It’s Kentucky Derby time, and we’re ready for everything to get you fully into the race from the start.
On Saturday, the Derby will be run for the 151st time. The iconic race has seen its share of drama over all that time, including some major upsets.
Let’s take a look at some of the biggest Kentucky Derby upsets of all time, and if you feel inspired to make your own picks this weekend, check out all the Kentucky Derby odds at Bovada.
View the latest Horse Racing odds at Bovada
Animal Kingdom +2100
Not only did Animal Kingdom make his dirt debut at the 2011 Kentucky Derby, he also shocked the world with his win.
He had never raced on dirt prior to that year’s derby. But Animal Kingdom came out like a seasoned veteran, emerging from the middle of the pack to cruise to a generous 2 ¾-length win.
Not only was it Animal Kingdom’s dirt and Derby debut, but it was also the first Derby win for his trainer, Graham Motion and for his jockey, John Velazquez.
War Emblem +2100
Nine years before Animal Kingdom came from 21-1 odds, War Emblem did the same.
But his style was different, coming out of the gates hot and front-running the entire field for the duration of the race. His wire-to-wire win was the 7th-fastest Derby win at the time. Not bad for a horse that was initially purchased for a mere $20,000.
His name seemed to fit too. He was a warrior with a notoriously difficult temperament, and he drew comparisons to the star of the Black Stallion movie.
War Emblem went to win the Preakness that same year, but his Triple Crown hopes were dashed when he stumbled during the Belmont Stakes.
Thunder Gulch +2500
From an obscure trainer for the Animal Kingdom win to the famous D. Wayne Lukas, Thunder Gulch was a big upset winner at the Kentucky Derby in 1995.
This win was even more remarkable considering the powerful competition in the 1995 race. Serena’s Song was a future Hall of Famer, and Timber Country (Lukas’ other horse in the same race) had already won the Breeder’s Cup Juvenile that season and was on his way to win the Preakness Stakes.
Thunder Gulch made his name by winning at the Belmont Stakes that same season and won champion three-year-old honors.
Charismatic +3100
Another bargain find at just $62,500 when he was first purchased, Charismatic has one of the more dramatic storylines of horses that overcame their long Kentucky Derby odds.
It was just a few months before the 1999 Kentucky Derby that he was purchased, the equivalent of finding a rare sports car in the junkyard.
But then he got extremely hot, winning the Lexington Stakes and then taking the Run for the Roses (aka the Kentucky Derby itself) by a neck over Menifee, a highly-rated horse with way better odds.
He beat Menifee again just a few weeks later at the Preakness Stakes, and suddenly he was the 2-1 favorite to win at Belmont and take home the first Triple Crown in 21 years. But in that Belmont Stakes race, he suffered multiple fractures and was saved from further injury by his jockey, Chris Antley. Charismatic survived but never raced again.
Mine That Bird +5000
Every horse on this list of the biggest Kentucky Derby upsets of all time seems to have a dramatic story, and Mine That Bird is no different.
He emerged from the middle of the pack to explode past all the other horses at the 2009 Kentucky Derby. Mine That Bird won the race by over 6 lengths, the biggest margin of victory in over 60 years.
Even more incredible was that he was dead last in the race until his trainer Calvin Borel made the move to hug the rail, and Mine That Bird made a dash for glory.
If you were a Kentucky Derby betting type and laid money on Mine That Bird for that race, you probably didn’t mind that boost to your bank account. It was the second-highest payout in Derby history at the time.
Giacomo +5000
Giacomo faced improbable odds of 50-1 heading into the 2005 Derby. He did it by beating a stacked field that included legendary horses like Bellamy Road and Afleet Alex.
He had only won once before, in his maiden race, making this win even more shocking.
Of course, Giacomo did have a somewhat secret edge. He was the grandson of Seattle Slew, a Triple Crown winner and a member of the National Museum of Racing and Hall of Fame.
Seattle Slew is rated in the top 10 of the top racehorses in American racing history. It’s clear that Giacomo had some of that magic in him, and Kentucky Derby bettors today might want to dig deep on the lineage of this year’s Derby to find some potential hidden champions.
Country House +6500
With the most unconventional way to win the Kentucky Derby of all the horses on this list, Country House scored the customary 554 roses at the end of the race to take home the title.
It was the disqualification of Maximum Security, the horse who finished first initially, that allowed Country House to score a huge upset (and no doubt upsetting a few Derby betting fans who had Maximum Security on their bet slip).
It was the first time in Derby history that a horse was DQ’d for a racing infraction. Either way, Country House performed admirably but his success was short-lived. The longshot horse suffered an illness not long after the race and never raced again.
Rich Strike +8000
Just a few years ago, Rich Strike pulled off the win at the Kentucky Derby with the second-longest odds in history.
He almost didn’t even make the race, entering only as a last-minute scratch the day before opened up a spot for him. On top of his last-minute addition, he was only the second horse in Derby history to win from the 20th post position.
The 2022 Derby had one of the deepest fields in years, making Rich Strike an even bigger upset winner. (And helping his true believers strike it rich, you might say).
Donerail +9100
With the title of the longest shot to ever win the Kentucky Derby, Donerail tops our list of the biggest upsets ever. It’s also the oldest story we have in our list, going all the way back to 1913.
Most bettors ignored Donerail completely, and in fact his trainer almost didn’t enter him in the classic race. Ten Point was the heavily favored horse that day.
But Donerail truly earned his win – and maybe he had the benefit of a great warm-up – by walking the 3 miles from his stable to the Kentucky Derby track that day.
Each of these special Kentucky Derby winners proves that anything can happen on race day at the Derby, and at Bovada we’re ready for everything at the Run for the Roses too.
Sign up to Bovada today