Ranking Kentucky Derby upsets
LOUISVILLE, Ky. – The 80-to-1 upset by Rich Strike in Saturday’s Kentucky Derby is undoubtedly one of the biggest shocks horse racing has seen in a long time. And the odds only tell part of the story.
Rich Strike appears to be the first Derby winner ever purchased through a claim, which is essentially a type of race where every horse is for sale at a set price and can be “claimed” by the new owner prior to post time. In this case, Rich Strike was claimed for $30,000 before his second career start last fall. Charismatic, the 1999 Derby winner, ran for a claiming tag early in his career but went unclaimed.
The horse’s owner, Rick Dawson, said Saturday he had campaigned fewer than 10 winners and had not even won an allowance race as an owner, much less a stakes. The trainer, Eric Reed, has been in the business for three decades with just one previous graded stakes winner. And the jockey, Sonny Leon, has won a lot of races at smaller tracks but never won a graded stakes.
Add in the fact that Rich Strike was on the also-eligible list until Friday morning when Ethereal Road scratched from the race and you’ve got every element of a legendary upset.
But where does it rank in Kentucky Derby history? After some reflection and research, here’s the new list of top five upsets:
1. Canonero II, 1971.
The history books show that Canonero paid just $19.40 to win, but that’s because there were only 14 individual betting units allowed at that time. So in the 1971 Derby, the six most lightly-regarded horses were clumped together as the “mutuel field,” which brought down the odds. If Canonero had been a standalone entry, he might have been at least 100to-1.
To this day, it remains the most incredible horse racing story ever: Bought in Kentucky for $1,200 as a yearling, he went to Venezuela where he had a relatively undistinguished record. But trainer Juan Arias was convinced to try the Derby after Canonero won a race against older horses and then another at Derby distance of 11⁄4 miles.
Still, the level of racing in Venezuela just does not compare to the U.S., so the horse wasn’t taken seriously at all. To top it off, Canonero’s nightmare trip to Louisville included multiple planes with mechanical issues, a quarantine paperwork mishap in Miami and a van ride to Louisville. The horse lost a lot of weight during the ordeal and looked terrible when he arrived at Churchill. But against all conventional wisdom, Canonero won – and then did it again two weeks later in the Preakness.
2. Rich Strike, 2022.
We will probably look back on Saturday’s race as the ultimate Derby fluke. No disrespect to Rich Strike or anyone associated with this wonderful story, but there is simply no conventional (or unconventional) handicapping method that would have pointed in his direction. He came into the Derby with one win in seven races, poor speed figures relative to the competition and not even a single standout performances in a stakes races that would make someone think he had the quality to win the Derby.
If they ran this same race over 100 more times, Rich Strike probably wouldn’t win it again. And yet, on the day that mattered, everything broke right for him. As sometimes happens in the Derby, the entire race was shaped by a suicidal pace on the front end: 21.78 seconds for the opening quarter and 45.36 for the half-mile. Every horse who was running close to that pace was completely cooked by the quarter-pole.
In that kind of meltdown scenario, the race slows down considerably and legweary horses end up staggering home. In fact, the second-to-last quarter was run in 26.62 seconds and the stretch run went in 25.65.
3. Mine That Bird, 2009.
Similar to Rich Strike, Mine That Bird lingered well behind the leaders for the first half of his Derby, started picking off horses around the turn with a run up the rail and then exploded in the final furlong. By the time NBC race announcer Tom Durkin actually figured out what was happening and who that was making a big move inside, Mine That Bird had already run past everyone on the way to a 63⁄4-length victory.
The difference with Rich Strike is that Mine That Bird had shown some quality as a 2-year old with four straight wins including the Grey Stakes, which is one of the most important juvenile races in Canada. After that, trainer Chip Woolley – a guy nobody in the Kentucky establishment knew anything about – took the horse to his home base in New Mexico as a 3-year old where he finished second in the Borderland Derby and fourth in the Sunland Derby. The third-longest shot in the field, Mine That Bird paid $103.20 to win on a $2 ticket.
4. Country House, 2019.
This one has a bit of an asterisk, since Country House did not cross the wire first but was elevated as the winner when Maximum Security was disqualified for veering out at the top of the stretch. It remains the only time the Derby
winner has ever been taken down by the stewards for a racing foul.
The recipient of that good fortune was Country House, who was 65-to-1 and very much deserving of those odds. After breaking his maiden in January of that year in his third start, Country House finished second in the Risen Star, a distant fourth in the Louisiana Derby and a nonthreatening third in the Arkansas Derby. The effort Country House put in on Derby Day was by far the best race he’d ever run, emerging with the lead at the top of the stretch until Maximum Security eventually wore him down.
5. Donerail, 1913.
It’s difficult to compare anything in sports from more than 100 years ago to the modern era, but Donerail remains the longest shot to win the Derby at odds of 91-to-1. One fun fact from that day is that because there were no stalls for him on the backstretch at Churchill Downs, he was housed three miles away at Douglas Park and had to walk on cobblestone streets to get to the race.
Donerail was not a bad horse. In fact, he had won some races as a 2-year old and had finished second in the Blue Grass prep race to Foundation, who was one of the Derby favorites.
So it’s not completely clear from the historical record why Donerail went off at such long odds, especially considering that there were only eight horses in the field that day.