Excitement is the default for every running of the Kentucky Derby. It isn’t called the “greatest two minutes in sports” for no reason. No other tent-pole event sees higher stakes play out over such a small amount of time.
Still, nothing quite gets the adrenaline flowing like a good underdog victory at the Kentucky Derby. We are not just talking about non-favorites winning the race, either. We’re talking about first-place finishes so unlikely, that online betting for the Kentucky Derby operators will have what OnlineSportsBetting.net refers to as “to be announced” odds next to their names while others receive actual lines.
Sure, investing in these horses tends to be futile. Every so often, though, a pipe dream becomes reality. All we have to do is run through some of the past Kentucky Derby winners to unearth proof.
1. Donerail Winning the 1913 Kentucky Derby
Odds: 91-to-1 (+9100)
Expectations were low for Donerail to say the least entering the 1913 Kentucky Derby. Not even the thoroughbred’s owners seemed to believe they could do more than stave off a bottom-two finish.
Well, the joke was on them. Really, the joke was on everyone.
Jockeyed by Roscoe Goose, Donerail beat the entire field, exploding past some of the favorites right out of the gate. To this day, more than a century later, this remains the longest-shot victory in Kentucky Derby history.
Frankly, it is the kind of underdog story that makes you wish social media had been around back then. Just imagine the reaction to this type of upset.
2. Rich Strike Winning the 2018 Kentucky Derby
Odds: 80-to-1 (+8000)
If you are in the market for a good Donerail proxy in the social media era, may we present you with Rick Strike’s historic Churchill Downs victory from 2022?
Indeed, the second-longest-shot to ever win the Kentucky Derby was always going to have folklore vibes to its unexpected feat. Yet, Rich Strike’s fantastical run began before they even hit the track. As the folks over at The Plaid Horse note, they weren’t even supposed to be in the race:
“Rich Strike’s victory in 2022 is a modern-day fairy tale. The horse wasn’t even supposed to race in the Derby, with trainer Eric Reed receiving a phone call just 48 hours beforethe showdown to see if his prized charge would be interested in entering the field as an alternate after Ethereal Road was scratched. The answer to that, of course, was yes, and the rest, as they say, is history. The 80-1 outsider arrived at Churchill Downs almost anonymously, with little fanfare or expectation. And nobody expected what was about to happen.
“As the crowded field came down the stretch, Rich Strike was performing admirably, sitting back in sixth place after a decent showing. Jockey Sonny Leon asked for more from the horse in a bid to push him into the places, but what he got in reply was an absolute rocket ship. Rich Strike not only kicked on, but he also powered forward almost like a car being kicked into turbo.”
Making up five spots about halfway through the race is truly insane stuff—almost as bonkers as a horse not on the card two days before the Derby winning the whole darn thing.
3. Country Horse Winning the 2019 Kentucky Derby
Odds: 65-to-1 (+6500)
The 2019 Kentucky Derby is truly a “Where were you when this happened?” moment.
While Maximum Security was initially declared the winner, Country Horse received the nod after the former was disqualified for “veering” into the runway of other races during the closing kick. Kentucky Derby officials then took almost a half-hour to examine the tape before giving the pole position to Country Horse.
What’s more, the drama did not end here. As the Associated Press later reported in 2020, Country Horse owners Mary and Gary West “sued unsuccessfully in court to have the victory reinstated and the purse money redistributed.” It would have been fascinating to see how wagers were treated if the Country Horse victory was retroactively dismissed.
It wasn’t, of course. Instead, Country Horse remains the only Kentucky Derby winner who didn’t actually cross the finish line first.
4. Mine That Bird Winning the 2009 Kentucky Derby
Odds: 50-to-1 (+5000)
Mine That Bird’s 2009 Kentucky Derby victory encapsulates just how quickly huge deficits can be erased.
Billed as not only an underdog but a total afterthought, the thoroughbred’s first two-thirds of the race unfolded as expected. Then, however, jockey Calvin Borel’s animated demeanor started surging through the inside.
In the end, Mine That Bird made up a bunch of spots over the closing kick, edging out household names and favorites such as Pioneer of the Nile and Dunkirk. Not only that, but per The Plaid Horse, it was the largest margin of victory at The Derby in “over six decades.”
5. Giacomo Winning the 2005 Kentucky Derby
Odds: 49-to-1 (+4900)
Slow and steady wins the race. Or something.
Giacomo was running true to underdog form at the start of the 2005 Kentucky Derby. Then, midway through the race, all the heavier favorites began fading out. Giacomo, on the other hand, just kept going. And going.
And going.
By the end of it all, he has galloped past everyone in the front end. He didn’t just earn the first-place nod and one of the most shocking Kentucky Derby victories ever; he incited overarching discourse on whether jockeys needed to pace their steeds more deliberately to ensure they avoided burn out before reaching the finish line.
