Five Biggest Long Shots to win the Kentucky Derby

Donerail (1913)

Odds: 91-1

$2 win price: $184.90

Synopsis: From an odds standpoint, this remains the biggest long shot to win the Kentucky Derby. A $15 win bet on Donerail would have netted nearly half the average annual household income in the U.S. that year.

The 1913 field consisted of only eight horses (four scratched before the race) and bettors dismissed Donerail after he failed to win any of his first three races in his 3-year-old season (he did win 4 of 18 races the previous year as a 2-year-old). Donerail rallied from behind to beat favored Ten Point by a half-length and his winning time of 2:04 4/5 was the fastest in the Derby’s 39-year history. 

Did you know?: Because of a lack of stall space at Churchill Downs in Louisville, Donerail was stabled at Douglas Park and made the nearly 3-mile walk to Churchill Downs on the morning of the race, according to several media accounts.

Giacomo (2005)

Odds: 50-1

$2 win price: $102.60

Synopsis: Giacomo was dismissed by bettors because of his 1-for-7 lifetime record, which included five consecutive losses. His most recent start was a fourth-place finish in the Santa Anita Derby. And he was up against race favorite Bellamy Road, who had recently won the Wood Memorial by more than 17 lengths.                    

A stretch-running closer with no early speed, Giacomo took advantage of a brisk early pace, which fell apart late. He was 18th after six furlongs and 11th with only a quarter mile to run. Stuck behind a wall of horses, jockey Mike Smith rallied the gray colt eight-wide down the stretch to pass an even bigger long shot, Closing Argument, and win by a half-length.

Did you know?: The Giacomo-Closing Argument (71-1) $2 exacta returned $9,814.80, the highest in Derby history. The payoffs for the trifecta ($133,140.80) and superfecta ($864,253.50) also remain Derby records.

Check out the Gambling.com Horse Racing Picks Page to keep up with long shots for this year's Kentucky Derby

Mine That Bird (2009)

Odds: 50-1

$2 win price: $103.20

Synopsis: The 19th of 20 horses to qualify for the 2009 field, Mine That Bird, a $9,500 purchase, was coming off a fourth-place in the Sunland Derby in New Mexico, a lackluster finish in a low-level prep race.  

He had three things going for him on that first Saturday in May: an affinity for a sloppy track, the collapse of a fast early pace and a ground-saving, rail-skimming ride by Calvin Borel. Mine That Bird trailed by more than 20 lengths at one point, then rallied inside to blow past the entire field and win by 6 3/4 lengths, the largest margin of Derby victory since Assault (eight lengths) in 1946. He would go on to finish second in the Preakness and third in the Belmont Stakes — both at significantly lower odds.

Did you know?: Mine That Bird’s stunning victory in the 2009 Run for the Roses inspired the film ’50-1,’ released in 2014. Jockey Borel played himself. 

Country House (2019)

Odds: 65-1

$2 win price: $132.40

Synopsis: Country House was the second horse to cross the finish line in the 2019 Derby, yet found himself in the winner’s circle after the Churchill Downs stewards disqualified first-place finisher Maximum Security for interference with another horse down the stretch. The stewards took 22 minutes to decide the outcome. It was the first time in Derby history that a winner was taken down (and subsequently placed 17th) for a foul during the race.

Country House was the second-largest price in the 19-horse field because he was 1-for-6 lifetime and finished a non-threatening third and fourth in his two most recent preps. Starting from the No. 18 post, he raced mid-pack most of the way, was largely unaffected by the interference incident and rallied for second, nearly two lengths behind Maximum Security.

After the race, the two sides had very different views of the controversial disqualification. Country House trainer Bill Mott said: “I knew the stewards had a very, very difficult decision. I’m damn glad they put our number up.’’ Maximum Security owner Gary West called the stewards’ decision “the most egregious disqualification in the history of horse racing.’’ 

Did you know?: Country House did not run in the Preakness and would never race again because of a series of injuries. A lawsuit filed by the owners of Maximum Security was unsuccessful in district court and the U.S. Court of Appeals rejected an appeal.

Rich Strike (2022)

Odds: 80-1

$2 win price: $163.60

Synopsis: Rich Strike wasn’t even a part of the 2022 Derby field until Ethereal Road scratched the morning before the race, allowing him to draw in from the also-eligible list. Rich Strike’s resume was modest at best: a third-place finish in the Jeff Ruby Steaks at Turfway Park accounted for nearly all of his Derby points.

Starting from the outermost post 20 as the longest shot in the field, Rich Strike took advantage of the same type of early pace meltdown that would benefit Giacomo and Mine That Bird. With a quarter mile to the finish, he was 15th, nearly eight lengths back. As the leaders faltered, jockey Sonny Leon deftly maneuvered Rich Strike between and then inside horses to get up by three-quarters of a length. It was the first Derby appearance for both Leon and trainer Eric Reed, who fell to the ground after Rich Strike crossed the wire first.

Did you know?: Rich Strike made the Derby field as the 21st qualifier with only 21 points. This year, that point total would have ranked 35th on the leaderboard, meaning Rich Strike would have no chance to make the 2023 Derby field.