Kentucky Derby Upsets

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

The memories made with each Run For The Roses 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 Derby’s usually involve a heavily-favored horse Winning and thus etching his (or her) name into the history books, there have been some upsets for the ages as well.

Looking back through the Kentucky Derby’s history there are many upsets that stand out for different reasons.

For the sake of brevity we’ve chosen two BIG Derby upsets from the 21st century. See if you recall these monumental Victories.

GIACOMO, 2005 It was perhaps THE textbook example of that old axiom pace makes the race. Derby 131 featured two solid favorites in Wood Memorial Winner BELLAMY ROAD (5-2) and Arkansas Derby Winner AFLEET ALEX (9-2) but otherwise was a crapshoot in terms of handicapping.

The race unfolded like something from a Quarter Horse contest 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 72-1 shot, dueled with AFLEET ALEX in the final sixteenth of a mile, but then both were passed on the outside by a grinding 50-1 shot named GIACOMO, who entered the Kentucky Derby with one win from seven starts and had previously finished 4th in the Santa Anita Derby.

GIACOMO Won by a half-length over CLOSING ARGUMENT, AFLEET ALEX was 3rd, 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 3rd in the Preakness, 7th in the Belmont, and Won one more stakes race in 2006 before retiring.



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, maybe after this edition they did.

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.

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 50-1.

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 PIONEER OF THE NILE on the way to a 6 ¾-length Victory.

Announcer Tom Durkin’s incredulous race call accurately expressed the sentiments of a chorus of racing fans and still brings smiles today. Durkin did not see MINE THAT BIRD coming through on the rail and did not give him a call until he was several lengths ahead.

MINE THAT BIRD ran valiantly in the Preakness but could not defeat eventual 2009 Horse of the Year RACHEL ALEXANDRA (Borel was aboard the filly- an easy decision), and he finished 3rd 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.

The 2022 Kentucky Derby is May 7th.

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