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10 Shocking Upsets In Horse Racing

The word “upset” can be defined as “an unexpected result or situation, especially in a sports competition”. Unexpected results happen all the time in horse racing and they are always cause for excitement.

Take a look back on some of these longshot winners in horse racing.

1. Upset defeats Man o’ War in the 1919 Sanford Memorial. Man o’ War is regarded as the greatest racehorse of all time. This breathtaking, monstrous chestnut won 20 of his 21 starts during his career in 1919 and 1920. His sole defeat occurred during his two-year-old season. There were no starting gates at Saratoga in 1919. Instead, horses stood behind a barrier of webbing that would be raised at the start. Without a solid stall to keep horses straight as we have in our starting gates today, many horses would circle behind the gate and the starter would have to wait until each horse was straight behind the barrier before starting the race. However, some accounts say that Man o’ War was standing sideways when the barrier lifted. Others say that he was standing in the opposite direction completely. Whatever the case, Man o’ War had a bad start while a horse named Upset got away perfectly. The large chestnut tried his hardest to win the race but ultimately fell just a neck short of victory behind Upset while carrying 15 more pounds than his rival. “Man o’ War proved himself by running unquestionably the best,” the Daily Racing Form published on August 14, 1919. “It was Upset’s advantage at the start, coupled with fifteen pounds weight concession, a perfect ride he received from Knapp, and the success in saving ground on the stretch turn that brought about his triumph over Man o’ war. Had the race been a sixteenth farther the finish would have been reversed.” “Good colt though that he proved, few outside of his immediate connections and their friends considered him capable of beating Man o’ War.” This upset by the aptly named racehorse Upset was the only loss of Man o’ War’s storied career and helped cement Saratoga Race Course as the “graveyard of champions”. Upset went on to narrowly finish second in both the Kentucky Derby and Preakness Stakes and won the Havre de Grace Consolation Handicap and Latonia Derby.

The appropriately named Upset, who handed the legendary Man o' War his only defeat in the 1919 Sanford Memorial. Horse Racing upsets.
The appropriately named Upset handed the legendary Man o' War his only defeat in the 1919 Sanford Memorial. Public Domain.

2. Sarava ends War Emblem’s bid for the Triple Crown in the 2002 Belmont Stakes. War Emblem was poised to become the 12th Triple Crown winner in history when he entered the starting gates for the Belmont Stakes in 2002. The Bob Baffert trained nearly-black colt captured both the Kentucky Derby and Preakness Stakes in impressive, front-running fashion. Baffert had trained two other Triple Crown hopefuls that finished just short of victory in years prior to War Emblem’s bid: Silver Charm lost the Triple Crown by ¾ lengths in 1997 and Real Quiet lost by a nose in 1998. A record crowd packed into Belmont Park to see if War Emblem could break the 24-year-long Triple Crown drought. Unfortunately, War Emblem stumbled badly at the start of the race and had to use up quite a bit of energy to get into a good placing in mid-pack. Sarava, the longest shot on the board at 70-1, raced just behind him in 5th. War Emblem was exhausted by the time the field hit the top of Belmont’s long stretch and began to fade back into the pack. Meanwhile, Medaglia d’Oro took the lead and Sarava came up on the outside of him. These two ensured the race would not be boring, even without a Triple Crown winner; they battled fiercely down the length of the stretch with Sarava prevailing by about a neck. Sarava was the biggest longshot in history to win the Belmont Stakes. Bob Baffert and jockey Victor Espinoza teamed up again in 2015 and got redemption for this loss by winning the Triple Crown with American Pharoah. [Video: Watch Sarava win the Belmont Stakes at odds of 70-1]

3. Wild Again wins the inaugural Breeders’ Cup Classic at 31-1. The Breeders’ Cup Classic is one of the most anticipated races of the year. 1984 was the inaugural year of this now iconic race and it was slated to be a good one. Among the most established runners were Slew O’ Gold, 1983’s Champion Three Year Old Male and winner of the Whitney Stakes, Marlboro Cup, Woodward Stakes, and Jockey Club Gold Cup; and Gate Dancer, the winner of the Preakness Stakes, Omaha Gold Cup, and Super Derby. Wild Again was a good racehorse himself, having won the New Orleans Handicap (G2), Oaklawn Handicap (G2), and Meadowlands Cup (G1), but he was dismissed in the running of the Breeders’ Cup Classic after finishing 3rd in an Allowance race at Bay Meadows just two weeks before the Breeders’ Cup. Wild Again took the lead at the start of the race and he and two other pace pressers separated themselves from the rest of the field. Slew O’ Gold moved up from 5th into 2nd as the horses approached the stretch and Gate Dancer came running after the two of them. The horses straightened up for their stretch run, Wild Again on the inside and Slew O’ Gold on his outside. They went stride for stride down the racetrack before, finally, Gate Dancer moved up alongside them and the trio began an exhilarating battle. There was nothing separating them down the stretch. Slew O’ Gold was in tight between Wild Again and Gate Dancer and was taking quite a few bumps from the latter. When the horses came under the wire, Wild Again had his nose in front, defeating the two favorites as a dismissed longshot. Gate Dancer finished 2nd but was ultimately disqualified into 3rd for bumping Slew O’ Gold. This inaugural edition of the Breeders’ Cup Classic set the tone for many more thrilling runnings of this race. [Video: Watch the three-horse stretch battle in the 1984 Breeders’ Cup Classic]

4. Arcangues wins the 1993 Breeders’ Cup Classic at odds of 133-1. Wild Again wasn’t the longest shot to win the Breeders’ Cup Classic. That honor belongs to Arcangues. Arcangues was a brilliant racehorse over in Europe, having won three Group 1 races, but because those wins came over a turf course, bettors sent him into the starting gates at the huge odds of 133-1. Jockey Jerry Bailey got the mount on Arcangues last minute after the colt’s originally scheduled rider Mike Smith opted to ride Devil His Due. Bailey couldn’t understand instructions from the horse’s French trainer and didn’t even know how to pronounce his horse’s name. Nevertheless, he and Arcangues hugged the rail throughout the running of the Breeders’ Cup Classic and shot through a hole at the top of the stretch. With powerful strides, Arcangues blew past the leader and race-favorite Bertrando to become the huge upset winner of the 1993 Breeders’ Cup Classic. [Video: Watch Arcangues shock the world in the Breeders’ Cup Classic]

5. Donerail wins the 1913 Kentucky Derby at odds of 91-1. Donerail’s owner Thomas P. Hayes felt that his horse didn’t belong in the Kentucky Derby. The colt only won 4 of 18 races as a two-year-old and hadn’t won any of his 3 races as a three-year-old, though he did finish second in the Blue Grass Stakes. Hayes felt that his horse was simply outclassed and because the Kentucky Derby wasn’t as prestigious or rich as it is today (it was only the 39th running of the race and the purse was only $6,600), Hayes didn't see the need to run. However, Donerail’s jockey Roscoe Goose was determined to convince Hayes to run him in the Derby. Hayes initially refused, telling Goose to seek another mount, but Goose would not give up. Another one of Hayes’ good friends William J. Treacy offered to pay the colt’s entry fee if Hayes ran Donerail. Finally, Hayes gave in and entered Donerail into the Derby. But getting there was going to be quite the task. There was no available stall space at Churchill Downs, so Donerail would have to be stabled three miles away at Douglas Park and then walk the entire way to Churchill Downs on dirt and cobblestone streets. Despite it all, Donerail won the Kentucky Derby by ½ lengths in then stakes record time of 2:04 ⅘ . He is still the longest shot to ever win the run for the roses.

“I regard it as the greatest afternoon in my whole life for the reason that I was born and reared in Louisville and I have won Louisville’s greatest race,” jockey Roscoe Goose said after the race. “I will never forget this day as long as I live.” Read Donerail’s entire story in our article “Donerail: The 91-1 Longshot Kentucky Derby Winner”.

91-1 Kentucky Derby winner Donerail, longest shot to ever win the Kentucky Derby. Horse Racing Upsets.
Donerail is the longest shot to ever win the Kentucky Derby. Public Domain.

6. Keen Ice hands American Pharoah defeat in the 2015 Travers Stakes. American Pharoah came into the Travers Stakes (G1) after having won 8 consecutive races, including all three races in the Triple Crown series. At the time, the biggest threats to him winning seemed to be Texas Red and Frosted. Few people expected Keen Ice to spring an upset over the Triple Crown winner despite the fact that he had finished a fast-closing 2nd to Pharoah in the Haskell Invitational (G1). However, Frosted pressed a fast pace out of American Pharoah, leaving the Triple Crown winner tired in the stretch. Though he was still able to fend off Frosted, he couldn’t hold off Keen Ice, who was closing quickly down the stretch. The crowd held their breath as they watched their Triple Crown champion get run down by the 16-1 longshot that hadn’t won a race since breaking his maiden. Keen Ice’s victory over American Pharoah was just another that proved Saratoga’s reputation as the “graveyard of champions”. Keen Ice's son Rich Strike followed in his father's upsetting footsteps to win the Kentucky Derby at odds of 80-1 in 2022. [Video: Watch Keen Ice run down American Pharoah at odds of 16-1]

7. Rockamundo captures the 1993 Arkansas Derby at 108-1. Rockamundo entered the 1993 Arkansas Derby with only one win in nine starts. He had lost his previous two races leading up to the Arkansas Derby by a combined 22 lengths and looked firmly out of depth in the graded event. “Anybody who looked at the Daily Racing Form would say that we were crazy to run in this race,” Rockmundo’s owner Gary West told the Los Angeles Times. Rockamundo was a nervous horse and was always unwilling during his morning workouts. He also had a bad habit of “holding his breath” during his races. Rockamundo never trained well, so it was quite surprising when he turned in a bullet five-furlong work while under jockey Calvin Borel for the first time. “I thought they were doing the wrong things with this horse,” Borel said. “They said he was having trouble breathing. I think it was because they were taking the horse back in his races. He’s a nervous horse, and that might have been why he had been holding his breath. I just let him roll once we got started.”

It was thanks to the suggestion of the then 29-year-old Borel that Rockamundo was finally able to show what he was capable of in the Arkansas Derby. Instead of taking the horse to the back of the pack, Borel let Rockamundo run just off the pacesetter Foxtrail the whole way. At the top of the stretch, Foxtrail came slightly off the trail and Rockamundo and Borel slipped right through the opening and won. "I try to be confident every time, but common sense told me this one didn't have a shot," Borel told the New York Times. "So much for common sense."

8. Take Charge Brandi upsets the 2014 Breeders’ Cup Juvenile Fillies at 60-1. Take Charge Brandi had only won one race leading into the Breeders’ Cup Juvenile Fillies: her maiden breaking performance at Churchill Downs. Though she was 2nd in her next start, the Schuylerville Stakes (G3), she did not even finish in the top four in any of her next three starts. In fact, she finished 8th in her start just prior to the Breeders’ Cup, the Alcibiades Stakes (G1). Despite this, she had been training well in her lead-up to the Breeders’ Cup and her trainer D. Wayne Lukas thought that she had a shot - not necessarily to win, but to at least finish in the money. Lukas was right to believe in his filly; Take Charge Brandi set the pace under jockey Victor Espinoza and was strong enough to hold off bids from Top Decile, Wonder Gal, and Feathered in the stretch. “Dr. Bill Caton, who saved (son) Jeff's life, bet her heavy – he won't be able to carry it out in a shopping bag,” Lukas said after the race. “This is the most exciting one (win) yet.” [Video: Watch Take Charge Brandi win the Breeders’ Cup Juvenile Fillies]

9. Wild Syn captures the 1995 Blue Grass Stakes at odds of 30-1. Wild Syn’s sire Wild Again was known for winning the inaugural Breeders’ Cup Classic at odds of 31-1. Wild Syn memorably lived up to his pedigree by capturing the Blue Grass Stakes at odds of 30-1. Wild Syn entered the Blue Grass Stakes with two wins in five starts, one being his maiden breaking performance and the other being an Allowance win, both at Gulfstream Park. He traveled to Keeneland to contest in the Blue Grass (G2) after a 3rd place finish in the Holy Bull Stakes and looked as though he could be easily beaten by top contenders like the eventual Kentucky Derby winner Thunder Gulch as well as Suave Prospect and Tejano Run. But Wild Syn wasn’t scared of his tough competitors. He took the lead at the start of the race and never looked back, bounding away to a 2 ½ length victory over the favored Suave Prospect. [Video: Watch Wild Syn win the Blue Grass Stakes]

10. Mine That Bird wins the 2009 Kentucky Derby at 50-1.

One of the most famous longshot winners in horse racing history is Mine That Bird, who captured the 2009 run for the roses at odds of 50-1.

Unlike many of the other longshot winners listed here, Mine That Bird actually began his racing career with a lot of wins. After failing to win his first start, Mine That Bird went on a four-race win streak at Woodbine that included two stakes and one graded stakes, the Grey Stakes (G3). However, a 12th in the Breeders’ Cup Juvenile and two losses in stakes company at Sunland Park after that made many bettors believe that Mine That Bird had no shot at winning the Kentucky Derby.

He entered the starting gates as the third-longest shot in the race. Mine That Bird raced in the back of the pack, far off the leader Join The Dance. But as the horses approached the stretch, Mine That Bird and jockey Calvin Borel came soaring up the rail at incredible speeds. They picked off horses like they were standing still until finally, at about mid-stretch, the mud-covered duo emerged at the front.

"He took me to a spot and I saw a wall of horses and I said, 'What ya gonna do, Calvin?" Borel said in an interview with Times Union. "That little horse, his feet were rattlin'. Damn. He did the impossible."

They kept running and running until they were 6 ¾ lengths in front. It was the largest winning margin in over 60 years and until the recent 80-1 Kentucky Derby win by Rich Strike, Mine That Bird tied 2005 Kentucky Derby winner Giacomo as the second-longest shots to win the run for the roses.

"I remember seeing a horse going down the rail, and I was like, 'Who is that?,” jockey Mike Smith, who was riding Chocolate Candy, recalled. “It just shows that an underdog can win in this game. You can beat kings and queens, man. That's what is so great about racing.”

Mine That Bird is still one of the most known and loved longshot winners today.

[Video: Watch the trailer for the movie “50 To 1” made about Mine That Bird]


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