to vanquish. The big red colt came up a half-length short at the wire.
Upset would test Man o’ War on three more occasions in his career, finishing second each time by respectable margins. The truth was, however, that in all of Upset’s losses to Man o’ War, the winner was much the best, often ceding large amounts of weight and almost always finishing in a canter.
Still, when Upset was out of Man o’ War’s orbit, he was a formidable racehorse. In the 1920 Derby, which Man o’ War had skipped, Upset was narrowly beaten by Paul Jones after a stretch-long duel. In all, Upset won 5 of 17 starts, with another seven runner-up efforts, four of them against the immortal Man o’ War.
