Seven Of The Biggest Longshots To Win The Kentucky Derby

Written By Darren Cooper on May 6, 2022
Popular long shots to win the run for the roses

One of the magical things about a horse race, and the Kentucky Derby, is the beauty of picking the longshot. The horse who comes out of nowhere, the horse with the big odds, which then turns into a nice little payday after a win.

You have to be a little brave (or maybe crazy) to bet on a longshot, because they are not expected to win. But longshots do win, creating a little more magic each time.

Although sports betting in California is illegal, horse betting is legal. And if you can’t get to one of the in-person off-track-betting sites in California, you can still get in on Derby action with the TVG online platform.

Here’s a look at some of the biggest longshots to win the Kentucky Derby.

Donerail, 1913

At 91-1 odds, Donerail is the longest of shots to win the Kentucky Derby, a record that may stand forever.

Churchill Downs was undergoing construction in 1913 and Donerail was such an afterthought he was housed at stables three miles away. He had to walk three miles just to get to the race! There weren’t many cars in 1913.

The bay colt, ridden by Louisville native Roscoe Goose, started from the fifth post and rallied in the stretch to top Ten Point by a half-length. He set a new track record, covering the 1 1/4-mile distance in 2:04 4/5.

Exterminator, 1918

This is one of those ‘you don’t know what you have’ stories. Exterminator wasn’t even supposed to run in the Kentucky Derby. He was merely a training partner for Sun Briar.

Sun Briar was a star, winning five of his nine starts, but he developed ringbone before the Derby. Exterminator filled in and won on muddy track by a length at odds of 29-1.

The Derby win jumpstarted a brilliant career. Exterminator won 33 stakes races and ran until he was nine. He was eventually inducted into the National Museum of Racing and Hall of Fame.

Thunder Gulch, 1995

Thunder Gulch had won the Florida Derby and Fountain of Youth Stakes but was an afterthought in the field at 25-1.

He blew past stablemate Serena’s Song in the stretch  to win. He then ran third in the Preakness (behind fellow D. Wayne Lukas trainee Timber Country) and won the Belmont. Thunder Gulch would also win the Travers Stakes later that year.

Charismatic, 1999

This is one of the wildest rides in recent horse racing history.

Trainer D. Wayne Lukas was ready to give up on Charismatic. He entered him in a claiming race earlier in his 3-year-old season, where anyone could have purchased him for a price. However, he won the Lexington Stakes two weeks before the Derby to punch his ticket to the Run for the Roses.

Charismatic went off at 31-1, took a late lead, and held off a fast-charging Menifee to win by a neck. He then won the Preakness and had everyone dreaming of a Triple Crown (there hadn’t been one since 1978).

At the Belmont, Charismatic made the lead but yielded late and finished third. He was abruptly pulled up after the wire, and jockey Chris Antley hopped off. Antley held Charismatic’s leg in the air until help arrived.

That leg was injured, and Antley’s actions may have helped save Charismatic’s life. The horse’s story was immortalized in an ESPN 30 for 30 movie.

Mine That Bird, 2009

Legendary track announcer Tom Durkin didn’t initially see 50-1 shot Mine That Bird make his winning move up the rail.

“That is, um…Mine That Bird now coming on to take the lead,” he cried as the longshot spurted well clear of the field.

Ridden by Hall of Famer Calvin Borel, Mine That Bird was eight lengths back at the start and was the third-longest shot on the board. Horse and rider saved ground, blew past the field, and recorded the biggest margin of victory in the Kentucky Derby in more than 60 years.

Mine That Bird finished second in the Preakness and third in the Belmont. A movie, called “50-1,” was made about his story. Fittingly, Calvin Borel was played by…Calvin Borel.

Country House, 2019

Country House was 65-1 at the start of the Kentucky Derby and didn’t win, but still won. Confused?

Country House was a non-factor in the Derby prep races, finishing third in the Arkansas Derby and fourth in the Louisiana Derby. He made a late charge to finish second at Churchill Downs behind Maximum Security.

However, Maximum Security was disqualified for interference. As the second-place finisher, Country House was officially named the winner.

Mandaloun, 2021

Mandaloun was 26-1 in the 2021 Kentucky Derby. His prep races had been uneven. He won the Risen Star Stakes at Fair Grounds in New Orleans, but was seventh in the Louisiana Derby.

Mandaloun was part of a four-way stretch duel, but no horse could catch Medina Spirit, who edged Mandaloun by a half-length.

However, Medina Spirit was disqualified for an overage of betamethasone. Mandaloun was named the winner. He did not race in either the Preakness or Belmont, but has resumed his career as a four-year-old.

Photo by Patti Longmire/Associated Press
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Darren Cooper

Darren Cooper was born and raised in Southern Louisiana, just a short pirogue ride away from New Orleans. He started his journalism career at the New Orleans Times-Picayune and has been a writer and columnist in New Jersey since 1998. He's won 14 statewide press awards and earned his first Associated Press Sports Editors Top 10 award in 2022.

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