Top 10 Greatest Upsets in Horse Racing History

Top 10 Greatest Upsets in Horse Racing History

Top 10 Greatest Upsets in Horse Racing History
Why do casual sports fans like horse racing so much?
One of the main reasons is the perception that anyone can win the race. Sports geeks can debate whether or not underdogs are more likely to win a major horse race than other events like an NBA Championship, a men’s NCAA basketball title, the Indianapolis 500 or The Masters. But this opinion persists largely due to two reasons: the average fan’s ignorance of the nuances of horse racing, and the precise quantification of the minuscule chances of a given horse winning the race.
It’s true that lots of people who bet on the ponies love to slap down a $2 bet on a horse with long odds. After all, it’s a low-risk, high-reward move: two bucks isn’t a huge investment for an opportunity to turn it into dozens of dollars – or perhaps even more than a Benjamin. It’s a bit like buying a lottery ticket – only with a vastly higher probability of cashing it in for a nice reward.
And for anyone who follows horse racing even casually, it’s a periodic occurrence to see a huge underdog somehow beat the odds and win a race. It’s a bit like reading about a hole-in-one at your local golf course, or a 300-game by a guy in your bowling league, or a half-court, buzzer-beating winning shot at a nearby high school or college basketball game. While these events are certainly rare, they do happen. And it’s doubly satisfying when you’re there to see it.
But every once in a long while, an earth-shattering upset comes along in the world of horse racing where it’s nearly impossible to find anyone who would have predicted it (much less ponied up cash to bet on such an outcome). It may have more to do with the competition in a given race rather than any negative assessment of a given horse’s abilities. Nevertheless, these are the upsets which find their way into U.S. horse racing lore.
Here are ten of the biggest upsets in the sport of horse racing in America:

10. Sarava, 2002 Belmont Stakes

Every sports fan loves a story where an underdog comes out of nowhere to win in front of a record crowd. This horse racing story has the record crowd part; 103,222 fans came to Elmont, New York to witness the 2002 edition of the Belmont Stakes (the attendance mark has yet to be broken). Sarava was an 0-for-3 two-year old in England when he was shipped back across the pond, where he then picked up his first win in November of 2001. Then after winning just one other race, he was tossed into the Belmont field along with War Emblem, who was running for a Triple Crown. Somehow, Sarava won the race – at 70-1 odds. He would never win another race again.

9. Dare and Go, 1996 Pacific Classic Stakes

You’re aware of the Champions Tour in men’s golf? On the “senior circuit” for horse racing, the Pacific Classic Stakes at Del Mar Racetrack in California is one of the crown jewels. It’s where horses three years or older vie for part of a $1 million purse. In 1996, fans flocked to the track to get a look at Cigar, which was trying to extend his winning streak to 17. Two competitors, Dramatic Gold and Siphon, were itching to end his amazing run. The race lived up to its billing as the trio became locked in a speed duel. But then something weird happened – all three horses tired out just long enough for 39-1 longshot Dare and Go to sneak by them and win the race.

8. Arcangues, 1993 Breeders’ Cup Classic

There’s an old joke about how French horses always run faster backwards because they’re used to retreating so much. But that assessment doesn’t describe Arcangues, who posted an impressive career on European grass tracks in the early ’90s. His handlers decided to bring him to the U.S. to run him on the dirt track of Santa Anita Park in California for the Breeders’ Cup Classic in 1993. It’s safe to say that nobody thought he would win, given that he posted mind-boggling odds of 133-1. But under the whip of last-minute jockey Jerry Bailey, Arcangues passed Bertrando on the homestretch – and became the biggest upset winner in Breeders’ Cup history.

7. J.O. Tobin, 1977 Swaps Stakes

This Maryland-bred thoroughbred was far from an unknown in the horse racing world. He finished his career with a dozen victories is 21 races and was the 1976 English Two Year Old Champion. Still, he wasn’t expected to do much the following year when he came back from Europe to race in the U.S. (yes, in California) at Hollywood Park Racetrack. After all, Seattle Slew was in the field fresh off his Triple Crown win and riding a nine-race winning streak. With famed jockey Bill Shoemaker riding him, J.O. Tobin put on a show. He not only beat Seattle Slew, he crushed him; beating every horse by an amazing eight lengths and just missing the track record. Seattle Slew came in fourth.

6. Angle Light, 1973 Wood Memorial Stakes

You probably have never heard of Angle Light, but you do know his stablemate: Secretariat. The reigning American champion was already the favorite in the 1973 Kentucky Derby. But the month before that, he was in Queens at Aqueduct Racetrack for the Wood Memorial Stakes. And this story demonstrates the unpredictability of horse racing: Secretariat developed an abscess under his lip hours before the race and took to the track not feeling 100%. That was enough for Angle Light, who never won a race without an early lead, to go wire-to-wire and win the Wood Memorial. Sham (shown above with Angle Light) finished second and Secretariat third. Secretariat went on to win the Kentucky Derby, with Angle Light finishing tenth.

5. Canonero II, 1971 Kentucky Derby

You know that you’re an underdog when the racetrack won’t even let wagerers bet on you to win. Canonero II was actually listed as one of half a dozen horses on a mutual bet in the ’71 Kentucky Derby (the other five finished in the bottom five spots). Born with a crooked foreleg and shipped to Venezuela to train, Canonero II flew below the global thoroughbred radar prior to 1971. Many observers even wondered why the horse was in the Derby field at all. But little did they know that Canonero II had already won a mile-and-a-quarter race in Venezuela. And despite running in 18th place out of 20 horses at the half-mile, Canonero II stormed past the field to reach the wire first and astonish the Churchill Downs crowd. Had he been listed individually on the betting board, he would have undoubtedly broken the track record for payouts. And he wasn’t done: Canonero II went on to win the Preakness Stakes as well.

4. Dark Star, 1953 Kentucky Derby
Eric Guerin, Hank Moreno

No, it’s not where the term “dark horse” comes from, but maybe it should be. Dark Star had some game, winning the Derby Trial at Churchill Downs just days before the ’53 Kentucky Derby. But he was going up against Native Dancer, the powerful stallion known as “the Grey Ghost” who was 11-for-11 going into the race. Again, the sport’s randomness cost Native Dancer; he was bumped on the first turn while Dark Star, a near 25-1 underdog, sprinted to the lead. Native Dancer made a great run to the finish, but lost to Dark Star by a head. It turned out to be the Grey Ghost’s only loss in his 22-race career.

3. Jim Dandy, Travers Stakes of 1930

The great thing about Jim Dandy is that he competed in a whopping 141 races in his 12-year career. The bad news? He finished last in the majority of them and notched only seven victories. So you can imagine that he wasn’t even an afterthought at the Travers Stakes in 1930, especially given the fact that the great Gallant Fox, the year’s Triple Crown champion, was there. But Jim Dandy had a secret weapon: his so-called “eggshell hooves,” which can cause pain for horses on fast tracks but were perfectly suited for mud. On race day, rain fell off and on that day, the Saratoga Springs track was shin-deep in goo. The conditions enabled Jim Dandy, a 100-1 longshot (whom some bookies even listed at 500-1), to take control at the top of the stretch and cruise to an eight-length victory. The feat was so amazing that officials named a race the Jim Dandy Stakes in 1964.

2. Donerail, 1913 Kentucky Derby

In the most storied horse race in America, this is considered to be one of the biggest upset in history. The Kentucky horse had deep local roots with owner/trainer Thomas P. Hayes of Augusta and jockey Roscoe Goose, a 22-year old from Louisville; but he was still only given a 91-1 shot to win the 1913 Derby. During the race, favorite Ten Point ran out to an early lead at a blistering pace with Donerail in sixth. But as Ten Point started to tire, Donerail picked up speed and caught the frontrunner on the home stretch, then beat him to the wire by half a length. Not only did Donerail become the biggest longshot ever to win at Churchill Downs, he did it in a track record time. (Side note: Donerail wasn’t even the biggest underdog in the race. That honor went to sixth-place finisher Lord Marshall, at 183-1.)

1. Upset, 1919 Sanford Memorial Stakes

Contrary to popular myth, this event did not inspire the term “upset” to be used to describe a surprising victory. But the irony still puts this accomplishment at the top of the list simply because of the horse that was beaten: Man O’ War, whom some claim to be the greatest racer ever. Man O’ War never lost in his 21 races – except in 1919 at this Saratoga Springs race. And you could even put an asterisk by this loss, because when the starting gates opened, Man O’ War was still circling behind the starting line facing away from the other horses. Despite his misfortune, Man O’War still charged to the front of the pack; but just missed overtaking Upset by half a length. (To be fair, the result wasn’t wholly unexpected; Upset had finished in the money in his previous three races, including a place against Man O’ War at the same track previously.)
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