Kentucky Derby History: Upset Winners and Unexpected Losers

by TerryMcNamee

Favourites don't have a great record in the Kentucky Derby. Usually they do place in the top five, but sometimes they are blown away by a horse no one expected to win.

By Terry McNamee © 2013

Certainly no one but the people who knew him best thought the little gelding Mine That Bird would win the 2009 Derby. In fact, he was at even longer odds than another gelding named Exterminator who destroyed a quality field in 1917. But these are not the only surprise winners of one of the most coveted racing trophies in the United States. Here are some of the upset winners who shocked everyone, sometimes even their owners, by bringing home a blanket of red roses on the first Saturday in May, and some of the “dead cert” favourites who lost.

Kentucky Derby Longshot Winners

To date, the two longest shots ever to win the Kentucky Derby since its first running in 1875 are Donerail in 1913 and Mine That Bird in 2009. Both paid more than $100 to win.

Donerail wins the Derby in 1913
Donerail wins the Derby in 1913
Wikimedia Commons

Donerail, 1913

Donerail remains the longest shot ever to win the Derby, going off at 91-1. The son of *McGee out of Algie M, by Hanover, paid a whopping $184.90 to win. His rider, Roscoe “The Golden Goose” Goose, was riding in his first Derby, and it would be his only win in three tries. Donerail won and placed in several other stakes at ages three and four.

Mine That Bird, 2009

A gelded son of Birdstone out of Mining My Own, by Smart Strike, Mine That Bird had been a champion in Canada at two, with three stakes wins under his belt. But when he was sold and then sent to an unknown New Mexico trainer named Chip Woolley, he fell right off the radar. Only his previous connections in Canada, his new owner and the people in the Woolley barn knew what the Bird was capable of. His Derby run up the rail with Calvin Borel aboard remains one of the most memorable Derbies ever. He paid $103.20 to win.

Not only did he win, Mine That Bird ran the last quarter-mile in a shockingly fast 23-1/5 seconds in the mud to defeat Pioneerof The Nile and Musket Man. Even Secretariat needed a fast track to post that kind of speed. He went on to place a very close second in the Preakness, gaining with every stride on the winning Rachel Alexandra, and third in the Belmont where he received a less than perfect ride from Borel.

Sadly, his Derby win was the Bird's last win. He was transferred to trainer D. Wayne Lukas, who repeatedly ran him in big stakes without giving him a chance to regain his confidence in a lesser race. He was retired to his owner's New Mexico farm at the end of his 4-year-old season with winnings of nearly $2.3-million. Meanwhile, Pioneerof The Nile was injured in July 2009 and retired to stud. Musket Man raced well at four before retiring to stud in 2011.

Mine That Bird at Woodbine, 2008
Mine That Bird at Woodbine, 2008
Michael Burns/Woodbine Entertainment
Exterminator in 1922
Exterminator in 1922
Wikimedia Commons

Giacomo, 2005

Giacomo was another horse ignored by bettors on Derby day. The grey son of Holy Bull—Set Them Free, by Great Above defeated Closing Argument and favourite Afleet Alex. Future star Flower Alley was 9th. Giacomo paid $102.50 to win, which at the time was the second-highest Derby payoff ever. Afleet Alex was named Champion Three-Year-old that year. Giacomo won or placed in three graded stakes at four, then was retired to stud in 2006, but did not attract the best mares and has not been considered very successful as a stallion to date. However, that could change, as he already has four stakes winners in 2013.

Exterminator, 1918

The rangy gelding known as “Old Bones” was bought as a work mate for the 1917 Juvenile Champion, Sun Briar, but when the stable star was injured, owner W.S. Kilmer reluctantly agreed to run Exterminator in the Derby. The gelding defeated a field of eight on a muddy track and paid $61.20 to win. He was the second Derby winner by *McGee, and was out of Fair Empress, by Jim Gore. Exterminator went on to become Horse of the Year in 1922 and Champion Handicap Horse three times. He won 50 of 100 lifetime starts at ages three, four and five, including a record 33 stakes, and finished worse than third only 16 times.

Dark Star, 1953

Everyone knew the great Native Dancer was certain to win the Triple Crown, but it was not to be. Native Dancer had a very troubled trip in the Derby, and, when he got a clear run, he just ran out of racetrack. Cain Hoy Stables' Dark Star got the win and became the only horse to finish in front of The Grey Ghost. Others finishing further back included good horses like Social Outcast, Curragh King and Ace Destroyer.

Dark Star, a son of Royal Gem II—Isolde, by Bull Dog, seriously injured a tendon while finishing fifth in the Preakness and had to be retired. At stud, he sired Canadian Horse of the Year Hidden Treasure, the good stakes winner My Dad George (second in the Derby and Preakness) and the dam of the great champion Youth. Overall, he sired 26 stakes winners from 266 foals to race.

Canonero II wins the Kentucky Derby
Canonero II wins the Kentucky Derby

Canonero II, 1971

Born with a crooked front leg, Canonero was sold to interests in Venezuela for just $1,200 as a yearling. When the son of *Pretendre—Dixieland, by Nantallah returned to Kentucky to run in the Derby, people said he was badly outclassed. But the colt pulled an amazing upset in the 20-horse field, defeating Jim French, Bold Reason, Eastern Fleet and Unconscious. He paid $19.40 to win as part of the six-horse mutual field.

Like Mine That Bird, Canonero closed from far back to win the Derby by open lengths, and was clearly the best that day.

But after the Derby, the front cover of Sports Illustrated that week stated, “Canonero Should Not Have Run.” He proved them wrong, winning the Preakness in track-record time. He was suffering from a foot infection when he placed fourth in the Belmont. He was named Champion 3-Year-old Colt for 1971 and went on to beat Riva Ridge in the Stymie Handicap at four. As a stallion, he did not get quality mares and had little opportunity to reproduce his brilliance, and was sent back to Venezuela.

Winning Colors, 1988

The big grey filly was one of the favourites, but was mostly a sentimental choice. After all, only two fillies had ever won the Run For the Roses, but she had already soundly trounced colts in the Santa Anita Derby. The daughter of Caro—All Rainbows, by Bold Hour defeated one of the strongest Derby fields in history, including Forty Niner, Risen Star, Proper Reality, Regal Classic and Seeking the Gold, winning by a neck. She followed up with a third place in the Preakness and lost the Breeders' Cup Distaff by the narrowest of margins to Personal Ensign. She was named Champion Three-Year-Old Filly of 1988. Winning Colors raced at four but won just two of seven starts. Bred to the best stallions available, none of her ten foals were particularly good, although one, Golden Colors, had modest success in Japan.

Charismatic, 1999

Charismatic, trained by D. Wayne Lukas, was not expected to even earn a cheque in the Kentucky Derby. When the son of Summer Squall— Bali Babe, by Drone defeated Menifee and Cat Thief, he paid $64.60 to win. He then won the Preakness, and looked ready for a Tripled Crown. Sadly, in the Belmont, the horse broke down as he crossed the finish line in third place. Jockey Chris Antley saved the horse's life by bringing him to a stop, jumping off and grabbing the injured leg so the horse was putting no weight on it. Charismatic never raced again, but survived surgery to repair his leg and went on to a successful stud career in Japan. Finishing ninth was Lemon Drop Kid, a future good sire.

Beaten Favourites in the Kentucky Derby

Some favourites simply ran a bad race in the Kentucky Derby, then came back to excel later in the season. Some were just edged out, some had a dreadful trip and at least one lost when a jockey made a mistake. Here are just a few of the most unexpected losers in the Run for the Roses.

Native Dancer, whose only loss in 22 starts was the Kentucky Derby.
Native Dancer, whose only loss in 22 starts was the Kentucky Derby.
Wikimedia Commons

Native Dancer, 1953

No one thought that Native Dancer, the Grey Ghost of Sagamore, could lose the Derby. But a bad ride by Eric Guerin and getting bumped on the first turn and again on the backstretch left the son of Polynesian—Geisha, by Discovery 10 lengths back of the leaders. He made up a huge amount of ground to place second to Dark Star. It would be his only loss in 22 career starts. He went on to win the Preakness and Belmont and was named Champion 3-Year-Old Colt despite the loss, and became a great sire.

Arazi, 1992

A Breeders' Cup Champion at two, Arazi was considered such a big favourite in the Derby that the amount of money wagered on him to win was equal to the win wagers on all the other 17 entries combined. At the quarter pole, he made a huge rush into third place and looked like a sure winner, only to tire and fade to eighth. An 18-1 longshot named Lil E. Tee was the winner. Arazi did race a few more times, but was unable to recapture the brilliance he had shown at two. As a stallion, the son of Blushing Groom—Danseur Fabuleaux, by Northern Dancer stood in England, Kentucky, Japan, Australia, Switzerland and again in Kentucky. He was a decent sire, but proved to be much better as a sire of good broodmares. The winner, Lil E. Tee, was not successful at stud.

Gallant Man, 1957

The British-bred Gallant Man should have been a clear winner of the 1957 Derby, and would have been if jockey Bill Shoemaker had not misjudged the finish fine and stood up in his stirrups. A moment later, he realized his error and sat down to ride again, but Gallant Man had slowed just enough to let Iron Liege catch him right at the wire. Iron Liege was a decent horse, but definitely was not nearly as good as Gallant Man.

Gallant Man
Gallant Man

Gallant Man went on to win the Belmont Stakes by eight lengths, plus the Travers and the Jockey Club Gold Cup. He also won three major stakes the following year. Gallant Man, by Migoli—Majideh, by Mahmoud, was barely over 15 hands, yet succeeded while racing against two of the best of the decade in Bold Ruler and Round Table. He sired 52 stakes winners and was broodmare sire of champions Genuine Risk and Gallant Bloom. He lived to be 34 years old.

Holy Bull, 1994

A grey son of Great Above—Sharon Brown, by Minnesota Mac, Holy Bull was unbeaten at two and went into the Derby as the favourite, but finished a dismal twelfth in a field of fourteen. He skipped the next two Triple Crown races, but went on later that year to win several major stakes over older horses, including six straight wins, and was named Champion Three-Year-Old and Horse of the Year. He went on to become a very important sire. The Derby winner, Go For Gin, never won another race despite making nine more starts, but did finish second in both the Preakness and Belmont, both to Tabasco Cat (sixth in the Derby) and placed in three more stakes. Unlike Holy Bull, Go For Gin was only a moderate success at stud.

Skip Away, 1996

The grey Skip Trial son Skip Away, America's champion Three-Year-old in 1996, ran an unexpectedly bad race in the Derby to finish twelfth, well back of winner Grindstone. He redeemed himself by placing second in both the Preakness and Belmont and winning the Haskell Invitational, the Jockey Club Gold Cup and the Woodbine Million. He went on to become champion handicap horse the next two years and Horse of the Year in 1998. He was never popular as a sire, despite a record of 21 stakes winners from just 489 foals.

Bodemeister and Union Rags, 2012

In a packed field of 20, including such good horses as Dullahan, Hansen, Gemologist and other stakes winners, the two standouts were two-year-old champion Union Rags, trained by Michael Matz (who had trained the ill-fated Derby winner Barbaro), and Bodemeister, whose trainer Bob Baffert had just survived a near-fatal heart attack. No one expected the Canadian-owned chestnut I'll Have Another, a 15-1 longshot, to catch Bodemeister with just 150 yards to go and fly past him him to win. Dullahan was third. Union Rags had a nightmare trip and finished seventh.

In the Preakness, it happened again, with favourite Bodemeister having to settle for second to I'll Have Another. Union Rags sat this one out, but came back to win the Belmont after I'll Have Another was scratched due to a tendon injury. Bodemeister, tired of being second, skipped the Belmont. I'll Have Another went to stud in Japan. Union Rags (Dixie Union—Tempo, by Gone West) was injured in July 2012 and retired to stud in Kentucky. Bodemeister (Empire Maker—Untouched Talent, by Storm Cat) was diagnosed with a shoulder injury in August 2012 and retired to stud in Kentucky.

These are just a few of the many stories of amazing Kentucky Derby surprise winners and of great horses who, as betting favourites, failed to win this prestigious race. But win or lose, they are all part of the history of the Run For the Roses.

Additional Reading

There are many wonderful books about the Kentucky Derby and the horses that raced in them. Here are a few titles that you might enjoy.

Two Minutes to Glory: The Official History of the Kentucky Derby

Take a front row seat at "the Run for the Roses" with the first comprehensive history of the Kentucky Derby. From mint juleps to the garland of roses, to weeping men and women i...

View on Amazon

Remembering the Derby

"Followers of the Sport of Kings will find the book irresistible." -Publishers Weekly Jim Bolus's Kentucky Derby Stories was called "a Derby delight," "entertaining," and "a win...

View on Amazon

Greatest Kentucky Derby Upsets

From Elwood in 1904 to Giacomo in 2005, upset winners of the Kentucky Derby have contributed to the race's incredible lore. This collection explores the tales of some of the Der...

View on Amazon

The Longest Shot: Lil E. Tee and the Kentucky Derby

" On the first Saturday in May every year in Louisville, Kentucky, shortly after 5:30 PM, a new horse attains racing immortality. The Kentucky Derby is like no other race, and i...

View on Amazon

Updated: 04/29/2013, TerryMcNamee
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TerryMcNamee on 03/13/2024

I think he did not get quality mares because his pedigree was not as popular as those of other stallions at that time. As well, he was at stud at King Ranch in Texas, not in Kentucky, where the best mares were sent for breeding. According to Pedigree Query, he sired fewer than 80 registered foals.

DerdriuMarriner on 03/12/2024

The third paragraph to the sixth long-shot, Canonero II, 1971, advises us that "As a stallion, he did not get quality mares and had little opportunity to reproduce his brilliance, and was sent back to Venezuela."

Is it known why Canonero II lacked "quality mares"?

Ann on 04/29/2013

That was great to read! Especially with the Derby coming up for this year!

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