Through the ages at the Kentucky Derby there have been plenty of longshots to pull upsets and reward bettors with massive payouts.

The first leg of the Triple Crown, the Kentucky Derby, has been run annually for over 140 years after all so there are bound to be several longshots to win.

Below we complied the biggest longshots to win the Run for the Roses.

MORE: 2018-19 Road to the Kentucky Derby Schedule Announced

The 8 Biggest Kentucky Derby Longshots And What They Paid

Donerail in 1913

Donerail paid $184.90 on a $2 wager to win the Kentucky Derby in 1913. To this day he is the highest-paying longshot to win the Derby at 91-1 odds.

Mine That Bird in 2009

Mine That Bird’s win arguably is more impressive than Donerail’s consider the latter was going against just seven other horses and the 2009 field had 19 head. With long odds of 50-1, Mine That Bird paid $103.20.

Giacomo in 2005

Giacomo also went off at 50-1 odds but paid a little bit less at $102.60. Still, bettors were not complaining.

Gallahadion in 1940

Gallahadion was out of Reigh Count, the mare that won the Kentucky Derby in 1928. Gallahadion, a California horse, was sent off at 36-1 odds and paid $72.40 to win.

MORE: Ranking The Best Thoroughbred Horse Racing Tracks In North America

Charismatic in 1999

Charismatic won by a neck at 31-1 odds, a value considering he was trained by the great D. Wayne Lukas. Named the 1999 Horse of the Year, Charismatic paid $64.60 for his Derby win.


Proud Clarion in 1967

Proud Clarion paid $62.20 to win at 30-1 odds and at the time had the sixth-fastest Derby time.

Exterminator in 1918

The gelding went on to win 50 of his 100 lifetime starts but his rise to fame began when he won the Derby as a 29-1 longshot to pay $61.20.

Thunder Gulch in 1995

Another great horse from D. Wayne Lukas, Thunder Gulch went on to win the Belmont Stakes as well but he wasn’t a sleeper in that race. The horse won the Derby at 25-1 and paid $51.

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