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Which horse was the biggest long shot to win the Kentucky Derby?

One horse rises above them all in being unexpected to win at Churchill Downs. Here’s the biggest upset in the history of the Run for the Roses.

Horses head down the stretch in front of the twin spires in the second race before the 146th Kentucky Derby at Churchill Downs. Jamie Rhodes-USA TODAY Sports

UPDATE: Rich Strike won Saturday’s Kentucky Derby as an 80-1 longshot. This is the second biggest upset in Kentucky Derby history.

With 20 mounts now allowed in the field annually, it’s rarely a total surprise to a see an unexpected horse break through to win in the Kentucky Derby. The nature of the sport and the chaos of the mass start allows for certain jockeys and horses to often break through for whatever reason.

But when it comes to the betting money being wrong, one Derby winner stands above the rest. And the biggest upset in the history of the Kentucky Derby was in just an eight-horse field.

In 1913 Donerail started on the rail, as the No. 1 horse closed as a 91/1 shot at the window. The favorite was Ten Point in the No. 2 position, who closed at 11/5 and ended up paying only 3.50 to place despite leading at the final turn. The Thomas P. Hayes-owned Donerail won by a half-length, and etched his name in history.

In 62 career starts, Donerail won 10 ten times, placed 11, and showed 10 more. He finished with lifetime earnings of $15,156, including $5,475 paid on May 10th, 1913 at Churchill Downs.

The second biggest upset by the numbers? It was just three years ago when Country Home took home the trophy at a whopping 65-1 price in 2019. It took the disqualification of the favorite in Maximum Security, but those with tickets for Country Home certainly weren’t complaining.