All-Time Biggest Upsets and Longshots to Win the Kentucky Derby

At Churchill Downs, it only takes two minutes to achieve immortality. As the first leg of the Triple Crown, legendary steeds – Secretariat, Man O’ War, Seabuiscit – started their historic journey to greatness at the Kentucky Derby. But equally as memorable are the unheralded horses who exceeded all expectations to receive the blanket of roses. Let’s take a look at the five horses throughout history that overcame the greatest odds to claim the Kentucky Derby.

This year’s edition is just around the corner. Find out all you need to know about the big race with our complete Kentucky Derby preview, as well as the Kentucky Derby experts’ picks.
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Top 5 Biggest Long Shots Kentucky Derby Winners

5. Charismatic (1999)

Odds: +3,100
Payout for a $2 bet: $62.00

[sc:horses240banner ]Charismatic was just about the least appealing starter heading into the 1999 Kentucky Derby. He was only months removed from taking part in a claiming race could have been had for a mere $62,500. His jockey was the embattled Chris Antley, who had seriously considered retirement after battling weight issues and substance abuse. Obviously, no one gave the horse a shot.

But against the odds, Charismatic went into Churchill Downs and charged his way to one of the unlikeliest Derby wins ever.

4. Gallahadion (1940)

Odds: +3,600
Payout for a $2 bet: $72.00

Despite his championship pedigree – he was the son of Champion sire Sir Gallahad III – Gallahadion was quite inconsistent in the buildup to the 1940 Derby. He lost badly in his first two races, but went on to win his last two starts. However, that wasn’t enough to sway the oddsmakers, who priced him at 36-1 to win. Bimelech was the heavy favorite that year at 2-5.

Gallahadion scoffed at those odds right out of the gate. He was an early front-runner, and remained in the mix before making a final push down the wire. He eventually outlasted the favorite en route to the major upset.

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3. Giacomo (2005)

Odds: +5,000
Payout for a $2 bet: $100.00

Giacomo had a reputation for being a slow starter, but a strong finisher. Unfortunately, the former didn’t exactly endear him with the oddsmakers. He didn’t do anything to change their minds in his three pre-Derby races at Santa Anita, and was eventually made a huge 50-1 longshot heading into the Derby.

Those odds looked to have been spot on, as he fell behind early in the race. But as the front-runners faded over the stretch, Giacomo sprang into action. He charged down the middle of the pack on his way to the massive upset.

2. Mine That Bird (2009)

Odds: +5,000
Payout for a $2 bet: $100.00

Four years later, Mine That Bird – a similar 50-1 longshot as Giacomo – called Giacomo’s feat and raised the difficulty. Mine That Bird also needed to do things the hard way, as he fell behind early in the 2009 Derby. But jockey Calvin Borel wasn’t to be denied.

Borel made a ballsy move on the inside, coming perilously close to the rail, which paid off handsomely – for him and anyone who bet on Bird. He grabbed the lead, and proceeded to break away from the pack with a tremendous final surge.

1. Donerail (1913)

Odds: +9,100
Payout for a $2 bet: $182.00

It’s been more than a century, but no one has come close to dethroning Donerail as the ultimate Kentucky Derby longshot. A complete afterthought at 91-1 back in 1913, Donerail probably shouldn’t have bothered galloping into Churchill Downs with such astronomically high odds.

But there he was, and he defied those odds. He was held back on the backstretch by jockey Roscoe Goose, but he made his move down the homestretch to comfortably win by two lengths. He remains – and likely will remain – the highest paying winner in the race’s illustrious history.

Looking for this year’s super long shot? Don’t miss our look at the experts’ sleeper picks for the 2015 Kentucky Derby.
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