Meet the 10 biggest long shots to win the Kentucky Derby in Churchill Downs history

·4 min read

A $30,000 claimer who went from zero to hero in less than 24 hours, Rich Strike made history as the second longest shot to win the Kentucky Derby in 148 editions of the race.

As the unlikely champion gets ready for the Belmont Stakes (June 11, NBC), meet some of the other shocking upset winners from throughout the Kentucky Derby’s 148-year history.

Donerail (91-1), 1913

Over 100 years ago, an unlikely bay colt made Kentucky Derby history that would stand the test of time. Donerail was bred, owned and trained by Thomas P. Hayes, and he was ridden by Roscoe Goose, both Louisville natives.

The Kentucky Derby experience in 1913 was much different from the race of today. The purse was $6,600 (worth just under $200,000 in 2022), while the full purse of this year’s race was $3 million. There wasn’t enough space to stable Donerail at Churchill Downs, so the colt had to make an additional three-mile trek from Douglas Park before the race.

His unrivaled upset at 91-1 came with a payout of $184.90.

Donerail went on to win a handful of stakes races but broke down as a four-year-old, and his racing career never rebounded.

Rich Strike (80-1), 2022

Just one day before the 148th Kentucky Derby, Rick Dawson’s colt wasn’t even entered in the race. The Kentucky-bred grandson of Curlin was a very late addition after Ethereal Road scratched. So late, in fact, that jockey Sonny Leon had a full day of racing in Cincinnati the day before.

Rich Strike hung towards the back of the pack before turning on the rocket boosters and weaving his way to victory. His 80-1 odds made him the biggest Kentucky Derby upset in over a century and the second biggest in the history of the race.

His connections have announced that he will skip the Preakness Stakes (May 21, 4-7:30 p.m. ET, NBC) and focus on the Belmont (June 11, NBC).

Country House (65-1), 2019

The 145th Kentucky Derby was historic for several reasons. Maximum Security became the second horse in over a century of racing to be disqualified from the Derby, and Country House, who finished second but was elevated to first, cemented himself in Churchill Downs history with his win at 65-1 odds. It was the first Derby win for trainer Bill Mott and jockey Flavien Prat, and at the time, it was the second-biggest upset the Run for the Roses had ever seen.

Maximum Security comfortably cruised in front from wire to wire, but he was stripped of the win minutes after the race when racing stewards determined he had moved out of his lane and bumped his hind right leg into another horse.

The Derby was Country House’s last start, and he was retired the following February. He now stands at Darby Dan Farms in Lexington, Ky. on a $7,500 stud fee.

Mine That Bird (50-1), 2009

If you met Mine That Bird today, you’d never know the 16-year-old ranch horse made Kentucky Derby history in 2009 when he crossed the wire at Churchill Downs as a 50-1 longshot.

With jockey Calvin Borel in the irons, the Kentucky-bred descendent of Northern Dancer wasn’t just dead last for the first half of the race — he was several lengths behind the end of the pack.

In dramatic closer fashion, Borel drove Mine That Bird up the rail and pounded down the homestretch for the upset over the field of 20, which included Pioneerof the Nile, sire of Triple Crown winner American Pharoah.

Mine That Bird finished second in the Preakness, third in the Belmont and would go on to race for another season before retiring on a massive ranch in New Mexico with owner Mark Allen.

Giacomo (50-1), 2005

Jockey Mike Smith has ridden some of the most coveted horses in racing history, but it was the 50-1 longshot Giacomo that brought the now Triple Crown-winning rider his first Kentucky Derby victory.

Giacomo’s win came in dramatic fashion with the colt winning a close, three-way finish by a nose.

Two weeks later, he finished third in the Preakness and was seventh in the Belmont three weeks after that. His last win was the Grade 2 San Diego Handicap, and his final career start was back at Churchill Downs in the 2006 Breeders’ Cup Classic (G1), where he finished fourth.

The standout grey was retired to stud in Kentucky and now stands at Oakhurst Thoroughbreds in Oregon.

Watch the Preakness on Saturday, May 21 from 2 to 4 p.m. ET on CNBC and from 4 to 7:30 p.m. ET on NBC. Coverage is also available on NBCSports.com, the NBC Sports app and Peacock.

Meet the 10 biggest long shots to win the Kentucky Derby in Churchill Downs history originally appeared on NBCSports.com