The Kentucky Derby keeps proving one thing: Don’t trust the favorite

From Donerail’s 91-1 miracle in 1913 to Rich Strike shocking the world in 2022, the Kentucky Derby has a long history of making believers out of longshot backers. Saturday could be next.

The Kentucky Derby favorite hasn’t won since Justify in 2018. Last year, Sovereignty was at 7-1 odds and rallied from the back of the pack on a sloppy track to run down favorite Journalism. That wasn’t even close to the biggest longshot to win this race.  

With Great White going off at 50-1 on Saturday, history’s money is on the longshots. Here is a look at the five biggest upsets the Run for the Roses has ever produced.  

Donerail, 1913  

ODDS: 91-1 

The record has stood for 113 years and might never fall. Donerail walked about three miles on dirt and cobblestone to reach the track that morning. He was stabled at a separate facility that day because Churchill Downs was overcrowded. Owner Thomas P. Hayes was just looking for a piece of the purse, hoping to finish in the top five. Instead, jockey Roscoe Goose kept Donerail off the pace letting the favorites Ten Point and Foundation race out front. In the final stretch, Goose let Donerail loose and he flew past the favorites to win by half a length.  

The $2 win ticket paid $184.90. It is still the largest payout in Derby history.  

Rich Strike, 2022 

ODDS: 80-1 

Added to the field as an alternate the day before the race when Ethereal Road was scratched, Rich Strike came in at 80-1 odds. He started outside, post 20, as jockey Sonny Leon moved him into 15th within the first mile. Rich Strike and Leon threaded through traffic to move to the inside rail. From there, they ran down the 4-1 favorite Epicenter to get Rich Strike’s first ever graded-stakes win.  

The $2 ticket paid off $132.40.  

Country House, 2019 

ODDS: 65-1 

This might be the most unlikely Derby history in modern history, because he didn’t cross the finish line first. Maximum Security did and then was disqualified. After a 22-minute conference at the end of the race, Maximum Security was stripped of the win when the race’s stewards determined that he had caused a chain-reaction of interference in the stretch. Country House had won just one race in six career starts before claiming the Derby roses.  

A $2 ticket on him to win paid out $132.40 

Giacomo, 2005 

ODDS: 50-1 

Owned by music executive Jerry Moss, Giacomo had one career win to his name entering the Derby. He came out slow, sitting near the back of the pack through most of the race and then made a spectacular charge through heavy traffic to win in a three-horse photo finish by half a length. He joined his grandfather, the Hall of Famer Seattle Slew, as a Kentucky Derby winner. The favorite, Bellamy Road finished seventh.  

The payout for a $2 win ticket was $102.60.  

Mine That Bird, 2009 

ODDS: 50-1 

While the Derby contender arrived in Louisville by private jets and luxury vans, Mine That Bird traveled more than 1,200 miles in a regular horse trailer hitched to the back of trainer Chip Woolley’s truck. Jockey Calvin Borel, who had won the 2007 Derby on Street Sense, guided Mine That Bird from eight lengths behind at the first turn to the rail. They started picking off horses one by one and by the time NBC announcer Tom Durkin spotted them, Mine That Bird was already three lengths ahead. He went on to win by 6 ¾ lengths, the largest margin of victory in 60 years.  

The $2 ticket paid $103.20.