Some of the most unexpected Triple Crown horse racing winner’s history

When Rich Strike won the Kentucky Derby in 2022, he stunned the sports world. He was one of the most underdogs to win a Triple Crown event when he entered the competition at 80-1 odds.

The Kentucky Derby, Preakness Stakes, and Belmont Stakes are three of the most prestigious races in horse racing, and now and then, a horse like Rich Strike comes through and surprises everyone by defeating the odds-on favorites.

Many people who bet on horses in the late 1800s were left scratching their heads when the horses they were backing came up short, while others who placed longshot wagers won some of the most significant prizes in the history of the sport.

The Kentucky Derby, the Preakness Stakes, and the Belmont Stakes have all been won by longshots.

The 2012 Kentucky Derby is on me again.

• The odds are 12-1.
• Mario Gutierrez is the rider.
• John Paul Reddam is the proprietor.

Overall, I’ll Have Another came out on top in the Kentucky Derby because the field was so good. At Churchill Downs, I’ll Have Another fought off the challenge of Bodemeister to win the race.

After winning the Preakness, I’ll Have Another was scratched from the Belmont Stakes the Day before because of tendinitis and retired.

The 2006 Preakness Stakes winner Bernardini

• Odds of 13-1
• Javier Castellano is the rider.
• Darley Stables is the owner of this property.

Bernardini’s victory in the 2006 Preakness Stakes was overshadowed by Barbaro’s leg injury, which ultimately led to Barbaro’s death.

Bernardini’s owner, Sheikh Mohammed bin Rashid al Maktoum, ruler of Dubai, decided to withdraw his horse from the Belmont Stakes due to the pressure of having a champion horse so quickly. This was only the fourth time in 60 years that the Kentucky Derby or Preakness winner did not run in the Belmont.

It was later in 2006 that Bernardini retired to the stud and died in 2021. $4 billion was Sheikh Mohammed’s fortune as of 2022.

The 2011 Preakness Stakes winner Shackleford.

• Odds of 13-1
• Jesus Castanon is the rider.
• Involved parties: Mike Lauffer and William D. Cubbedge

Overall, Shackleford was an intriguing 13-1 long shot in the Preakness after finishing fourth in the Kentucky Derby and only being overtaken late.

Despite that finish at the Preakness, Shackleford won $1.15 million—$600,000 from the winner’s purse and another $550,000 in the Xpress Consolation Bonus, which paid out to a horse that had also finished in the top three at either the Florida Derby or the Santa Anita Derby—to take home the $1.15 million total.

Shackleford finished fifth in the Belmont Stakes after winning the Preakness Stakes earlier in the year. For sale to the Korean Racing Authority (KRA) in South Korea, he retired to stud duty back in 2012.

The 1983 Preakness Stakes Deputized Witness

• 15-1 are the odds.
• It’s Donnie Miller Jr.’s turn as a jockey.
• Bonita Farm is the owner.

Bottom line: Marylanders have a soft spot in their hearts for Deputed Testamony, the eighth horse to win the Preakness Stakes – the only Triple Crown race to be held in the state.

Instead of competing in the Kentucky Derby, Deputed Testamony’s owners decided to have him compete in the Preakness Stakes, where he defeated Kentucky Derby winner Sunny’s Halo in a thrilling finish.

Deputed Testamony, the only remaining Triple Crown winner from the 1980s, died in 2012 at 32.

2014 Kentucky Derby Preakness Stakes runner-up Oxbow

• 15-1 are the odds.
• Gary Stevens, the horse’s rider
• Calumet Farm is the owner.

A Breeders’ Cup Classic-winning sire of Awesome. Oxbow’s unpredictability as a racehorse was well-known before the 2013 Preakness Stakes, though. However, after an unexpected victory at Pimlico and a second-place performance at the Belmont Stakes, the horse managed to shake off its bad image.

Calumet Farm, a legendary racing stable, has not won the Triple Crown since 1968 with this victory. Also making a comeback was jockey Gary Stevens, who rode Oxbow to victory and won his first Triple Crown in 13 years after retiring for seven years.

Hot Rod Charlie, a son of Oxbow, finished second in both the Kentucky Derby and Belmont Stakes in 2021, thanks to his sire.

Kentucky Derby, 1992, Lil E. Tee.

• 17-1 the odds
• Pat Day is the jockey for this race.
• Cal Partee, W. Cal

Lil E Tee’s 1992 Kentucky Derby victory was aided by Pat Day’s significant jockeying. As Arazi wore out in the stretch, Day could pull away from the field and win comfortably.

A lung ailment forced Lil E Tee to miss the Belmont Stakes, where she finished fifth in the Preakness. Before retiring in 1993, he recovered enough from arthroscopic surgery to win the Grade II Razorback Handicap.

Lil E Tee died in 2009, having sired 19 stake winners that earned over $10 million in total earnings.

Preakness Stakes, 1972, Bee Bee Bee.

• One-in-a-hundred chance
• Eldon Nelson is the rider of this race.
• W. S. Farish III, III, William S

Bee Bee Bee is one of just eight Maryland-bred horses to win the Preakness Stakes and one of only eleven Maryland-bred horses to capture the Triple Crown.

Ex-Illinois racing commissioner William Miller had to liquidate his assets after being implicated in a corruption scandal with former Chicago Mayor Richard J. Daley. Bee Bee Bee was the property of Miller.

At Preakness Stakes, Bee Bee Bee beat Kentucky Derby winner Riva Ridge; nevertheless, at Belmont Stakes, Bee Bee Bee did not race.

The 1926 Preakness Stakes are on Display.

• Odds of 19-1
• John Maiben is the jockey for this race.
• Proprietor’s Name: Walter J Shaw Jr.

Display joins the likes of Seth Curry, Gerald Wilkins, and Dom DiMaggio as a forgotten pro sports brother. Her brother, famed racehorse Man O’War, has long been regarded as racing’s all-time great.

In 1926, Display became the first horse to win the Preakness Stakes with 19-1 odds. As a 4-year-old, he won six races and continued to race until he was six years old, a record for a champion horse.

The 1934 Kentucky Derby runner-up was one of Display’s progeny, Discovery.

Impressive, the Belmont Stakes of 2000

• Odds of 19-1
• Pat Day is the jockey for this race.
• Bob and Beverly Lewis are the owners.

The bottom line is that Commendable’s time as a racehorse was incredibly brief. During his short career, he competed in only 12 races, winning twice, including the 2000 Belmont Stakes.

Commendable was an underdog in the Belmont Stakes for a reason. He finished 17th out of 19 horses in the Kentucky Derby, and his owners didn’t even run him in the Preakness Stakes before the Triple Crown contests.

Kentucky-bred horse Commendable spent five years in a stud in the US before moving to Korea and remaining there until his death from colic in 2014.

Preakness Stakes at Coventry, 1925

• There are 21-1 odds of winning.
• Clarence Kummer is the jockey.
• Gifford A. Cochran is the owner.

Coventry was trained by the legendary Bill Duke, who himself only ran in five races and won one, the 1925 Preakness Stakes, as a 21-1 outsider.

For the past 50 years, Coventry was the Preakness’s most significant long shot winner until Master Derby in 1975. After his next race, his body began to fail him, and he retired to stud, where he had limited success.

In 1982, Gato Del Sol was released. The Kentucky Derby

• There are 21-1 odds of winning. /
• Eddie Delahoussaye is the rider.
• Hancock and Peters, Inc.

Ultimately, Gato Del Sol was one of our most diminutive favorite horses because his father, Cougar, was a Chilean racehorse.

Where does Gato Del Sol fall short for us? To focus on the Belmont Stakes, where Gato finished second, Gato’s trainers chose to skip the Preakness Stakes and focus on the Kentucky Derby.

I can’t think of anything worse than getting a chance to make history and then deciding not to take it. Cowards.

Animal Kingdom, the Kentucky Derby in 2011

• There are 21-1 odds of winning.
• John Velazquez is the rider.
• Incorporated by Team Valor International

After pulling off a stunning upset in 2011 in the Kentucky Derby, Animal Kingdom finished second in the Preakness Stakes, putting him within striking distance of a Triple Crown attempt.

Following his 3-year-old season, injuries cut Animal Kingdom’s career short, but he recovered to become the only 5-year-old to win a Grade 1 event.

Master Derby, Preakness Stakes, 1975

• 23-1 are the odds against it happening.
• Darrell McHargue is the rider.
• Incorporated: Golden Chance Farms.

When it comes down to it, Master Derby should have won the Preakness Stakes without fanfare. Two wins as a 2-year-old and fourth place in the Kentucky Derby had earned him a reputation as one of the best horses in the world.

At his core, Master Derby was a victorious individual. Three more victories followed in 1976, including the Preakness.

The 2011 Belmont Stakes winner, Ruler on Ice

• A 25-1 shot.
• Jose Valdivia Jr. is the jockey.
• George and Lori Hall are the owners.

He performed best when the track wasn’t moving. Muddy tracks have been the setting for two of his three career victories.

At the Belmont Stakes in 2011, Ruler on Ice’s most significant victory was in the slop. Ruler entered the Kentucky Derby and Preakness Stakes as a 25-1 underdog, partly because he had not participated in either of the previous two Triple Crown races.

As a gelding — a horse who has been castrated — Ruler on Ice was one of the most unusual Triple Crown victors.

Kentucky Derby, 1918: Exterminator

• The odds are 29-1 against.
• Willie Knapp rode the horse.
• Willis Sharpe Kilmer is the proprietor.

In the end, Exterminator was not his family’s only Kentucky Derby champion. Donerail, Donerail’s older brother, won the Kentucky Derby in 1913. But I’ll get to him in a minute.

Right before his 3-year-old season, owner Willis Sharpe Kilmer purchased Exterminator as a “workhorse” to keep his most OK horse, Sun Briar, ready for competition. To Kilmer’s dismay, Exterminator was routinely referred to as such. He referred to him as “that goat.”

After that, you can probably guess what transpired. Kilmer reluctantly ran Exterminator after Sun Briar suffered a ringbone injury just days before the 1918 Kentucky Derby. Kilmer ran him till he was nine years old as a reward.

Exterminator was five years older than Kilmer when he died in 1945 at 30, an unusual turn of events.

1967 Kentucky Derby Champion: Proud Clarion

• 30-1 are the odds.
• Bob Ussery is the rider.
• Darby Dan Farm is the business owner.

As a 2-year-old, Proud Clarion could only come third in a handful of small sprints. After finishing second in the Blue Grass Stakes before the Kentucky Derby, 30-1 odds seemed like a long shot, but he showed enough promise to warrant the bet.

In the wake of his Kentucky Derby victory, Proud Clarion finished third in the Preakness and third in the Belmont Stakes.

The 1999 Kentucky Derby winner, charismatic

• Odds of 31-1
• Chris Antley is the rider.
• Bob and Beverly Lewis are the owners.

In the end, Charismatic stands out from the others since he has won the Triple Crown on many occasions.

As a 31-1 upset winner in the Kentucky Derby in 1999, Charismatic followed that up with a victory in the Preakness Stakes, giving him a shot at winning the Triple Crown.

Charismatic’s broken leg was memorably cradled in the hands of jockey Chris Antley when the horse was removed from the lead at the Belmont Stakes.

Apolo, the 1882 Kentucky Derby.

• The odds are 32-1.
• BABE HURD, the jockey
• Morris and Patton are the owners.

As a result: It has been 140 years since Apollo, a 32-1 outsider, won the Kentucky Derby in 1882.

It’s worth noting that Apollo never competed in a race as a 2-year-old. He was the first Kentucky Derby winner to win the Preakness Stakes before Justified in 2018.

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

Racehorse Gallahadion, 40th Kentucky Derby

• 35 to 1 are the odds.
• Carroll Bierman is the rider.
• Milky Way Farm is the farm’s owner.

Overall, Gallahadion was one of two grandsons of Reight Count, the 1928 Kentucky Derby winner, to win a Triple Crown race.

Gallahadion was the realization of a long-held racing fantasy for a very wealthy woman. In the years running up to the 1940 Kentucky Derby, Ethel V. Mars, heir to the Mars candy fortune, reportedly spent $500,000 on eight horses.

It’s too bad that Mars wasn’t present when one of her horses won the Kentucky Derby. She had a cold and was unable to go out.

The Belmont Stakes, 1971: Pass Catcher

• 35 to 1 are the odds.
• Walter Blum is the jockey for this race.
• October House Farm is the owner.

Bottom line: Canonero II, the Venezuelan colt who had won the Kentucky Derby and the Preakness Stakes, was the favorite to win the Belmont Stakes and bring the Triple Crown back to Venezuela. At 35-1 odds, Pass Catcher played spoiler in front of a record audience of 80,000 spectators.

Walter Blum, the jockey who rode Pass Catcher to win, claimed that he dropped his whip at the eighth pole but still rode the horse to victory.

Stakes winner Birdstone from the 2004 Belmont

• Odds of 36-1
• Edgar Prado is the rider for this race.
• Marylou Whitney Stables is the business’s owner.

Overall, Birdstone possesses one of the most impressive pedigrees of the horses featured in this article. Grindstone, the 1996 Kentucky Derby winner, was the damsire, and Unbridled, the sire, of Grindstone.

In 2004, Birdstone won the Belmont Stakes, where Smarty Jones was attempting to capture the Triple Crown, but he finished second to Birdstone in the last race.

Since he retired from racing, Birdstone has sired numerous notable champions, including Mine That Bird (2009), the Kentucky Derby winner, and Summer Bird (2009), the Belmont Stakes winner.

In the 2008 Belmont Stakes, Da’Tara finished third.

• The chances are 38-1.
• Alan Garcia is the rider.
• Robert V. LaPenta is the owner.

Ultimately, Big Brown had his sights set on the Triple Crown after victories in the Kentucky Derby and the Preakness Stakes, but Da’Tara ruined his plans for the Triple Crown.

One fascinating fact about Da’Tara is that his victory at the Belmont was both his only major victory and the last of his career. In 2011, the horse was put out to stud in Florida and eventually transferred to a farm in Venezuela for stud.

The year 2005: Giacomo The Kentucky Derby

• A 50-1 shot
• Mike Smith is the rider.
• Jerry and Ann Moss are the owners.

Giacomo, the horse, owned by A&M Records co-founder Jerry Moss and named after the son of artist Sting, was an oddity at the 2005 Kentucky Derby.

At Churchill Downs, Giacomo proved that he was more than just the bizarre facts he had been known for. Giacomo was hampered by breathing issues at the Preakness Stakes and the Belmont Stakes, where he finished third and eighth, respectively.

Giacomo was retired to stud after finishing fourth in the Breeders’ Cup Classic in 2006.

Miner’s Delight: The Kentucky Derby of 2009

• A 50-1 shot.
• Calvin Borel is the rider.
• Double Eagle Ranch is the owner.

Mine That Bird pulled off a surprising upset at the 2009 Kentucky Derby, launching off an atypical Triple Crown run that year — first at the Kentucky Derby, second at the Preakness Stakes and third at the Belmont Stakes — 2009.

By employing the “ride the rail” tactic, Mine That Bird made up an incredible amount of ground at the Kentucky Derby. NBC commentator Tom Durkin missed noticing him at first.

When Birdstone, a 36-1 longshot, triumphed in the Belmont Stakes in 2004, Mine That Bird’s father was bred.

The 1980 Belmont Stakes at Temperence Hill in New York City

• Odds are 53-1 in favor of winning.
• Eddie Maple is the rider.
• Loblolly Stable is the owner.

Temperance Hill’s odds of winning the Belmont Stakes in 1980 were astounding. He’d already won two Kentucky Derby prep races, the Rebel Stakes and the Arkansas Derby, before the Kentucky Derby.

As a 3-year-old, Temperence defeated Kentucky Derby winner Genuine Risk and Preakness champion Codex at Belmont. When he was sent up to stud in 1981, he produced three international champions, 39 stakes winners, and 433 winners totaling $26.5 million in earnings.

In 2003, Temperence Hill died.