Longest Shots to Win Kentucky Derby

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Saturday’s Kentucky Derby was among the most controversial of the 145 all-time races at Churchill Downs. Maximum Security won the event, entering as the second-highest favorite at 9-2 odds. An inquiry, however, turned the most exciting two minutes in sports into a nearly 10-minute wait. A long review ultimately ruled that the horse had committed interference, straying too wide and bumping into another horse. The disqualification was the second ever in the race’s history, and the first because of such an inquiry.

That means that Country House is the winner, and it’s a stunning one. A 65-1 longshot going in, he becomes one of the unlikeliest victors ever at the Kentucky Derby. Here’s are the betting line underdogs who won, and here’s how they fared in the other Triple Crown races:

Donerail (1913):

The only other horse with longer odds than Country Horse was Donerail over 100 years ago. A 91-1 longshot, such odds rarely exist in today’s races. Alas from the fifth position he wound up winning by a half-length over Ten Point, setting the track record with a time of just under 2:05. By all accounts the horse did not run in the final two legs of the Triple Crown – or at the very least, he did not place or show.

Country House (2019):

There’s always going to be the asterisk involved, but history will show that Country House is the second-largest underdog to take the Kentucky Derby crown. A 65-1 longshot, the victory runs his career record to 2-2-1 heading into the Preakness. Surely his odds at Pimlico will be slightly better than 65-1.

Giacomo (2005):

The gray stallion came in at 50-1 odds, but led by Mike E. Smith held off the favorite Afleet Alex to win the 2005 Derby. In the process the horse may have denied history, too, as Afleet Alex went on to win the final two legs of the Triple Crown (remember, at this time there hadn’t been a Triple Crown winner in nearly 30 years). Giacomo, meanwhile, settled for third at Pimlico and seventh at Belmont.

Mine That Bird (2009):

A decade ago Mine That Bird went on a final stretch that lives on. Sitting in last place and coming in at 50-1, there was little reason to believe the horse would not only win the race, but do it convincingly. At the top of the stretch, though, jockey Calvin Borel took Mine That Bird from last to first, winning by seven lengths, the largest margin of victory in six decades. He’s one of only two geldings to win the race in the last 90 years, but the luck ran out. He finished second at the Preakness, third at Belmont and retired from racing the following year.

Gallahadion (1940):

Bimelech was such an odds-on favorite that his betting line was 2-to-5 – in other words, place a five dollar bet to win two dollars. Alas, the 36-1 Gallahadion went stride-for-stride with the favorite the whole way, until finally passing and holding on over the final quarter mile. Gallahadion would finish third in the Preakness, but was unable to finish the lengthy Belmont Stakes and did not place, while Bimelech won each of the final two legs.