The Kentucky Derby is famous for crowning champions, but it is also famous for crushing the dreams of bettors who load up on the favorites. Every now and then, a horse with no business being in the winner’s circle finds a way to get there. When that happens, the payouts become legendary, and so does the horse.
So who holds the title of biggest longshot to ever win the Run for the Roses? That honor belongs to Donerail, who shocked Churchill Downs in 1913 with 91-1 odds. More than a century has passed, and no winner has come close to topping that mark.
Donerail and the 1913 Upset
Donerail entered the 1913 Kentucky Derby as a complete afterthought. The colt was bred, owned, and trained by Thomas P. Hayes of Lexington, Kentucky. His jockey, Roscoe Goose, was a Louisville native who would later be inducted into the inaugural class of the Kentucky Athletic Hall of Fame.
The conditions of the race were rough by modern standards. Churchill Downs was so crowded that Donerail had to be stabled at Douglas Park, which meant a three-mile walk on dirt and cobblestone before the race even began. The purse for the 39th running of the Derby was just $6,600, a fraction of what today’s winners take home.
Despite all of that, Donerail rallied from the fifth position at the top of the stretch and ran down the favored Ten Point to win by half a length. A two-dollar win ticket paid back $184.90. That payout still stands as one of the most remarkable cashes in American horse racing history.
Why Donerail’s Record Has Stood for So Long
Modern horse racing has produced plenty of upsets, but the gap between Donerail and the rest is massive. Here are the next four biggest longshot Derby winners after him:
Rich Strike, 2022, 80-1 Country House, 2019, 65-1 Giacomo, 2005, 50-1 Mine That Bird, 2009, 50-1Each of those winners is part of an exclusive club, and yet none of them touched 91-1. The depth of information available to today’s bettors is part of the reason. Past performance data, workout reports, and pedigree analysis are widely accessible. That kind of transparency tightens the odds across the board and makes a true 90-1 winner almost impossible to imagine.
A woman grimaces as rain falls while others watch the morning Derby workouts from the trainers and owners platform on the backside at Churchill Downs in Louisville, Kentucky. April 29, 2026The Rich Strike Run That Came Closest
If you are looking for the modern version of the Donerail story, Rich Strike is your horse. He was not even in the field until Ethereal Road scratched the day before the 2022 Derby. Trainer Eric Reed got the call with hours to spare, and jockey Sonny Leon hopped over from a full day of racing in Cincinnati to take the mount.
Rich Strike sat near the back for most of the race before slicing through traffic along the rail and overtaking favorites Epicenter and Zandon down the stretch. He won by three-quarters of a length and paid $163.60 on a two-dollar ticket. It was the second-biggest upset in Derby history and the largest in over 100 years.
Jun 8, 2022; Elmont, NY, USA; Belmont horse Rich Strike trots away from the practice track at Belmont Park Racetrack. Mandatory Credit: Jessica Alcheh-USA TODAY SportsRecent Years Have Been Kind to Underdogs
The Derby has been on a hot streak for chaos lately. Mage won at 15-1 in 2023, and Mystik Dan edged Sierra Leone by a nose at 18-1 in 2024. Compare that to the stretch from 2013 through 2018, when the favorite won six straight times. The shift has made the Derby one of the most exciting betting events on the calendar for fans of dart-throwing tickets.
So why are upsets becoming more common again? A few reasons stand out:
Larger field sizes increase traffic and trip trouble Pace scenarios often favor closers who sit off the speed Three-year-olds are still developing, which makes form less reliable Weather and track conditions can flip the script on race dayWhat This Means for Your Derby Betting Strategy
You do not need to chase 91-1 prices to find value. The point of studying Derby longshots is recognizing that the favorite is not invincible. In fact, since 2013, you have actually lost money blindly backing the chalk.
Think about how you build a ticket. A small win bet on a longshot can pay for the rest of your card. Exactas and trifectas with longshot horses on top return huge payouts when they hit. The 2005 Derby is a perfect example, where a two-dollar exacta on Giacomo and Closing Argument paid $9,814.80.
Ask yourself a few questions before you bet:
Does this horse fit the running style that wins this race? Is the jockey comfortable at Churchill Downs? Has the trainer had recent success with three-year-olds? Do the morning line odds reflect the actual chance of winning? The racetrack at Churchill Downs was muddy during early morning training for Derby and Oaks horses in Louisville, Kentucky. April 29, 2026Will Anyone Ever Top Donerail?
Probably not. The math has changed too much. Bettors have access to more data, more tools, and more sharp opinions than ever before. A horse with the kind of profile Donerail had in 1913 would likely be 30-1 or 40-1 today, not 91-1.
That is part of what makes the record so special. It captures a moment in racing history that cannot be recreated. Every May, when the field walks over for the post parade, you are watching for the next Rich Strike. The next Donerail is almost certainly never coming.
Frequently Asked Questions
How much did a two-dollar bet on Donerail pay? A two-dollar win ticket on Donerail returned $184.90 in 1913.
Who was the jockey on Donerail? Louisville native Roscoe Goose rode Donerail to victory.
Who is the second-biggest longshot to win the Kentucky Derby? Rich Strike, who won the 2022 Derby at 80-1.
Has any favorite been disqualified after winning? Yes. Maximum Security crossed the finish line first in 2019 but was disqualified for interference, giving the win to 65-1 Country House.
Responsible Gambling and Bankroll Management
Betting on the Kentucky Derby should be fun, not stressful. Set a budget before the race week starts and treat that money as entertainment expense. Once it is gone, walk away. Chasing losses is the fastest way to ruin a great day at the track.
A few simple bankroll rules can keep you in the game long term:
Never wager more than two to five percent of your bankroll on a single race Keep records of your bets so you can review what works Avoid betting under emotional swings, whether you are up or down Take breaks during long racing cardsIf gambling stops feeling like fun, reach out for help. The National Council on Problem Gambling provides free, confidential support at ncpgambling.org. 21+. Gambling problem? Call 1-800-GAMBLER. Responsible Gaming Resources
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