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• Biggest Upsets of the Kentucky Derby
• Kentucky Derby 2020 Futures

The Kentucky Derby is a day of mint juleps, adrenaline, fascinators (fancy hats, you didn’t know?) and sometimes, huge upsets to race.

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2. The famed Kentucky Derby is set to be run on May 5, and the current Bovada Futures pool lists 33 different horses to wager on for what will be a field restricted to 20 starters. As late as February 2017, last year's Kentucky Derby winner Always Dreaming could be bet in some future.

The Kentucky Derby hasn’t been postponed since 1945, and now, 75 years later it’s taking place on September 5, 2020.

Fun Fact: The Derby was postponed because the government put a ban on horse-racing, but, Louisville citizens managed to still have a publicized race—A turtle race.

In anticipation of the big event and to remind you to not discount an underdog (or under…horse?), we take a look at 5 of the biggest upsets of the Kentucky Derby, plus, a look at Kentucky Derby Futures via Bovada ahead of the Derby.

The Biggest Upsets at the Kentucky Derby

1) Mine That Bird, 2009

No list of Kentucky Derby upsets is complete without Mine That Bird in 2009. Why? Although the gelding would never win again, Mine That Bird was essentially unknown to Derby audiences, entering the Derby at 50-1 odds and pulling off a stunning win.

Mine That Bird had trouble right out of the gate, and was even almost missed by announcer Tom Durkin since Mine That Bird was so behind the backstretch of racing horses. However, his rider, Calvin Borel who won the Derby in 2007, had a riding technique to skim the rail, which undoubtedly contributed to their win.

If you were to bet just $2 on Mine That Bird, you would’ve seen a $103.20 return, which makes Mine That Bird the third biggest upset-winner in Kentucky Derby history, along with horse Giacomo.

Finishing Distance: 6 ¾ lengths, 2 minutes & 2.66 seconds

2) Country House, 2019

Country House is probably best known for initially coming in second at the 2019 Kentucky Derby — Maximum Security is well-known for coming first and being previously undefeated, but was later disqualified due to crossing another horse at the final turn.

Country House, in addition to coming second, had some of the worst odds of the race at 65-1. In terms of payout, Country House offered a $132.40 payout.

Odds at Time of Race: 65-1

3) Donerail, 1913

Donerail raced in 1913, and managed to win when faced with terrible odds – 91-1. In 1913, Donerail offered a $184.90 payout for a $2 wager — still the biggest $2 payout of derby history.

Finishing Distance: ½ a length

Donerail, 1913 Kentucky Derby upset.

4) Gallahadion, 1940

Like others on this list, Gallahadion wasn’t favored to win with 6-1 odds. He went on to win over that year’s favorite, Bimelech, who was favored to win at 3-1. In 1940, a $2 wager on Gallahadion would earn a bettor a $72.40 payout.

Fun fact: Gallahadion’s owner was Ethel V. Mars, whose family owned the famous chocolate bar company.

A postcard from the 1953 Kentucky Derby featuring Gallahadion with one of the prizes winners receive—554 roses.

5) Native Dancer, 1953

Different from some of the other names on this list, Native Dancer was undoubtedly going to win the 1953 Derby – it went on to be the only loss in his racing career, with 21 wins out of 22 races.

Not only was Native Dancer featured on TV & known across the country, but Dancer was the favored horse to win the ’53 Derby with 3-5 odds – until an expected upset took the race.

Dark Star would go on to upset the 1953 derby, entering the race with odds at just 25-1. If you bet $2 on Dark Star in 1953, you’d receive a $51.80 payout.

Losing margin: A head

Kentucky Derby Odds: 2020 Derby Futures

Thanks to the fine folks at Bovada, we’ve got futures for the upcoming, postponed Kentucky Derby—Let’s take a look at the odds for this year’s Kentucky Derby, updated as of August 28.

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Bovada Kentucky Derby Futures Horse Racing

Who’s excited for the 2020 Kentucky Derby?!