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What are the biggest upsets in Kentucky Derby history?

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Jerry Bailey and Randy Moss break down the 2023 Blue Grass Stakes from Keeneland, where Tapit Trice rode a much-improved beginning of the race to a victory over Verifying.

As the gates open on Derby Day, only one things remains certain — nothing is certain. The Kentucky Derby is home to some of the biggest upsets in sports history, turning underdogs in champions and dreams into realities.

The 149th Run for the Roses will take place on Saturday, May 6 at Churchill Downs in Louisville, Kentucky, setting the stage for another Thoroughbred to go down in history.

As you prepare to witness the most exciting two minutes in sports airing live on NBC and Peacock at 12 p.m. ET, see below to reminisce on some of the biggest upsets to take place at the Kentucky Derby.

RELATED: How to watch the 2023 Kentucky Derby: TV channel, live stream

Gato Del Sol (1982)

Entering the 1982 Run for the Roses, Gato del Sol was not on anyone’s radar as a potential Derby champion.

The horse, whose name translates from Spanish as Cat of the Sun, came into the race at odds of 21-1, not exactly a favorite for the roses. The start that Gato del Sol got off to was predictable, as the horse trailed in 19th place coming out of the first turn. Laser Light and Reinvested were just behind, at 18th and 17th, respectively.

These placings would soon be flipped upside down. The three Derby favorites lost steam after the first mile, opening the door for the bottom half to surge ahead. Gato Del Sol and Laser Light bursted forward, surpassing the leaders and fighting for first with only each other.

Gato Del Sol’s perserverance in the backstretch, however, was too much for Laser Light to overcome. The horse and his jockey, Eddie Delahoussaye, dominated in the race’s final moments, claiming a 2 1/2 length win. Delahoussaye, who was known for his remarkable faith in his horse throughout Gato Del Sol’s career, was not surprised by the success, knowing the colt had it in him all along.

Lil. E Tee (1992)

As the 1992 Run for the Roses approached, all eyes were on one Thoroughbred — Arazi. Arazi was believed to be a budding superstar, just a Derby win away from glory. The fact the Arazi’s biggest competitor, A.P. Indy, was forced to withdraw, only caused the buzz regarding Arazi to grow louder.

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Starting the race in post position 10, Lil E. Tee and jockey Pat Day weren’t expected to make much noise at Churchill Downs. The two found themselves in 10th after half a mile. Then, Arazi showcased a spectacular burst, flying past horses to move into 3rd. Lil E. Tee followed his example, shifting into 5th.

Now approaching the final stretch, the favored Arazi slowed significantly. The colt was tired, opening the door for Lil E. Tee to make a move. The horse did just that, catching the front-runner and inching ahead in the final moments to send the crowd into shock with one of the biggest upsets ever mounted at the Kentucky Derby.

Lil E. Tee pulled off a stunner, going down in history as the Thoroughbred to overtake international star Arazi.

Mine that Bird (2009)

There may be no greater story of an underdog’s rise to greatness than that of Mine that Bird. A horse that struggled to keep up with other Thoroughbreds in American races, Mine that Bird entered the Kentucky Derby 19th out of 20.

Given his placing, no one expected Mine that Bird to actually take part in the race. Days before the race, however, trainer Chip Woolley made the last-minute decision to load his 3-year-old into a trailer and make the trip from New Mexico to Kentucky.

As the horses took off, Mine that Bird was at the back of the pack, as expected. By the time the final turn approached, however, the horse managed to reach the remainder of the group. Jockey Calvin Borel and his horse stayed near to the rail, sliding past opponents and fighting to the front on the finishing stretch.

The pass was so unexpected that even the announcer, Tom Durkin, did not see the Thoroughbred pull ahead. Mine that Bird ended up taking the race by six lengths, cementing his legacy and becoming a household name.

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Giacomo (2005)

What kind of horse pulls off a Kentucky Derby victory at 50-1 odds? A gray stallion named Giacomo.

Five wide between rivals in the early stages of the race, Giacomo had his work cut out for him. Spanish Chesnut grabbed the early lead, which Closing Argument, another longshot in the field, stole midway through the race.

Remaining in 18th three quarters of a mile through the race, Giacomo began mounting his comeback. The colt moved six wide around the final turn before finding breathing room and surging ahead to the front of the pack.

Jockey Mike Smith and his horse rallied in incredible fashion, closing in and taking the lead by half a length crossing the finish line. Smith had finally claimed the Kentucky Derby crown after 12 tries, garnering immense emotion from the jockey. The victory changed the lives of Giacomo’s connections, as the team was awarded $1,639,600 for the triumph.

RELATED: Click here to watch Giacomo claim Derby victory

Rich Strike (2022)

In the days leading up to the 2022 Kentucky Derby, all seemed to be unfolding as planned. Epicenter and Zandon were the objects of attention, expected to battle for the leading position and Derby title. Though both Thoroughbreds drew unfortunate post positions, it was not insurmountable for the elite competitors.

All would change the night before Derby Day, as it was announced that Ethereal Road was officially scratched from the Run for the Roses. The next horse up to take Ethereal Road’s 20 post position was Rich Strike, who bore a record of 1-0-3 in seven lifetime starts.

RELATED: Relive Rich Strike’s unbelivable upset victory

As 147,294 gathered at Churchill Downs, none had any idea what would transpire on the infamous track. Out of the gates, Summer is Tomorrow held the early advantage, setting a Derby record for fastest quarter-mile ran (21.78 seconds).

Messier managed to catch up and take top spot at the 3/4 mile mark, only for the favored Epicenter to swiftly surpass Messier at the head of the stretch. Rich Strike, who was sitting at the back in 15th, then pulled off a miraculous comeback. The horse impressively transitioned to the rail, dodging Messier and propelling past Epicenter in the final furlong to shock America with one of the biggest upsets in Kentucky Derby history.

Rich Strike and jockey Sonny Leon were just the second duo in Derby history to claim a win from the 20th post, and the victory was the first in any form of stakes race for Leon.

How to watch the 2023 Kentucky Derby:


  • Date: Saturday, May 6
  • Time: Live coverage begins at 12 PM ET
  • Where: Churchill Downs in Louisville, Kentucky
  • TV Network: NBC
  • Streaming: Peacock, NBCSports.com, NBC Sports app

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Watch the 149th running of the Kentucky Derby on Saturday, May 6 on NBC, NBCSports.com, the NBC Sports app and Peacock from 12 p.m. to 7:30 p.m. ET.