Biggest Long Shot Winners In Kentucky Derby History

NEW YORK (CBSNewYork) — Saturday will mark the 143rd running of the Kentucky Derby. Here are the five biggest underdogs to ever win the race.

1999: CHARISMATIC (31.3-to-1)

Charismatic / 1999 Kentucky Derby

Jockey Chris Antley celebrates after riding Charismatic to victory in the 1999 Kentucky Derby. (Photo by Robert Sullivan/Getty Images)

A descendant of Secretariat, Charismatic finished a head in front of Menifee. Charismatic went on to win the Preakness and was leading into the final furlong of the Belmont Stakes before fading.

1940: GALLAHADION (35.2-to-1)
Gallahadion was the son of 1928 Kentucky Derby champ Reigh Count, but was considered a real long shot in the race. He defeated the overwhelming favorite, Bimelech, who had 2-to-5 odds at Churchill Downs.

2009: MINE THAT BIRD (50-to-1)

Mine That Bird / 2009 Kentucky Derby

Jockey Calvin Borel, atop Mine That Bird, crosses the finish line to win the 135th running of the Kentucky Derby on May 2, 2009. (Photo by Jamie Squire/Getty Images)

After falling far behind at the start on a muddy track, jockey Calvin Borel and Mine That Bird stuck to the rail en route to winning by 6 3/4 lengths. Mine That Bird finished second in the Preakness (with Borel aboard winner Rachel Alexandra) and third at the Belmont.

2005: GIACOMO (50.3-to-1)
What was more surprising than Giacomo overcoming long odds to win the Derby was that the second-place finisher, Closing Argument, was also a 50-to-1 long shot. Giacomo finished third at the Preakness, but just seventh at the Belmont.

1913: DONERAIL (91.45-to-1)

1913 Kentucky Derby champion Donerail

1913 Kentucky Derby champion Donerail

The lead at the Derby in 1913 changed hands — or should we say hooves? — several times. But Donerail eventually slipped past Ten Point down the stretch to win by half a length.

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