Longshot Winners in the Kentucky Derby Make This Race a Great Betting Opportunity

History tells us that every so often, the Kentucky Derby will provide a shocking result. In the 137 previous runnings of the Kentucky Derby there have been a handful of huge upsets that utterly stunned the world of horse racing. Below we will take a look at some of the biggest upsets in the history of the Kentucky Derby. 5. Donerail (1913), $184.90—The son of McGee showed little in the lead-up to the Kentucky Derby while prepping in nearby Lexington, Ky., which prompted his odds to shoot up to 91-to-1. However, Donerail managed to put it all together upon his arrival at Churchill Downs. In the Derby, Donerail bided his time under restraint from jockey Roscoe Goose down the backstretch, began his move on the second turn to draw into contention and then blew past his rivals through the stretch to win going away. Donerail's managed to win only two more stakes races in his career, both of which occurred in Canada. He was retired with 10 wins from 62 starts and earnings of $15,156. 6. Mine That Bird (2009), $103.20—The son of 2004 Belmont Stakes winner Birdstone came to Kentucky via the minor racing state of New Mexico, where he was a non-threatening fourth in the Sunland Derby in his final Kentucky Derby tune-up. Sent off as the third-longest shot in the field, Mine That Bird fell way back early in the Derby, but mounted a furious rally while skimming the rail under jockey Calvin Borel to pull off the shocker. Mine That Bird would run second in the Preakness Stakes two weeks later and would never again reach the winner's circle in eight more starts. 7. Giacomo (2005), $102.60—The gray son of Holy Bull was ignored by Kentucky Derby bettors after he failed to make any sort of impact in his three prep races at Santa Anita. Giacomo's lack of early speed left him way back early in the Kentucky Derby, but that proved to be an asset as a fast early pace developed that left the front-runners out of gas in the final 400 yards. The big gray Giacomo came rumbling down the middle of the stretch and went by the field to spring the upset. Giacomo would race six more times without ever winning again. 8. Gallahadion (1940), $72.40—Owned by Ethel Mars' Milky Way Farm, Gallahadion was given no chance as bettors made the previous year's 2-year-old champion, Bimelech, the heavy 2-to-5 favorite. Gallahadion was forwardly-placed throughout the Kentucky Derby before mounting his bid along the rail in the stretch. Gallahadion managed to wear down the heavy favorite approaching the wire and had just enough left in the tank to pull the upset. Other big Kentucky Derby upsets include Charismatic's win in 1999 that paid $64.20 and Proud Clarion's win in 1967 that paid $62.20. The only other major Kentucky Derby upset of more recent vintage was Thunder Gulch's win in 1995 that paid $51.00 for every $2 bet.