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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

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? Rich Strike, who was a late Friday entry into the race after Ehtereal Road was scratched, won the 2022 Kentucky Derby as an 80-1 longshot.

There have been some other impressive long shots like Country House winning the 2019 Derby as a 65-1 longshot and of course Giacomo tearing up a sloppy course at Churchill Downs in 2005 to win as a 50-1 longshot.

So don’t be afraid to take a risk and put a few coins on some big odds. You might walk away with a big smile and a pocket full of cash.