Jim Dandy might be the racehorse most famous for losing. The story isn’t heartwarming enough for a folksy biopic or a Laura Hillenbrand book, but his out-of-nowhere victory at the 1930 Travers Stakes is nonetheless cemented in American equestrian lore. At the historic Saratoga Race Course—where the Travers is still held—legend has it that bookies offered odds as long as 500–1 and went bust in the upset. The horse was allegedly born with “eggshell hooves,” painful to run on in most conditions, yet on that fateful, muddy afternoon, Jim Dandy had the cushion he needed to secure the win. The two favorites going into the Stakes, Gallant Fox (1–2) and Whichone (8–5), went on to have fruitful, lucrative racing careers. Jim Dandy would not. He “retired”—whatever that looked like for a losing racehorse during the Great Depression—nine years later, at age twelve. Out of 141 career starts, he won seven. Yet it’s because of his historic losing streak that Jim Dandy became a patron saint to track bums (an affectionate title, I promise) in Saratoga and beyond. Proof, even if it’s nearly a century old, that even the biggest loser could be just one race away from a jackpot.
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