Every racing fan has that one story about the time they nearly backed a massive longshot but chickened out at the last second. We’ve all been there: staring at the odds board, seeing some outsider at 50-1 or higher, and thinking “what if?” The truth is, some of the most incredible moments in racing history came from horses nobody gave a prayer.
Most punters play it safe when they head to the track. Smart money often goes toward combination bets that cover multiple outcomes, such as lucky 15 tips for today that split four selections into 15 separate wagers: four singles, six doubles, four trebles, and one accumulator. This approach gives you several ways to win something back, even when your main picks don’t fire. But the stories that get told decades later come from the crazy punts that somehow paid off against all logic.
Take Donerail back in 1913. This three-year-old went to post at 91-1 for the Kentucky Derby, and those odds looked generous. Owner Thomas Hayes didn’t want to run him against such tough competition. His jockey, Roscoe Goose, had to talk him into it, promising they’d at least grab some place money. Hayes gave his final instructions: just try to finish in the money. What happened next changed racing forever. Donerail found another gear down the stretch and won going away. That $2 ticket paid $184.90, and more than 110 years later, no Kentucky Derby winner has gone off at longer odds.
Jim Dandy pulled off something even more ridiculous at the 1930 Travers Stakes. Triple Crown champion Gallant Fox looked unbeatable that day at Saratoga, but Jim Dandy had different plans. This horse was such an afterthought that he went off at 100-1; bookmakers practically gave away the tickets. Heavy rain turned the track into soup, which suited Jim Dandy perfectly. The favourites got into a speed duel and went wide around the turn, leaving the rail open for Jim Dandy to sneak through and win by six lengths.
Then there’s Arcangues at the 1993 Breeders’ Cup Classic. American racing fans had never heard of this French horse, even though he’d won big races across the pond. His European victories had all come on grass surfaces, and this was dirt. Jerry Bailey got the call to ride him, but couldn’t understand a word the French trainer said before the race. At 133-1, Arcangues was basically a throwaway bet. None of that mattered when he unleashed a devastating finish to catch Bertrando and score the biggest upset in Breeders’ Cup history.
Mine That Bird delivered another stunning upset at the 2009 Kentucky Derby at 50-1 odds. Calvin Borel worked his signature rail magic, keeping the horse tight to the inside throughout. The gelding exploded past the field in the final furlong. Rich Strike added another chapter in 2022 at 80-1 odds after getting into the race when another horse scratched.
These legendary upsets remind us that racing never stops surprising. With around 440 professional jockeys competing in Britain today, the sport creates endless possibilities for magic.