Ten Unforgettable Kentucky Derby Upsets



The Kentucky Derby Offered by Woodford Reserve just isn’t solely probably the most anticipated, most watched Thoroughbred race on the earth however a necessary a part of American sports activities tradition.

Recollections are made with every run for the roses that over the passage of time turn into legend, not solely to day-to-day followers of horse racing however to most of the people.

Whereas probably the most memorable Kentucky Derbys often contain a heavily-favored horse profitable and thus etching his (or, thrice, her) title into the historical past books, there have been some upsets for the ages as effectively.

Two years in the past, Wealthy Strike didn’t initially qualify for the 20-horse Kentucky Derby however acquired a spot the day earlier than the race after one other horse was withdrawn, and subsequently he pulled probably the most stunning upsets within the 148th version of the race at Churchill Downs

Trying again via the Derby’s historical past, these 10 (introduced in historic order) stand out for various causes. Some contain an unheralded longshot profitable the hearts of horse racing followers in a aggressive yr the place there was no standout. Others occurred when an unbelievable horse upset a clear-cut favourite, leaving handicappers and followers bewildered and some fortunate bettors thrilled. With out additional adieu …


1) Apollo, 1882

Apollo’s title was entrance and heart within the dialogue concerning the 2018 Kentucky Derby, as chatter concerning the enduring “curse of Apollo” was put to relaxation when Justify grew to become the primary horse in 136 years to win the Derby with out racing as a 2-year-old (Mage achieved the identical feat final yr).

However the gelding’s long-ago win additionally qualifies as arguably the primary vital upset in Kentucky Derby historical past, albeit a modest one in contrast with others on this checklist. He defeated a horse named Runnymede, named after the Central Kentucky farm the place he was bred (which nonetheless exists immediately) and campaigned by the well-known Dwyer brothers, who had gained the prior yr’s Kentucky Derby with Corridor of Famer Hindoo, one of many all-time greats.

Apollo was guess at 10-1 odds via bookmakers, whereas Runnymede was given 4-5 odds. The eighth Kentucky Derby chart reads that Runnymede “appeared just like the winner till Apollo began a cyclonic rush an eighth of a mile from residence.” Apollo’s closing margin within the 1 ½-mile Derby was a half-length, giving him the second of 24 profession wins and a spot in Kentucky Derby historical past that, certainly, did endure for almost a century and a half earlier than Justify got here alongside.


2) Donerail, 1913

100 and eleven years later, Donerail nonetheless holds the Kentucky Derby document because the highest-priced winner at 91.45-1 odds. The colt, owned, bred, and educated by Thomas P. Hayes, capitalized on a swift early tempo and rallied from fifth on the high of the stretch to win by a half-length. His lengthy odds, set via what was then a comparatively new pari-mutuel system of betting, have been the results of heavy wagering on two favorites, runner-up Ten Level and fourth-place finisher Basis.

Donerail’s jockey, Roscoe Goose, grew to become an influential determine as a coach in Kentucky’s horse racing world within the years after the unbelievable Derby win, and in addition 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, however that’s solely a small a part of Exterminator’s story. Simply one of the best racehorse on this checklist, the gelding competed as much as his 9-year-old season in 1924 and was famend for his sturdiness and flexibility, profitable precisely half of 100 profession begins and a document 33 (or 34, the quantity remains to be a matter of dispute) stakes races.

His one-length Kentucky Derby win got here after a 9 ½-month layoff, and he began within the Derby solely as a result of he outworked his coaching mate main as much as the race. The upset jump-started a profession that made him a nationwide fan favourite, particularly as he grew older and saved profitable. Learn extra concerning the beloved “Previous Bones” in J. Keeler Johnson’s Legends profile for America’s Finest Racing.


4) Gallahadion, 1940

The 1940 Derby featured a heavy favourite in Bimelech, who was the champion 2-year-old in 1939 and was the fifth foal produced by La Troienne – probably the most vital basis mares in Thoroughbred breeding throughout the 20th century. Col. Edward R. Bradley’s Bimelech was despatched off at 2-5 odds within the Kentucky Derby, whereas Gallahadion, owned by the Milky Approach Farm of Ethel Mars (of Mars Sweet riches), was a 35.20-1 longshot.

In probably the most stunning Derby ends in historical past, Gallahadion rushed up alongside the rail to overhaul Bimelech and win going away by 1 ½ lengths. Corridor of Famer Bimelech would go on to win each the Preakness Stakes and Belmont Stakes and be named champion 3-year-old, whereas Gallahadion completed third and fifth in these races.


5) Darkish Star, 1953

The 1953 Kentucky Derby ranks as an excellent greater upset than Gallahadion’s 1940 win – and arguably as the most important upset in Derby historical past. To set the stage: Harry Guggenheim’s Darkish Star gained one stakes as a 2-year-old after which captured the Derby Trial a mere 5 days earlier than 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 12 months in two out of three polls) from the yr earlier than.

What ensued as soon as the Derby beginning gate opened was a nightmarish journey for Native Dancer as he was roughed early and compelled to settle farther again than normal, which allowed Darkish Star to set an uncontested tempo. Native Dancer rallied swiftly via the stretch however got here up a head brief, giving 24.90-1 shot Darkish Star an historic victory. (Learn an in depth account of the 1953 Derby in America’s Finest Racing contributor Bob Ehalt’s profile of Native Dancer.)

Native Dancer would go on to win the Preakness as Darkish Star suffered a career-ending damage when ending fifth. The “Gray Ghost of Sagamore Farm” additionally gained the Belmont and was named champion 3-year-old colt – after which adopted up with a Horse of the 12 months season in 1954. He retired with a profession document of 22-21-1-0 and was inducted into the Racing Corridor of Fame in 1963, with the Kentucky Derby the one blemish on what is definitely one of many biggest résumés in Thoroughbred racing historical past.


6) Proud Clarion, 1967

The 93rd run for the roses introduced one other shocker to the sports activities world simply earlier than burgeoning hippies’ minds have been blown by the discharge of The Beatles’ “Sgt. Pepper’s Lonely Hearts Membership Band a month later. Damascus entered the Derby with six wins from eight begins, his most up-to-date a six-length runaway within the Wooden Memorial. Proud Clarion, however, had completed third as soon as in three begins at 2 and gained 4 minor races early in his 3-year-old season earlier than ending second within the Blue Grass Stakes.

However within the Kentucky Derby, the son of breed-shaping sire Hail to Purpose capitalized on a skillful trip by Bobby Ussery to navigate out and run down pacesetter Barbs Delight for a one-length win at 30.10-1 odds. Damascus additionally made a threatening transfer on the high of the lane below Invoice Shoemaker however hung late and settled for third because the 1.70-1 favourite.

Damascus would go on to submit dominant wins in each the Preakness and Belmont, whereas Proud Clarion completed 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 within the Woodward Stakes. That yr, he gained 12 of 16 races and was a cinch alternative as Horse of the 12 months and champion 3-year-old.

Proud Clarion’s Kentucky Derby win was the second in 5 years for John W. Galbreath’s venerable Darby Dan Farm in Lexington, following Chateaugay’s win in 1963.


7) Giacomo, 2005

Let’s bounce to the trendy period and recall the wild 2005 Derby, which, together with the 2022 run for the roses, exemplifies that outdated axiom: “tempo makes the race.” Derby 131 featured two strong favorites in Wooden Memorial winner Bellamy Street (2.60-1) and Arkansas Derby winner Afleet Alex (4.50-1) however in any other case was a crapshoot by way of handicapping. The race unfolded like one thing from the Ruidoso Downs Quarter Horse circuit early on, as Spanish Chestnut led the sphere via opening quarter-mile splits of :22.28 and :45.38. By the point the sphere turned for residence, there have been about 10 horses seemingly with an opportunity, however most of them have been already staggering.

Closing Argument, a 71.60-1 shot, dueled with Afleet Alex within the closing sixteenth of a mile, however then each have been handed on the surface by a grinding 50.30-1 shot named Giacomo, who entered the Kentucky Derby with one win from seven begins for Jerry and Ann Moss and had beforehand completed fourth within the Santa Anita Derby.

Giacomo gained by a half-length over Closing Argument, Afleet Alex was third, and the $1 superfecta paid a document $864,253.50. Afleet Alex would go on to win the Preakness after almost falling on the high of the stretch, after which dominate the Belmont. Giacomo completed third within the Preakness, seventh within the Belmont, and gained yet one more stakes race in 2006 earlier than retiring.


8) Mine That Hen, 2009

The 135th Derby holds a particular place within the coronary heart of many modern racing followers and even grizzled veterans of the Churchill Downs grandstand who suppose they’ve seen all of it. Effectively, after Mine That Hen’s win, possibly they’ve.

The storyline might haven’t been extra excellent. A bunch of unknown connections from New Mexico. A house-track rider within the midst of a career-best run who was driving a famous person filly within the Kentucky Oaks however wanted a Derby mount. And a modestly-accomplished gelding who, primarily based on all previous type, ought to have been working a few weeks earlier on Keeneland’s then-synthetic monitor.

There wasn’t a heavy favourite within the rain-soaked 2009 Derby, and definitely quite a lot of on-track attendees positioned a guess on Mine That Hen as a consequence of their love for jockey Calvin Borel, however he nonetheless went off at 50.60-1. The replay calls for repeat watching, simply to establish the come-from-the-clouds bay blur that sped via the far activate the within, after which darted out and again in once more on the high of the stretch hugging the “Bo-rail” earlier than taking pictures previous Pioneerof the Nile en path to a 6 ¾-length victory.

Tom Durkin’s incredulous race name precisely expressed the emotions of a refrain of racing followers and nonetheless brings smiles immediately. Mine That Hen ran valiantly within the Preakness however couldn’t defeat Oaks winner and eventual 2009 Horse of the 12 months Rachel Alexandra (with Borel staying aboard the filly, a straightforward choice), and he completed third within the Belmont after which misplaced seven races to shut out his profession. Nonetheless, his reputation as probably the most unpredictable and immediately beloved Kentucky Derby winners grew to become instantly obvious when he introduced the game of kings again to the duvet of Sports activities Illustrated after a five-year absence. It has endured within the years since, too, as evidenced by a the discharge of a 2014 characteristic movie about his win and Mine That Hen’s periodic visits to the Kentucky Derby Museum, together with this yr. In 2018, Calvin Borel spoke with ABR correspondent Jeff Lowe about his superb Derby win aboard Mine That Hen.


9) Nation Home, 2019

By means of 144 years of its historical past, just one Kentucky Derby winner had been disqualified, and that occurred days after the 1968 renewal when Dancer’s Picture was DQ’d as a consequence of a controversial drug violation (Ahead Go grew to become the 94th Derby winner).

A well-matched group of 3-year-olds headed into Derby 145 with no clear divisional chief, though an upstart colt named Most Safety acquired loads of consideration after he rose out of the maiden claiming ranks at Gulfstream Park to go undefeated via 4 begins with a runaway 3 ½-length win the Florida Derby.

Nation Home, however, had solely gained one in all six begins for Corridor of Fame coach Invoice Mott, who was searching for his first Kentucky Derby win, and arrived to Churchill off of a nonthreatening third within the Arkansas Derby.

What transpired on Might 4 set a brand new marker in Kentucky Derby historical past with ramifications which might be nonetheless making an influence on the game 5 years later (coupled within the minds of many with the 2021 Derby, which resulted within the second medication-related DQ in historical past). Most Safety, despatched off at 9-2 odds, used his customary pace to set the tempo on a sloppy monitor solely to be challenged by a number of horses via the far flip. His response to that strain on the five-sixteenths pole grew to become the Zapruder movie of Thoroughbred racing within the weeks to observe, studied endlessly by armchair stewards with conflicting axes to grind.

Did his wayward working trigger Conflict of Will, Lengthy Vary Toddy, and/or Bodexpress a putting? (Conflict of Will definitely had the strongest case.) Ought to a horse who was clearly one of the best on Derby day be taken down for actions that occurred earlier than the stretch run? These questions are nonetheless fodder for debate … however after an excruciating wait of greater than quarter-hour, 65.20-1 Nation Home was formally declared the beneficiary and made what was at the moment the second largest longshot to ever win the run for the roses. 


10) Wealthy Strike, 2022

There’s nobody round to argue whether or not Donerail’s win again in 1913 actually is the most important upset ever within the Kentucky Derby, even when parimutually talking he did produce the biggest payout within the document books. So let or not it’s unchallenged: what racing followers witnessed Might 7, 2022 is probably the most unlikely outcome within the almost 150-year historical past of America’s largest race.

What number of lucky flip of occasions wanted to happen simply to get Wealthy Strike into the Kentucky Derby beginning gate and provides him an opportunity to shock the world? In the event you suppose lengthy and exhausting sufficient, the primary domino fell when Churchill Downs Inc. purchased Turfway Park in 2019. Churchill subsequently raised the factors distribution considerably for Turfway’s Kentucky Derby prep, the Jeff Ruby Steaks, and additionally added the John Battaglia Memorial Stakes at Turfway as a Derby factors race, each in 2021.

One yr later, Wealthy Strike completed fourth within the Battaglia and third within the Jeff Ruby, and the collected 21 factors gave him simply sufficient to sit down first on the also-eligible checklist for Derby 148 with lower than 48 hours remaining earlier than the race. All it took after that was a) the connections of Ethereal Street deciding to withdraw that horse from the sphere, enabling Wealthy Strike to attract in; b) jockey Sonny Leon patiently positioning his horse close to the again of the sphere after angling him in to save lots of floor from the 20th submit place; c) Dubai-based sprinter Summer time Is Tomorrow main the pack via blazing early fractions, together with the quickest opening quarter-mile (:21.78) within the historical past of the race and a half-mile in :45.36; d) Leon navigating his mount via site visitors on the far flip and in early stretch with flawless precision as Wealthy Strike moved previous tiring foes, as displayed in aerial cam footage that’s been considered hundreds of thousands of occasions; and e) runner-up Epicenter and third-place Zandon tiring simply sufficient within the closing sixteenth of a mile whereas dueling one another to utterly miss the 80.80-1 shot rallying to their inside.

Proprietor Richard Dawson, coach Eric Reed, and jockey Leon have been all Derby first-timers, and so they appeared as shocked concerning the outcome because the hordes of followers watching in particular person, on TV and on their units. We’ve all actually turn into accustomed to upsets on the primary Saturday in Might… however nobody alive has ever seen something like what Wealthy Strike pulled off two years in the past. It’s a part of what makes the race so enjoyable, yr after yr.



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