The Kentucky Derby is always a thrilling and captivating event. However, when there's an underdog leading the pack or attempting to pull off an upset, no one can deny it gets even more interesting.
America has always been obsessed and intrinsically connected to underdogs. Maybe it's because the nation was born from a ragtag group defeating the most complex and sophisticated army in the world.
Or maybe it's the gambling.
But whatever the reason may be, everyone agrees that a great underdog story is about as good as it gets. So with the 2025 Kentucky Derby just a few days away, let's reflect on some of the biggest underdog winners in the race's history.
What Defines a Longshot in Horse Racing?
A longshot is a horse that is not expected to be successful and therefore has high odds. The higher the odds, the lower the perceived chance of said horse winning.
There are a number of reasons a horse can become a longshot in the Kentucky Derby. It might have to do with weather, with its position at the starting gate or with recent history.
For example, if a particular horse doesn't run well in the mud, but it was supposed to rain on the morning of the Kentucky Derby, the odds would likely reflect that.
Or if a horse had performed poorly in its last few races, the odds will likely reflect that, too.
The Biggest Longshot to Ever Win the Kentucky Derby
In 1913, Donerail's odds to win the Kentucky Derby were 91-1. Bred, owned and trained by Thomas P. Haynes, Donerail started the race in a fairly unassuming way. He didn't bolt to the front of the pack, but rather settled in the middle of it.
Going into the final stretch, jockey Roscoe Goose pushed Donerail from fifth place to a victory in the Run for the Roses. He ran a then-record 2:04.80.
Donerail, despite winning the most famous horse race in the world, struggled to ever capture that form again. In 62 career races, the horse won just 10 of them. Still, Donerail became somewhat of an American hero in the early 1910s.
Other Notable Derby Longshots Who Shocked the Field
Rich Strike (2022): Rich Strike is the second-biggest underdog winner in Kentucky Derby history, coming in with 80-1 odds. The horse wasn't even supposed to be in the race. An injury the day prior to the Derby put Rich Strike into the field.
Not to mention the fact that Rich Strike had won only one race in his career, and the Kentucky Derby was his eighth start. His jockey, Sunny Leon, had never rode in the in Kentucky Derby before.
During the actual race, Rich Strike was hovering around 10th place going into the final half-lap. He surged seemingly out of nowhere, maneuvering through the rest of the field to win by nearly a length.
Country House (2019): Country House's odds were 65-1 and the horse didn't actually cross the finish line first at the 2019 Kentucky Derby. Maximum Security was originally thought to have won the race by about two lengths.
But, Country House's jockey, Flavien Prat, filed an official objection at the conclusion of the race. He claimed that Maximum Security had veered out of its lane and contacted another horse, War of Will. War of Will then contacted Country House.
The result was that Maximum Security was disqualified. It was the first time in Kentucky Derby history that a horse was disqualified.
Mine That Bird (2009): Mine That Bird entered the 2009 Kentucky Derby with 50-1 odds and for most of the race, it made plenty of sense. After running 3/4 of a mile, Mine That Bird was in last place.
And then everything changed.
Running alongside the rail, Mine That Bird began to sprint by the field, maneuvering slightly to the outside, just to work its way back to the rail and complete its surge. It was so improbable that it sounded like the announcers weren't even sure at first which horse had managed to complete the comeback.
In the end, Mine That Bird won by 6 3/4 lengths.
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This article was originally published on www.si.com as Biggest Longshots to Ever Win the Kentucky Derby.