The Biggest Longshot Upsets In Kentucky Derby History

It is Kentucky Derby time in the Bluegrass!

Right now, over at Churchill Downs in Louisville, the races before the races are underway at Oaks Day, the second-highest attended race day in the United States. Tomorrow, 150,000-plus spectators will attend The Most Exciting Two Minutes In Sports and all of the races leading up to it, when at 6:57 p.m. and not a minute sooner, a shortened, nineteen-horse field will Run For The Roses.

Currently, Forte is the betting favorite at 9-2 odds to win, ahead of Tapit Trice and Angel of Empire, each at 6-1. For our longshot gamblers and shot-shooters, plenty of Hail Marys are on the board, like King Russell, the new entry, with the longest odds at 50-1.

To give King Russell and his fellow dreamers some confidence heading into tomorrow, let’s remember some past Derby winners that entered the race in a similar spot, only to outpace the favorites to the finish line.

Here are some of the biggest upsets in Kentucky Derby history, along with the champ’s odds before they shocked the world on the first Sunday in May. We won’t have to go back very far in the history books to find one.

Rich Strike, 2022 (80-1)

King Russell can look to last year for an upset winner at the Kentucky Derby. Last May, Rich Strike won the Derby with the second-longest odds in the 148-year history of the race at 80-1. The come-from-behind charge began from the eighteenth place after the first half-mile, a full seventeen lengths behind the leaders. Rich Strike completely the improbable comeback when he passed Epicenter down the stretch to win by three-quarters of a length.

Mine That Bird, 2009 (50-1)

Mine That Bird was a 50-1 longshot in the 2009 Kentucky Derby, but he shocked the world with a stunning come-from-behind victory. Jockey Calvin Borel guided Mine That Bird along the rail, passing eighteen horses to win by nearly seven lengths.

Giacomo, 2005 (50-1)

Like Mine That Bird in 2009, Giacomo was a 50-1 longshot winner four years earlier in the 2005 Kentucky Derby. Giacomo managed to outrun nineteen other horses to win by half a length. Mike Smith rode Giacomo to Smith’s only Derby win in his Hall of Fame career.

Thunder Gulch, 1995 (25-1)

D. Wayne Lukas’s Thunder Gulch was a 25-1 longshot in the 1995 Kentucky Derby, but he managed to pull off a come-from-behind victory to win by a length and a quarter. Soon after, he won the Belmont Stakes as the betting favorite in New York.

Charismatic, 1999 (31-1)

Another D. Wayne Lukas winner, Charismatic was a 31-to-1 longshot in the 1999 Kentucky Derby. Jockey Chris Antley guided Charismatic to the win, making him one of the biggest underdogs to ever win the Derby.

Donerail, 1913 (91-1)

Donerail was a 91-to-1 longshot in the 1913 Kentucky Derby, making him the most significant upset winner in history. Despite the long odds, Donerail pulled off the victory, winning by half a length and paying $184.90 on a two dollar bet.

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Will we add one more to this list tomorrow?