Greatest Kentucky Derby Upsets

Mine That Bird's stunning Kentucky Derby win at odds of 50-1 provided the second highest payoff in the history of the race, but where does it rank in terms of great horses that lost the Derby to "lesser" opponents.  We've put together a list of some of the upset Derby winners, with a brief explanation of each race below the poll, to help you rank the horses.

For a more detailed look at some of the greatest upsets, we suggest reading the best-selling book, Greatest Kentucky Derby Upsets.

Donerail - largest $2 payoff in Derby history: $184.90

Paul Jones - beat the infamous Upset, the only horse to defeat Man o' War

Bold Venture - a 20-1 shocker by a head over 4-5 favorite Brevity

Gallahadion - paid a whopping $72.40 to win, at the time the second biggest payoff in Derby history, defeated 2-5 favorite Bimelech

Dark Star - handed Native Dancer his only career defeat

Iron Liege - beat a stellar field that included Gallant Man, Bold Ruler, Round Table and Federal Hill

Decidedly - pulled the upset over Ridan

Proud Clarion - $62.20 winner defeated the great Damascus

Charismatic - went off at 31-1; gave trainer Wayne Lukas his fourth Derby victory

Giacomo - rewarded his backers with a $100 mutuel at the expense of Afleet Alex, who would go on to win the Preakness and Belmont

Mine That Bird - another improbable winner at 50-1, came from last place under Calvin Borel 

To participate, use your cursor to drag the selections on the left (currently arranged chronologically) to the blank placeholders on the right. Once you have completed ranking all of the horses, submit your entries and compare your results to the rest of the community. A first place ranking will earn 10 points, second place receives 9 points, and so on.  

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