Biggest longshots to beat the odds and win the Kentucky Derby

  • Biggest longshots to beat the odds and win the Kentucky Derby

    There hasn't been a Leicester City to win the Kentucky Derby — a 5000-to-1 longshot — but the Run for the Roses isn't always won by the favorites.

    In the more than 140 years the Kentucky Derby has been run, a few bettors have scored a handful of big paydays by backing the most unlikely of underdogs.

    MORE: All-time Derby winners | 2016 photos

    For reference, here are the odds to win the 2017 Kentucky Derby in a relatively close field with no clear-cut favorite. 

    2017 Kentucky Derby odds 

    Classic Empire 4/1
    Always Dreaming 5/1
    McCraken 5/1
    Irish War Cry 6/1
    Girvin 15/1
    Hence 15/1
    Gunnevera 15/1
    Gormley 15/1
    Lookin At Lee 20/1
    Thunder Snow (IRE) 20/1
    Irap 20/1
    J Boys Echo 20/1
    Tapwrit 20/1
    Practical Joke 20/1
    Untrapped 30/1
    State of Honor 30/1
    Battle of Midway 30/1
    Patch 30/1
    Fast and Accurate 50/1
    Sonneteer 50/1

    Now, here are eight of the biggest longshots to win the Kentucky Derby.

  • 1 Donerail, 1913

    Field size: 8

    Time: 2:04.80

    Length victory: 1/2

    Odds: 91-1

    Donerail, from the fifth post, won driving and passed the field in the final sixteenth of a mile. He bested Ten Point by half a length. 

    He is still the longest shot to ever win the Kentucky Derby, and that's a mark that should stand — few horses are listed that high in today's racing world.

    MORE: 2016 Kentucky Derby odds

  • 2 Mine That Bird, 2009

    Field size: 19

    Time: 2:02.66

    Length victory: 6 3/4

    Odds: 50-1

    Mine That Bird, along was five other horses, was the longest shot in this field at 50-to-1. And he certainly looked the part through much of the race. But Calvin Borel asked Mine That Bird to go at the top of the stretch, taking him from last to first to win by nearly seven lengths. It was the biggest victory in the Derby in more than 60 years.

    This had the potential for an epic call, but announcer Larry Durkin was so confused by Mine That Bird's surge that it took him a second to even identify the horse, then stumbled on his words as the Canadian colt blew by the field.

    MORE: List of Kentucky Derby winners

  • 3 Giacomo, 2005

    Field size: 20

    Time: 2:02.75

    Length victory: 1/2

    Odds: 50-1

    Giacomo actually denied a Triple Crown bid with his late charge in the 2005 Kentucky Derby. Afleet Alex won the Preakness and Belmont after finishing third in this race.

    MORE: Kentucky Derby records, all-time leaders

  • 4 Gallahadion, 1940

    Field size: 8

    Time: 2:05

    Length victory: 1 1/2

    Odds: 35-1

    Gallahadion wasn't just a long shot — no other horse was really given a chance to knock off Bimelech, who was a 2-to-5 favorite. Bimelech went on to win the Preakness and Belmont; Gallahadion finished third at Pimlico but the extra distance proved too much and he went unfinished in the Belmont.

    In the Derby, Gallahadion started from the post and stuck with the speedy Bimelech early, then passed him in the final quarter mile. He had little left in the tank as he crossed the finish line.

    MORE: When is the 2016 Kentucky Derby?

  • 5 Charismatic, 1999

    Field size: 19

    Time: 2:03.29

    Length victory: Neck

    Odds: 31-1

    Trained by the legendary D. Wayne Lukas, Charismatic got off to an early lead in the 1999 Kentucky Derby, dropped back, then drove down the stretch to hold off the even harder-charging Menifee by a neck. Had the race been even a few feet longer, he would have lost.

    Charismatic won the Preakness and led the Belmont Stakes in the final furlong, but got passed by Lemon Drop Kid and eventually finished third. He suffered a broken front left leg in that race, and jockey Chris Antley alertly jumped off the horse to hold it up, which saved his life. Antley later said he sensed the injury and eased up Charismatic in that last furlong to avoid further injury.

    MORE: Relive American Pharoah's epic Derby win

  • 6 Proud Clarion, 1967

    Field size: 14

    Time: 2:00.60

    Length victory: 1

    Odds: 30-1

    Proud Clarion had never won a stakes race when he went off in the 1967 Derby at 30-to-1. He only won two more races in the rest of his 3-year-old season.

    MORE: Best Kentucky Derby hats

  • 7 Exterminator, 1918

    Field size: 8

    Time: 2:10.89

    Length victory: 1

    Odds: 29-1

    Exterminator wasn't even supposed to be in the Derby, but replaced training partner Sun Briar a few days before the 44th Run for the Roses. He drove late through the mud to pick up a win by a length.

    Exterminator ran 99 races in his storied career, and was twice voted Horse of the Year. He won 50 of those races and earned, in today's dollars, a little over $3 million.

  • 8 Thunder Gulch, 1995

    Field size: 19

    Time: 2:01.27

    Length victory: 2 1/2

    Odds: 25-1

    Thunder Gulch wound up winning the Kentucky Derby and Belmont Stakes, but fell in the Preakness to miss a Triple Crown. At Churchill Downs, he remained within striking distance at the top of the stretch before easily putting the field away by 2 1/2 lengths. He was retired at the end of that season and is still living at Coolmore Stud in Versailles, Ky.

By using Yahoo you agree that Yahoo and partners may use Cookies for personalisation and other purposes