What Horse Racing Upset Was the Most Surprising?

In the intense and sometimes dangerous sport of horse racing, jockeys have occasionally died during races after falling from a speeding thoroughbred. Likewise, racehorses have been known to have heart attacks and die in the midst of a race. Frank Hayes, though, is the only known jockey to have died during a horse race, and still go on to finish in first place.

Hayes apparently suffered a heart attack while riding Sweet Kiss during a two-mile (3.2 km), 12-jump steeplechase race at New York's Belmont Park in 1923. Despite the death of her rider during the race, the horse went on to clear the last fence and cross the finish line in front of her rivals, with Hayes still in the saddle.

Win, place, and ... oh, no:

• Washington Post sportswriting legend Shirley Povich reported that Hayes appeared to be hand-riding his mount in the final furlongs, slumped over the horse’s neck. The jockey toppled from the saddle soon after crossing the finish line.
• The New York Times reported that Hayes was an apprentice jockey. “The attack probably [was] brought on by severe training to make weight and the subsequent excitement of riding his first winner,” the newspaper surmised. Hayes was buried in his racing silks three days later.
• Sweet Kiss -- allegedly nicknamed "Sweet Kiss of Death" after the tragic incident -- was never raced again. No other jockey would ride her.