How One Upset Scarred the Legacy of History’s Greatest Thoroughbred

Why you should care

Urban legends aside, this was one unexpected outcome to a horse race.

David and Goliath: Sometimes the little guy wins. David and Goliath: Sometimes the little guy wins.

Want to have a sports conversation around a topic that could go on for days and days — because there can never truly be a conclusion? 

Light a fire under “biggest upsets in sports history,” and step aside and see what happens. You’ll no doubt hear somebody mention the Mike Tyson and James “Buster” Douglas fight from 1990, which featured the journeyman Douglas, a 42-1 underdog, knocking out big, bad “Iron” Mike Tyson in the 10th round. The 1980 “Miracle on Ice” game at the XIII Olympic Winter Games might also get a mention, where the underdog U.S. hockey team beat the four-time defending gold medal-winning Soviet team.

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Buster Douglas knocks out Mike Tyson in 1990.

Source Sadayuki Mikami/AP

But etymologists will point you to a certain horse race — run a hundred years ago this August — that apocryphally spawned the term itself. On Aug. 13, 1919, at Saratoga Race Course, a horse named Upset crashed right through unbeatable odds when he defeated the heavily favored Man o’ War in the seventh running of the Sanford Memorial Stakes. Man o’ War, considered one of racing’s enduring legends, had never lost a race before that day and never would again.  

“People who were there have different accounts,” says Brien Bouyea, communications director at the National Museum of Racing and Hall of Fame in Saratoga Springs, New York. “At the start of the race, there were several false starts, and by all accounts, the [race] starter had a tough time. He was a substitute, and up there in age. And, another account was that Man o’ War was standing behind the starting line and turned sideways, which lost him some ground.”

 

The two horses would face each other six more times, with Upset losing every single time. That, says, Bouyea, only fueled conspiracy theories about Upset’s upset win. Some speculated that the two jockeys — Willie Knapp rode Upset and Johnny Loftus rode Man o’ War — might’ve been in cahoots. And even though no evidence ever substantiated the rumor, and Knapp himself would later say he got paid only $25 for riding the winning horse, Loftus was denied a license to ride after that race, and neither man would ride again. Both would be banned from racing for life at the end of that 1919 season, a banning The Jockey Club never made public. “I don’t think he would have taken $100,000 to throw that race,” Knapp said of Loftus in a 1966 interview with Sports Illustrated.

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Upset crashed right through unbeatable odds when he defeated the heavily favored Man o’ War in the seventh running of the Sanford Memorial Stakes.

Source National Museum of Racing and Hall of Fame

But this was 1919, and conspiracies were emblematic of the time, explained veteran sports journalist and author Steve Wulf, a founding editor of ESPN The Magazine. “It was the year of the Black Sox Scandal [in which eight members of the Chicago White Sox were accused of intentionally losing the 1919 World Series] so naturally those forces were at work.”

“The jockeys swore there was no conspiracy with them,” explains Bouyea. “And both were eventually inducted into the National Museum of Racing and Hall of Fame, so there’s that.” But one thing that is sure, he says, is that an upset victory isn’t named after Upset the horse.  

“It wasn’t a new thing — but this horse having that name certainly played into it, and it was sort of the perfect storm that popularized the term,” he says. The use of the word in horse racing dates to the 1870s and it had been used to mean more general overturnings since at least the turn of the 19th century.  

Whatever your take, history’s greatest upset is a discussion that won’t go away. But while you banter with your friends, just know that the biggest upset in sports history is one from the not-too-distant past; it happened in the 2018 NCAA Men’s Tournament, when No. 16 University of Maryland, Baltimore County (UMBC) knocked off No. 1-seeded Virginia.

Now that was madness. Talk amongst yourselves.

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