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Man o' War raced ten times as a two-year-old and, after a spectacular first win at Belmont, was entered by his owner Sam Riddle only in stakes races. He quickly established himself as the best two-year-old around, winning the Keene Memorial Stakes by three lengths and then taking the Youthful Stakes and the Hudson Stakes. By then he was carrying 130 pounds, including his jockey, saddle, and extra ballast added to slow him and give other horses a more equal chance, but the weight penalty made little difference as he easily won the Tremont Stakes and the United States Hotel Stakes, and also won an unofficial match race against Golden Broom. In the Sanford Memorial Stakes, the only race he ever lost, he likely got off to a straggling start and then became boxed in at the rail, allowing Upset to win by half a length. Man o' War later beat Upset in six other races, one of them before the Sanford, and ten days after that loss he defeated Upset by a length in the Grand Union Hotel Stakes. He then won the Hopeful Stakes and the Futurity at Belmont Park, becoming an object of adulation among racing fans and earning the label “sensational” from sportswriters, though the full measure of his greatness was not seen until the next season, when as a three-year-old he swept all before him.
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Lexington-Fayette, Kentucky · United States