Who Are The 5 Biggest Kentucky Derby Longshot Winners of All-Time?

Biggest Kentucky Derby Long Shots

Getty Jockey Calvin Borel wearing black and silver rides on Mine That Bird.

After heavy favorite Omaha Beach dropped out of the running, the Kentucky Derby field is wide open for some of the longshots to make a play. With a number of talented horses who don’t stand out tremendously from the pack, just about any horse in the running could have an actual chance at winning.

While Bob Baffert’s trio of favorites are still standing, even oddsmakers are skeptical. Oddsmakers only are giving the favorite to win the race, Game Winner, a 5-1 chance. With almost every horse having an opportunity to win and offering a great payout, the 2019 Kentucky Derby should be one of the most closely contested races in years.

So just who are the biggest Kentucky Derby longshots of all-time?


1. Donerail – 91/1


The Longest Odds: Jockey "The Golden Goose" | Kentucky Life | KETRoscoe Goose lived the dream of every Kentucky-born jockey—and he did it riding the most unlikely of horses. With odds of 91 to 1, Goose rode Donerail to victory in the 1913 Kentucky Derby. Donerail remains the longest shot ever to win the Derby—a $2 bet on him returned $184.90. Roscoe was the Golden Goose.…2014-05-05T18:22:53.000Z

Clocking in at by far the heaviest odds ever for a longshot, Donerail won the 1913 Kentucky Derby at an astounding 91-1 odds. For reference, no horse this year even clocks in remotely close as the heaviest of odds go to Gray Magician and Master Fencer, both of which sit at 50-1. Donerail wouldn’t lead at any point of the race, instead, turning on the burners to close out down the final stretch a JUST eke out the biggest Derby upset in history.


2. Mine That Bird – 50/1


2009 Kentucky Derby "Mine That Bird" in HD w/perfect sound.The 135th running of the Kentucky Derby. Mine That Bird Amazing Finish, dead last to first.2009-05-03T01:52:55.000Z

A bit more recent compared to Donerail’s 1913 exploits, Mine That Bird was a 50-1 underdog in the 2009 race yet won by a shockingly large margin. Despite trailing most of the race, Mine That Bird dusted the competition down the stretch and finished first by 6 3/4 lengths.


3. Giacomo – 50/1


2005 Kentucky Derby (+Post-Race Results)TopThoroughbred’s #FlashFromThePast: 2005 Kentucky Derby Here’s an article about the race written by USATODAY: -Spoiler Alert- Giacamo shocks derby field winning at 50-1 "LOUISVILLE — Giacomo, a 50-1 long shot, came down the center of the race track and broke away from the pack in the stretch to win Saturday's 131st Kentucky Derby, resulting in…2016-09-06T07:37:51.000Z

Giacomo had his turn at the upset in 2005. One of the most memorable Kentucky Derby upsets in history, Giacomo was nowhere near the front of the pack before making his historic charge to the finish. Also listed at 50-1 but paying out a fraction less than Mine That Bird, Giacomo’s incredible ride grants him the third biggest upset in Kentucky Derby History.


4. Gallahadion – 36/1


Gallahadion wins 1940 Kentucky Derby!Gallahadion wins 1940 Kentucky Derby with jockey Carroll Bierman.2016-04-05T21:23:19.000Z

Gallahadion won the Kentucky Derby in 1940 with 36-1 odds. Gallahadion had run terribly in his two races leading up to the Kentucky Derby and despite having looked the part of a Derby contender at times, was mostly overlooked due to his recent form. Rather than folding under pressure again, Gallahadion put his talent on full display and dusted his competition in the Derby.


5. Charismatic – 31/1


Kentucky Derby [1999] Charismatic2010-05-02T01:55:34.000Z

One of the best feel-good stories in Kentucky Derby history, Charismatic was running in claiming races not long before making a historic Derby run. Charismatic would not only win the Derby at 31-1 odds but would go on to win the Preakness shortly after. Unfortunately, Charismatic’s career would come to an abrupt end while leading the Belmont before suffering a leg fracture.


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