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The 5 biggest long-shot winners in Kentucky Derby history

The biggest long-shot winner in the Kentucky Derby’s 149-year history was Donerail, who won “The Run for the Roses” in 1913 at 91-1 odds.

A $2 win bet paid $184.90 on the horse after its half-length win at Churchill Downs over front-running favorite Ten Point.

The next four horses with the longest odds ever to win the Derby have cashed tickets for bettors in the 21st century.

Rich Strike (2022): 80-1

The second-biggest long shot to win the Derby was not in the field until Ethereal Road was scratched the day before, with Rich Strike being added from the also-eligible list. Kentucky Derby favorite Epicenter was leading and dueling down the stretch with Zandon when Rich Strike — the longest shot in the 20-horse field — came charging up the rail for a stunning upset by three-quarters of a length.

Houston furniture store owner Jim “Mattress Mack” McIngvale lost $2.6 million in wagers on the race, including $1.5 million on Epicenter to win, that would’ve paid an estimated $12 million had the favorite prevailed.

Country House (2019): 65-1

Maximum Security crossed the finish line first at Churchill Downs in 2019, but was disqualified for interference 22 minutes after the race. Country House, a 65-1 long shot who crossed the finish line second, was then declared the winner.

A horse player at The Mirage racebook turned $8 into $78,000 when Country House was declared the winner. He hit matching $4 superfectas that paid $51,400 each ($39,000 after taxes).

Mine That Bird (2009): 50-1

The son of 2004 Belmont Stakes winner Birdstone had the third-longest odds in the 19-horse field. He had trouble out of the starting gate on a sloppy track and was eight lengths behind the rest of the pack before pulling away to win by 6¾ lengths for the longest margin of victory in more than 60 years. A $2 win bet paid $103.20.

Giacomo (2005): 50-1

The big, gray colt won the 2005 Kentucky Derby by a half-length over Closing Argument, a 70-1 long shot. A $2 win bet paid $102.60.

Contact reporter Todd Dewey at tdewey@reviewjournal.com. Follow @tdewey33 on X.

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