Biggest Long Shot Winners in Triple Crown Horse Racing History

Rich Strike is not the first horse to shock the world in a big race at the Kentucky Derby, Preakness Stakes or Belmont Stakes.

Rich Strike shocked the sports world when he won the 2022 Kentucky Derby. He entered the race with 80-1 odds and became one of the biggest underdogs to win a Triple Crown race.

Every now and then, a horse like Rich Strike comes through and surprises everyone by taking down the favorites in the Kentucky Derby, Preakness Stakes or Belmont Stakes — the three races that make up the Triple Crown and the three most prestigious races in horse racing.

Going back to the late 1800s, gamblers and horse racing fans alike have been left ripping up their tickets and shaking their heads at horse racing upsets, while those lucky ones who placed long shot bets have walked up to the booth to cash in some of the biggest paydays of all time.

These are the biggest long shot winners in horse racing history at the Kentucky Derby, Preakness Stakes and Belmont Stakes.

30. I’ll Have Another, 2012 Kentucky Derby

I'll Have Another ridden by jockey Mario Gutierrez

David J. Phillip / AP Photo

Odds: 12-1

Jockey: Mario Gutierrez

Owner: J. Paul Reddam

Bottom line: I’ll Have Another was an upset winner — kind of — because the field at the 2012 Kentucky Derby was so talented. I’ll Have Another chased down Bodemeister down the stretch at Churchill Downs for the victory.

I’ll Have Another also won the Preakness but never got a shot at the Triple Crown when he was scratched the day before the Belmont Stakes with tendinitis and retired from racing.

29. Bernardini, 2006 Preakness Stakes

Bernardini ridden by jockey Javier Castellano

Jim Dietz / AP Photo

Odds: 13-1

Jockey: Javier Castellano

Owner: Darley Stables

Bottom line: Bernardini’s upset at the 2006 Preakness Stakes was overshadowed by the fractured leg of Kentucky Derby winner Barbaro, which ultimately led to Barbaro’s death.

Citing the stress of becoming a champion horse so quickly, Bernardini’s owner, Sheikh Mohammed bin Rashid al Maktoum, the ruler of Dubai, made the decision to sit his horse out of the Belmont Stakes, meaning it was just the fourth time in 60 years neither the Kentucky Derby or Preakness winner was in the Belmont.

Bernardini was retired to stud later in 2006 and lived until 2021. As of 2022, Sheikh Mohammed’s net worth was estimated at $4 billion.

28. Shackleford, 2011 Preakness Stakes

John Bazemore / AP Photo

Odds: 13-1

Jockey: Jesus Castanon

Owners: Mike Lauffer and William D. Cubbedge

Bottom line: Shackleford was an interesting 13-1 long shot at the Preakness, especially after he finished fourth at the Kentucky Derby, where he was only overtaken late.

That finish, however, allowed Shackleford to win $1.15 million at the Preakness — $600,000 from the winner’s purse and another $550,000 in the Xpress Consolation Bonus, which paid out to a horse who’d also finished in the top three at either the Florida Derby or the Santa Anita Derby.

Shackleford followed up the win at the Preakness with a fifth-place finish at the Belmont Stakes. He was retired to stud duty in 2012 and sold to the Korean Racing Authority in South Korea in 2020.

27. Deputed Testamony, 1983 Preakness Stakes

Ed Reinke / AP Photo

Odds: 15-1

Jockey: Donnie Miller Jr.

Owner: Bonita Farm

Bottom line: There’s a special love for Deputed Testamony, who was the last of eight Maryland-born horses to win the Preakness Stakes — the Triple Crown race that occurs on its native soil.

In an interesting twist, Deputed Testamony’s owners did not have him race at the Kentucky Derby, instead making the Triple Crown debut at the Preakness, where he defeated Kentucky Derby winner Sunny’s Halo.

Deputed Testamony died in 2012, at 32 years old, and was the last living horse to win a Triple Crown race in the 1980s.

26. Oxbow, 2013 Preakness Stakes

Matt Slocum / AP Photo

Odds: 15-1

Jockey: Gary Stevens

Owner: Calumet Farm

Bottom line: The sire of Breeders’ Cup Classic winner Awesome Again, Oxbow was more known for his unreliability as a racehorse leading up to the 2013 Preakness Stakes. But the horse shook off that reputation with an upset win at Pimlico followed by a second-place finish at the Belmont Stakes.

It was a momentous win for famed stable Calumet Farm, which hadn’t had a Triple Crown winner since 1968. It was also a comeback for jockey Gary Stevens, who came out of a seven-year retirement to ride Oxbow and won his first Triple Crown race in 13 years.

Oxbow sired Hot Rod Charlie, who finished in second place at both the Kentucky Derby and Belmont Stakes in 2021.

25. Lil E Tee, 1992 Kentucky Derby

John Swart / AP Photo

Odds: 17-1

Jockey: Pat Day

Owner: W. Cal Partee

Bottom line: Some expert jockeying by Pat Day helped lift underdog Lil E Tee to the 1992 Kentucky Derby win. Day essentially used hard-charging Arazi as a draft horse until Arazi tired out down the stretch, then overtook the field for the win.

Lil E Tee finished fifth in the Preakness, then missed the Belmont with a lung infection. He recovered from arthroscopic surgery to win the Grade II Razorback Handicap in 1993 before he retired.

Lil E Tee died in 2009, after he sired 19 stakes winners that accumulated almost $10 million in career earnings.

24. Bee Bee Bee, 1972 Preakness Stakes

AP Photo

Odds: 18-1

Jockey: Eldon Nelson

Owner: William S. Farish III

Bottom line: Born in Maryland, Bee Bee Bee is one of just eight horses born in the state to win the Preakness and one of just 11 Maryland-born horses to win a Triple Crown race.

The grandson of 1928 Kentucky Derby winner Reigh Count, Bee Bee Bee was actually the property of former Illinois racing commissioner William Miller, who had to liquidate his assets following his role in a bribery scandal involving former Chicago mayor Richard J. Daley.

Bee Bee Bee held off Kentucky Derby winner Riva Ridge in the Preakness Stakes but didn’t run in the Belmont Stakes, which Riva Ridge also won.

23. Display, 1926 Preakness Stakes

AP Photo

Odds: 19-1

Jockey: John Maiben

Owner: Walter J. Shaw Jr.

Bottom line: Display joins the ranks of Seth Curry, Gerald Wilkins and Dom Dimaggio as forgotten pro sports siblings. He’s the brother of legendary racehorse Man O’War, who is widely considered the greatest racehorse of all time.

Display grabbed his own share of the spotlight in 1926 when he won the Preakness Stakes, going off at 19-1 odds. He raced for longer than most champion horses, winning six races as a 4-year-old in 1927 and competing in races until he was 6 years old.

One of Display’s children, Discovery, was the runner-up in the 1934 Kentucky Derby.

22. Commendable, 2000 Belmont Stakes

Commendable racing at the Belmont Stakes

Horse Racing / YouTube

Odds: 19-1

Jockey: Pat Day

Owner: Bob and Beverly Lewis

Bottom line: Commendable had an incredibly short career as a racehorse. He only raced 12 times in his career and won twice, including the Belmont Stakes upset victory in 2000.

There was a reason Commendable was such an underdog at the Belmont. He lost in all four races leading up to the Triple Crown races, finished 17th out of 19 horses in the Kentucky Derby, and his owners didn’t even run him in the Preakness Stakes.

Commendable went out to stud on a Kentucky farm for five years before going to a stud farm in South Korea, where he remained until he died from colic in 2014.

21. Coventry, 1925 Preakness Stakes

FriendOfRacing / Twitter

Odds: 21-1

Jockey: Clarence Kummer

Owner: Gifford A. Cochran

Bottom line: Legendary trainer Bill Duke was in charge of Coventry, although he only competed in five races in his lifetime and won just once, going off as a 21-1 underdog at the 1925 Preakness Stakes.

Coventry was the biggest long shot winner at the Preakness for 50 years, until Master Derby in 1975. His body began to break down in his next race, and he was retired to stud but had little success there.

20. Gato Del Sol, 1982 Kentucky Derby

AP Photo

Odds: 21-1

Jockey: Eddie Delahoussaye

Owner: Hancock and Peters

Bottom line: Gato Del Sol was the son of a Chilean racehorse, Cougar, and one of our least favorite horses on the list.

Why don’t we like Gato Del Sol? After he won the Kentucky Derby in an upset, Gato’s trainers decided to not even run in the Preakness Stakes because it was a shorter track and to focus on the Belmont Stakes, where Gato finished second.

Nothing like getting a shot at history and deciding not to go for it. Cowards.

19. Animal Kingdom, 2011 Kentucky Derby

David J. Phillip / AP Photo

Odds: 21-1

Jockey: John Velazquez

Owner: Team Valor International

Bottom line: Animal Kingdom pulled off the huge upset at the 2011 Kentucky Derby and came within one spot of having a shot at the Triple Crown after he finished in second place at the Preakness Stakes.

Animal Kingdom’s career was sidelined by injuries shortly after his 3-year-old season, but bounced back to become the only horse to win a Grade 1 race as a 5-year-old.

18. Master Derby, 1975 Preakness Stakes

keeneland / Twitter

Odds: 23-1

Jockey: Darrell McHargue

Owner: Golden Chance Farm

Bottom line: Master Derby’s win at the Preakness Stakes probably shouldn’t have been as big of a surprise as it was. He’d won a pair of races as a 2-year-old and finished fourth at the Kentucky Derby.

Master Derby was a winner at his core. He won five races in 1975, including the Preakness, and added three more wins in 1976.

17. Ruler on Ice, 2011 Belmont Stakes

Mark Lennihan / AP Photo

Odds: 25-1

Jockey: Jose Valdivia Jr.

Owner: George and Lori Hall

Bottom line: Ruler on Ice was at his best when the track was not. Out of his three career wins, two came on sloppy, muddy tracks.

Ruler on Ice’s greatest win came in the slop, at the 2011 Belmont Stakes. Ruler came in as a 25-1 underdog in large part because he hadn’t run in the previous two Triple Crown races at the Kentucky Derby or Preakness Stakes.

Ruler on Ice was the most unusual of Triple Crown winners as a geldling — meaning he was castrated.

16. Exterminator, 1918 Kentucky Derby

Ramsey_Farm / Twitter

Odds: 29-1

Jockey: Willie Knapp

Owner: Willis Sharpe Kilmer

Bottom line: Exterminator wasn’t the only Kentucky Derby winner in his family. Older brother Donerail also won the 1913 Kentucky Derby. But more on him later.

Exterminator was sold to owner Willis Sharpe Kilmer as a “workhorse” right before his 3-year-old season began and was thought of mainly as a way to keep Kilmer’s prized horse, Sun Briar, ready for competition. Kilmer commonly referred to Exterminator with disdain. Mainly he called him “that goat.”

Guess what happened next? Sun Briar got ringbone right before the 1918 Kentucky Derby, and Kilmer begrudgingly raced Exterminator, who took off down the stretch for the upset win. Kilmer rewarded him by running him until he was 9 years old.

In an interesting twist, Exterminator lived until the ripe old age of 30 and died in 1945, outliving Kilmer by five years.

15. Proud Clarion, 1967 Kentucky Derby

Bob Ussery with Proud Clarion in the winner's circle

AP Photo

Odds: 30-1

Jockey: Bob Ussery

Owner: Darby Dan Farm

Bottom line: Proud Clarion showed little promise in races as a 2-year-old, finishing in third place in a few minor sprints. But he showed enough promise that 30-1 odds at the 1967 Kentucky Derby seemed like a stretch after he finished as a runner-up at the Blue Grass Stakes leading up to the main event.

Proud Clarion followed up his upset win at the Kentucky Derby by finishing third at the Preakness Stakes and third at the Belmont Stakes.

14. Charismatic, 1999 Kentucky Derby

Patti Longmire / AP Photo

Odds: 31-1

Jockey: Chris Antley

Owner: Bob and Beverly Lewis

Bottom line: Charismatic is unique on this list in that he won multiple Triple Crown races.

Charismatic shocked the racing world as a 31-1 upset winner at the 1999 Kentucky Derby, then followed that up with a win at the Preakness Stakes, giving him a shot at the Triple Crown.

In the lead at the Belmont Stakes, jockey Chris Antley pulled up and dismounted Charismatic, famously cradling the horse’s fractured leg in his hands.

13. Apollo, 1882 Kentucky Derby

ARodriguezVera / Twitter

Odds: 32-1

Jockey: Babe Hurd

Owner: Morris and Patton

Bottom line: The oldest winner on the list, it’s been 140 years since Apollo won the Kentucky Derby in 1882 as a 32-1 underdog.

One interesting fact about Apollo is he didn’t race as a 2-year-old. He was the only Kentucky Derby winner not to do so until Justified won in 2018.

The year after the Kentucky Derby, Apollo won 14 races out of 30 starts in 1883 and was retired to a saddle horse in 1884, but died of lockjaw in 1887.

12. Gallahadion, 1940 Kentucky Derby

AP Photo

Odds: 35-1

Jockey: Carroll Bierman

Owner: Milky Way Farm

Bottom line: Gallahadion was one of two grandsons of 1928 Kentucky Derby winner Reight Count to win Triple Crown races, along with 1972 Preakness Stakes winner Bee Bee.

Gallahadion was the culmination of one incredibly rich woman’s racing dream. Ethel V. Mars of the Mars family candy fortune reportedly spent $500,000 on eight horses in the years leading up to the 1940 Kentucky Derby.

Unfortunately for Mars, when one of her horses finally did win the Kentucky Derby, she wasn’t there. She was home sick with a cold.

11. Pass Catcher, 1971 Belmont Stakes

jfarache / Twitter

Odds: 35-1

Jockey: Walter Blum

Owner: October House Farm

Bottom line: Venezuelan colt Canonero II was the favorite to win the Belmont Stakes and bring the Triple Crown back to Venezuela, following wins at the Kentucky Derby and Preakness Stakes, but Pass Catcher played spoiler at 35-1 odds in front of a record crowd of 80,000 fans.

In an incredible addendum to Pass Catcher’s victory, jockey Walter Blum said he’d actually dropped his whip at the eighth pole but still rode the horse to victory.

10. Birdstone, 2004 Belmont Stakes

Edgar S. Prado riding Birdstone and Stewart Elliott riding Smarty Jones

Frank Franklin II / AP Photo

Odds: 36-1

Jockey: Edgar Prado

Owner: Marylou Whitney Stables

Bottom line: Birdstone has one of the more impressive lineages of any horse on this list. He was sired by 1996 Kentucky Derby winner Grindstone, who was sired by 1990 Kentucky Derby winner Unbridled.

Birdstone grabbed his own piece of horse racing history in 2004 with his win at the Belmont Stake, where Smarty Jones was trying to win the Triple Crown but finished second to Birdstone.

Birdstone has sired some memorable champions since he retired from racing, including 2009 Kentucky Derby winner Mine That Bird and 2009 Belmont Stakes winner Summer Bird.

9. Da’Tara, 2008 Belmont Stakes

Jim Dietz / AP Photo

Odds: 38-1

Jockey: Alan Garcia

Owner: Robert V. LaPenta

Bottom line: Big Brown was the favorite at the Belmont Stakes and had his eyes on the Triple Crown after winning the Kentucky Derby and Preakness Stakes before Da’Tara played spoiler.

What’s interesting about Da’Tara is that win at the Belmont was the only major win of his career and the last win of his career in any race. By 2011, the horse was put out to stud in Florida and later moved to a farm to stud in Venezuela.

8. Giacomo, 2005 Kentucky Derby

Al Behrman / AP Photo

Odds: 50-1

Jockey: Mike Smith

Owner: Jerry and Ann Moss

Bottom line: Giacomo was an oddity at the 2005 Kentucky Derby, more recognized for being the horse owned by A&M Records co-founder Jerry Moss and being named for the son of musician Sting than anything else.

Giacomo showed he was much more than those weird facts and pulled off the upset at Churchill Downs. Breathing problems slowed Giacomo to a third-place finish at the Preakness Stakes and a seventh-place finish at the Belmont Stakes.

After Giacomo finished fourth at the 2006 Breeders’ Cup Classic, he was retired to stud.

7. Mine That Bird, 2009 Kentucky Derby

Al Behrman / AP Photo

Odds: 50-1

Jockey: Calvin Borel

Owner: Double Eagle Ranch

Bottom line: Mine That Bird pulled off a stunning upset at the Kentucky Derby in 2009, kicking off an unusual run through the Triple Crown races that year — first at the Kentucky Derby, second at the Preakness Stakes and third at the Belmont Stakes.

Mine That Bird was so far back at the Kentucky Derby that NBC announcer Tom Durkin missed seeing him at first, but the horse made up a stunning amount of ground by using the “ride the rail” technique.

Mine That Bird was sired by another long shot winner, Birdstone, who won the Belmont Stakes in 2004 at 36-1 odds.

6. Temperence Hill, 1980 Belmont Stakes

AP Photo

Odds: 53-1

Jockey: Eddie Maple

Owner: Loblolly Stable

Bottom line: It’s kind of amazing Temperence Hill ended up with such long odds at the Belmont Stakes in 1980. He’d already won a pair of Kentucky Derby prep races at the Rebel Stakes and Arkansas Derby.

Temperence and jockey Eddie Maple took down Kentucky Derby winner Genuine Risk and Preakness winner Codex at Belmont and was named the top 3-year-old of 1980. He was put out to stud in 1981 and spent 16 seasons breeding, where he sired 3 foreign champions, 39 stakes winners and 433 winners who totaled $26.5 million in career earnings.

Temperence Hill died in 2003.

5. Sherluck, 1961 Belmont Stakes

Joe Caneva / AP Photo

Odds: 65-1

Jockey: Braulio Baeza

Owner: Jacob Sher

Bottom line: Carry Back was gunning for a Triple Crown before upset winner Sherluck and jockey Braulio Baeza came through at stunning 65-1 odds for a win at the Belmont Stakes.

The key to Sherluck was Baeza. The horse was considered one of the favorites at the Kentucky Derby and Preakness Stakes but finished fifth at both races with different jockeys.

With Baeza back in the saddle, Sherluck won the Belmont while Carry Back finished seventh.

4. Country House, 2019 Kentucky Derby

Matt Slocum / AP Photo

Odds: 65-1

Jockey: Flavien Pratt

Owners: Mrs. J.V. Shields Jr., E. J. M. McFadden Jr. and LNJ Foxwoods

Bottom line: Country House authored one of the most bizarre wins in Kentucky Derby history. Maximum Security actually crossed the finish line first, but the win was overturned when Country House jockey Flavien Pratt properly reported Maximum Security for interference.

Country House developed a virus that kept him out of the Preakness, which was the first time since 1996 that the Kentucky Derby winner did not race in the Preakness. The ailment forced Country House out to pasture, and he never raced again.

3. Sarava, 2002 Belmont Stakes

dp_ahmed / Twitter

Odds: 70-1

Jockey: Edgar Prado

Owner: New Phoenix Stable

Bottom line: No one — no one — thought there was any stopping War Emblem in 2002 after the horse won races at the Kentucky Derby and Preakness Stakes and seemed set to become the Triple Crown winner at the Belmont Stakes.

Sarava shocked War Emblem at 70-1 odds in front of a record 103,000 fans, one of just two major wins in the horse’s career. Sarava went out to stud in Florida in 2005 and was sent to an equine retirement community in 2012.

2. Rich Strike, 2022 Kentucky Derby

Jeff Roberson / AP Photo

Odds: 80-1

Jockey: Sonny Leon

Owner: RED-TR Racing

Bottom line: Rich Strike’s win at the 2022 Kentucky Derby was the sort of stuff movies are made of. He was in 18th place after the first half-mile and had to overtake four horses from the inside out in order to win down the stretch.

Just eight months earlier, Rich Strike had been purchased by trainer Eric Reed for $30,000. The win at the Kentucky Derby paid out $1.86 million for the winner’s purse. Reed, watching from the stables, collapsed in shock after the win.

1. Donerail, 1913 Kentucky Derby

wydkaspodcast / Twitter

Odds: 91-1

Jockey: Roscoe Goose

Owner: Thomas P. Hayes

Bottom line: The greatest long shot winner in Triple Crown history was Donerail in 1913, and came in the first race where working-class people were finally allowed to bet, with the lowest bets allowed to come in at $2.

Donerail owner Thomas P. Hayes didn’t think entering his horse in the race was worth the expense it would incur, but jockey Roscoe Goose convinced him otherwise. Because of overcrowding in the Churchill Downs stables, Donerail was forced to walk three miles through Louisville on the day of the race.

Whatever the formula, it paid off big in front of a then-record 30,000 fans for a $6,600 winner’s purse — the equivalent of around $20,000 in today’s money.