Ten Unforgettable Kentucky Derby Upsets

Calvin Borel's rail-skimming ride aboard Mine That Bird in 2009 led to one of the biggest upsets in Kentucky Derby history. (Eclipse Sportswire)

The Kentucky Derby Presented by Woodford Reserve is not only the most anticipated, most watched Thoroughbred race in the world but an essential part of American sports culture.

Memories are made with each run for the roses that over the passage of time become legend, not only to day-to-day followers of horse racing but to the general public.

While the most memorable Kentucky Derbys usually involve a heavily-favored horse winning and thus etching his (or, three times, her) name into the history books, there have been some upsets for the ages as well.

Last year, Rich Strike failed to initially qualify for the 20-horse Kentucky Derby but received a spot the day before the race after another horse was withdrawn, and subsequently he pulled one of the most shocking upsets in the race’s 148-year history at Churchill Downs

Looking back through the Derby’s history, these 10 (presented in historical order) stand out for different reasons. Some involve an unheralded longshot winning the hearts of horse racing fans in a competitive year where there was no standout. Others occurred when an improbable horse upset a clear-cut favorite, leaving handicappers and fans bewildered and a few lucky bettors thrilled. Without further adieu …

1) Apollo, 1882

Apollo’s name was front and center in the discussion about the 2018 Kentucky Derby, as chatter about the enduring “curse of Apollo” was put to rest when Justify became the first horse in 136 years to win the Derby without racing as a 2-year-old.

But the gelding’s long-ago win also qualifies as arguably the first significant upset in Kentucky Derby history, albeit a modest one compared with others on this list. He defeated a horse named Runnymede, named after the Central Kentucky farm where he was bred (which still exists today) and campaigned by the famous Dwyer brothers, who had won the prior year’s Kentucky Derby with Hall of Famer Hindoo, one of the all-time greats.

Apollo was bet at 10-1 odds through bookmakers, while Runnymede was given 4-5 odds. The eighth Kentucky Derby chart reads that Runnymede “looked like the winner until Apollo started a cyclonic rush an eighth of a mile from home.” Apollo’s final margin in the 1 ½-mile Derby was a half-length, giving him the second of 24 career wins and a place in Kentucky Derby history that, indeed, did endure for nearly a century and a half before Justify came along.

1913 Derby winner Donerail (Wikimedia Commons)

2) Donerail, 1913

One hundred and nine years later, Donerail still holds the Kentucky Derby record as the highest-priced winner at 91.45-1 odds. The colt, owned, bred, and trained by Thomas P. Hayes, capitalized on a swift early pace and rallied from fifth at the top of the stretch to win by a half-length. His long odds, set through what was then a relatively new pari-mutuel system of betting, were the result of heavy wagering on two favorites, runner-up Ten Point and fourth-place finisher Foundation.

Donerail’s jockey, Roscoe Goose, became an influential figure as a trainer in Kentucky’s horse racing world in the years after the improbable Derby win, and also served as a mentor to such legendary riders as Charlie Kurtsinger and Eddie Arcaro.

3) Exterminator, 1918

He was a 29.60-1 winner of the Kentucky Derby, but that is only a small part of Exterminator’s story. Easily the best racehorse on this list, the gelding competed up to his 9-year-old season in 1924 and was renowned for his durability and versatility, winning exactly half of 100 career starts and a record 33 (or 34, the number is still a matter of dispute) stakes races.

His one-length Kentucky Derby win came after a 9 ½-month layoff, and he started in the Derby only because he outworked his training mate leading up to the race. The upset jump-started a career that made him a national fan favorite, especially as he grew older and kept winning. Read more about the beloved “Old Bones” in J. Keeler Johnson’s Legends profile for America’s Best Racing.

4) Gallahadion, 1940

The 1940 Derby featured a heavy favorite in Bimelech, who was the champion 2-year-old in 1939 and was the fifth foal produced by La Troienne – one of the most important foundation mares in Thoroughbred breeding during the 20th century. Col. Edward R. Bradley’s Bimelech was sent off at 2-5 odds in the Kentucky Derby, while Gallahadion, owned by the Milky Way Farm of Ethel Mars (of Mars Candy riches), was a 35.20-1 longshot.

In one of the most shocking Derby results in history, Gallahadion rushed up along the rail to overtake Bimelech and win going away by 1 ½ lengths. Hall of Famer Bimelech would go on to win both the Preakness Stakes and Belmont Stakes and be named champion 3-year-old, while Gallahadion finished third and fifth in those races.

5) Dark Star, 1953

The 1953 Kentucky Derby ranks as an even bigger upset than Gallahadion’s 1940 win – and arguably as the biggest upset in Derby history. To set the stage: Harry Guggenheim’s Dark Star won one stakes as a 2-year-old and then captured the Derby Trial a mere five days before the Kentucky Derby. Conversely, Alfred G. Vanderbilt’s Native Dancer entered the Derby with 11 consecutive wins (the shortest coming by 1 ¼ lengths) and already carrying champion 2-year-old honors (and Horse of the Year in two out of three polls) from the year before.

What ensued once the Derby starting gate opened was a nightmarish trip for Native Dancer as he was roughed early and forced to settle farther back than usual, which allowed Dark Star to set an uncontested pace. Native Dancer rallied swiftly through the stretch but came up a head short, giving 24.90-1 shot Dark Star a historic victory. (Read a detailed account of the 1953 Derby in America’s Best Racing contributor Bob Ehalt’s Legends profile of Native Dancer.)

Native Dancer would go on to win the Preakness as Dark Star suffered a career-ending injury when finishing fifth. The “Grey Ghost of Sagamore Farm” also won the Belmont and was named champion 3-year-old colt – and then followed up with a Horse of the Year season in 1954. He retired with a career record of 22-21-1-0 and was inducted into the Racing Hall of Fame in 1963, with the Kentucky Derby the only blemish on what is unquestionably one of the greatest résumés in Thoroughbred racing history.

6) Proud Clarion, 1967

The 93rd run for the roses brought another shocker to the sports world just before burgeoning hippies’ minds were blown by the release of The Beatles’ “Sgt. Pepper’s Lonely Hearts Club Band a month later. Damascus entered the Derby with six wins from eight starts, his most recent a six-length runaway in the Wood Memorial. Proud Clarion, on the other hand, had finished third once in three starts at two and won four minor races early in his 3-year-old season before finishing second in the Blue Grass Stakes.

But in the Kentucky Derby, the son of breed-shaping sire Hail to Reason capitalized on a skillful ride by Bobby Ussery to navigate out and run down pacesetter Barbs Delight for a one-length win at 30.10-1 odds. Damascus also made a threatening move at the top of the lane under Bill Shoemaker but hung late and settled for third as the 1.70-1 favorite.

Damascus would go on to post dominant wins in both the Preakness and Belmont, while Proud Clarion finished third and fourth, respectively. Then Damascus went on to win the Travers Stakes by 22 lengths and defeat Buckpasser and Dr. Fager by 10 lengths in the Woodward Stakes. That year, he won 12 of 16 races and was a cinch choice as Horse of the Year and champion 3-year-old.

Proud Clarion’s Kentucky Derby win was the second in five years for John W. Galbreath’s venerable Darby Dan Farm in Lexington, following Chateaugay’s win in 1963.

7) Giacomo, 2005

Let’s jump to the modern era and recall the wild 2005 Derby, which, along with last year’s run for the roses, exemplifies that old axiom: “pace makes the race.” Derby 131 featured two solid favorites in Wood Memorial winner Bellamy Road (2.60-1) and Arkansas Derby winner Afleet Alex (4.50-1) but otherwise was a crapshoot in terms of handicapping. The race unfolded like something from the Ruidoso Downs Quarter Horse circuit early on, as Spanish Chestnut led the field through opening quarter-mile splits of :22.28 and :45.38. By the time the field turned for home, there were about 10 horses seemingly with a chance, but most of them were already staggering.

Closing Argument, a 71.60-1 shot, dueled with Afleet Alex in the final sixteenth of a mile, but then both were passed on the outside by a grinding 50.30-1 shot named Giacomo, who entered the Kentucky Derby with one win from seven starts for Jerry and Ann Moss and had previously finished fourth in the Santa Anita Derby.

Giacomo won by a half-length over Closing Argument, Afleet Alex was third, and the $1 superfecta paid a record $864,253.50. Afleet Alex would go on to win the Preakness after nearly falling at the top of the stretch, and then dominate the Belmont. Giacomo finished third in the Preakness, seventh in the Belmont, and won one more stakes race in 2006 before retiring.

8) Mine That Bird, 2009

The 135th Derby holds a special place in the heart of many contemporary racing fans and even grizzled veterans of the Churchill Downs grandstand who think they’ve seen it all. Well, after Mine That Bird’s win, maybe they finally have.

The storyline could have not been more perfect. A bunch of unknown connections from New Mexico. A home-track rider in the midst of a career-best run who was riding a superstar filly in the Kentucky Oaks but needed a Derby mount. And a modestly-accomplished gelding who, based on all past form, should have been running a couple of weeks earlier on Keeneland’s then-synthetic track.

There wasn’t a heavy favorite in the rain-soaked 2009 Derby, and certainly more than a few on-track attendees placed a bet on Mine That Bird due to their love for jockey Calvin Borel, but he still went off at 50.60-1. The replay demands repeat watching, just to identify the come-from-the-clouds bay blur that sped through the far turn on the inside, and then darted out and back in again at the top of the stretch hugging the “Bo-rail” before shooting past Pioneerof the Nile en route to a 6 ¾-length victory.

Tom Durkin’s incredulous race call accurately expressed the sentiments of a chorus of racing fans and still brings smiles today. Mine That Bird ran valiantly in the Preakness but could not defeat eventual 2009 Horse of the Year Rachel Alexandra (with Borel aboard the filly, an easy decision), and he finished third in the Belmont and then lost seven races to close out his career. Still, his popularity as one of the most unpredictable and instantly beloved Kentucky Derby winners became immediately apparent when he brought the sport of kings back to the cover of Sports Illustrated after a five-year absence. It has endured in the 13 years since, too, as evidenced by the 2014 feature film “50 to 1." In 2018, Calvin Borel spoke with ABR correspondent Jeff Lowe about his amazing Derby win aboard Mine That Bird.

9) Country House, 2019

Through 144 years of its history, only one Kentucky Derby winner had been disqualified, and that occurred days after the 1968 renewal when Dancer’s Image was DQ’d due to a controversial drug violation (Forward Pass became the 94th Derby winner).

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A well-matched group of 3-year-olds headed into Derby 145 with no clear divisional leader, although an upstart colt named Maximum Security received a lot of attention after he rose out of the maiden claiming ranks at Gulfstream Park to go undefeated through four starts with a runaway 3 ½-length win the Florida Derby.

Country House, on the other hand, had only won one of six starts for Hall of Fame trainer Bill Mott, who was seeking his first Kentucky Derby win, and arrived to Churchill off of a nonthreatening third in the Arkansas Derby.

What transpired on May 4 set a new marker in Kentucky Derby history with ramifications that are still making an impact on the sport four years later (coupled in the minds of many with the 2021 Derby, which resulted in the second medication-related DQ in history). Maximum Security, sent off at 9-2 odds, used his customary speed to set the pace on a sloppy track only to be challenged by several horses through the far turn. His response to that pressure at the five-sixteenths pole became the Zapruder film of Thoroughbred racing in the weeks to follow, studied endlessly by armchair stewards with conflicting axes to grind.

Did his wayward running cause War of Will, Long Range Toddy, and/or Bodexpress a placing? (War of Will certainly had the strongest case.) Should a horse who was clearly the best on Derby day be taken down for actions that occurred before the stretch run? These questions are still fodder for debate … but after an excruciating wait of more than 15 minutes, 65.20-1 Country House was officially declared the beneficiary and made the second biggest longshot to ever win the run for the roses. 

10) Rich Strike, 2022

There’s no one around to argue whether Donerail’s win back in 1913 truly is the biggest upset ever in the Kentucky Derby, even if parimutually speaking he did produce the largest payout in the record books. So let it be unchallenged: what racing fans witnessed May 7 of last year is the most unlikely result in the nearly 150-year history of America’s biggest race.

How many fortunate turn of events needed to occur just to get Rich Strike into the Kentucky Derby starting gate and give him a chance to shock the world? If you think long and hard enough, the first domino fell when Churchill Downs Inc. bought Turfway Park in 2019. Churchill subsequently raised the points distribution significantly for Turfway’s Kentucky Derby prep, the Jeff Ruby Steaks, and also added the John Battaglia Memorial Stakes at Turfway as a Derby points race, both in 2021.

One year later, Rich Strike finished fourth in the Battaglia and third in the Jeff Ruby, and the accumulated 21 points gave him just enough to sit first on the also-eligible list for Derby 148 with less than 48 hours remaining before the race. All it took after that was a) the connections of Ethereal Road deciding to withdraw that horse from the field, enabling Rich Strike to draw in; b) jockey Sonny Leon patiently positioning his horse near the back of the field after angling him in to save ground from the 20th post position; c) Dubai-based sprinter Summer Is Tomorrow leading the pack through blazing early fractions, including the fastest opening quarter-mile (:21.78) in the history of the race and a half-mile in :45.36; d) Leon navigating his mount through traffic on the far turn and in early stretch with flawless precision as Rich Strike moved past tiring foes, as displayed in aerial cam footage that’s been viewed millions of times; and e) runner-up Epicenter and third-place Zandon tiring just enough in the final sixteenth of a mile while dueling each other to completely miss the 80.80-1 shot rallying to their inside.

Owner Richard Dawson, trainer Eric Reed, and jockey Leon were all Derby first-timers, and they seemed as shocked about the result as the hordes of fans watching in person, on TV and on their devices. We’ve all certainly become accustomed to upsets on the first Saturday in May… but no one alive has ever seen anything like what Rich Strike pulled off a year ago. It’s part of what makes the race so fun, year after year.

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