A big part of the excitement of the Kentucky Derby is that upsets are commonplace.
The race-time favorite of the Derby hasn’t won since 2018, and longshots are routinely draped in a garland of roses at Churchill Downs.
We have had over 150 Kentucky Derby races at this point, so when compiling a list of the top longshots, we are allowed to get picky. The pool of candidates is quite large, so this list features the longest of longshots. They are the true slim-chance kings.
Recency bias does play into this list a bit, as the field at the Kentucky Derby has increased substantially over the years. In the early 1900s, there were some years where the field had eight horses or less. These days, the field typically features 20 horses.
It’s much more difficult to pull off an upset, of course, when you have so many more competitors. But these horses did it. These are the 10 Biggest Longshots in Kentucky Derby History.
War Emblem, 2002
War Emblem’s story is an interesting one as he was sold to Prince Ahmed bin Salman’s Thoroughbred Corporation just a few weeks before the Derby. War Emblem was subsequently transferred to renowned trainer Bob Baffert, who quickly transformed the colt into a superstar. The horse earned a wire-to-wire win in the 2002 Derby despite owning 21-1 odds.
Animal Kingdom, 2011
Animal Kingdom was an afterthought heading into the 2011 Kentucky Derby as he had never raced on dirt in his career. In addition, he had a six-week layoff heading into race day at Churchill Downs, and was on his fifth rider in as many races. The H. Graham Motion-trained colt went off at 20-1 odds.
Thunder Gulch, 1995
There was simply not enough public faith in Thunder Gulch prior to the 1995 “Run for the Roses” as he went off as a 25-1 longshot. The stallion owned these long odds despite winning two of his three Kentucky Derby (G1) preps. Thunder Gulch won that year’s Big Race at Churchill Downs despite drawing Post 16, which was pretty much considered a cursed post at the time.
Charismatic, 1999
Owner Bob Lewis said he had given up on Charismatic as a winning horse in early 1999. In his last chance to prove Lewis wrong, Charismatic won the Lexington Stakes, earning a spot in the Derby. The better-late-than never Charismatic held off Menifee in the Derby to win by a head, at 31-1 odds. Charismatic wasn’t done there pulling off surprises, as the D. Wayne Lukas-trained stallion also went on to win that year’s Preakness Stakes.
Gallahadion, 1940
The story of Gallahadion at the Derby is reminiscent of David vs. Goliath with Colonel E.R. Bradley’s colt Bimelech in the role of Goliath. Bimelech raced six times in 1939 and won all six races. At the age of 2, Gallahadion started five times and never won. In fact he only finished in the money once in those five runs. But on May 4, 1940, Gallahadion (36-1 odds) edged Bimelech (5-2 odds), shocking the horse racing world.
Giacomo, 2005
Giacomo’s only win coming into the 2005 Kentucky Derby was in a maiden race at age 2. The Mike Smith horse was still in 18th place after three-quarters of a mile but eventually emerged from the pack to win by half a length, ahead of Closing Argument (another longshot at 71-1). Giacomo was trained by John Shirreffs.
Country House, 2019
On the odds alone, this is the third biggest upset in Kentucky Derby history as Country House won at 65-1. But, context is king here. Maximum Security actually crossed the finish line first but he was later disqualified (in highly controversial fashion) for “veering into the path” of another horse. The decision gave Country House a stunning victory.
Mine That Bird, 2009
Mine That Bird was painfully slow out of the gate on a sloppy track and fell far behind the pack early. Calvin Borel rode Mine That Bird into contention at the turn for home, however, and then something truly incredible happened. Mine That Bird rode the rail and looked like he was shot out of a cannon in the final 16 seconds of the race. He won by 6 3/4 lengths, which was the largest margin of victory at the Derby in more than 60 years. Mine That Bird went off at 50-1 odds.
Donerail, 1913
Donerail is the biggest longshot, in terms of longest odds, to win the Derby (91-1). That said, it was far easier to pull the wool over people’s eyes back then because the Derby was not much more than a regional race and had nowhere near the national exposure and wagering interest that it does today. Not taking anything away from Donerail, but Google “Donerail 1913 Kentucky Derby conspiracy” for a fun tale by Louisville writer Conor Shea—that may or may not be true.
Rich Strike, 2022
Rich Strike only entered the race because of a late scratch the day prior (Ethereal Road). The stallion—an 80-1 underdog entering the race—was still in 15th place after the first mile but dashed past favored Epicenter down the stretch to pull off the upset of a lifetime.
The Eric Reed-trained horse won in a field of 20 horses. Donerail (No.2 on our list) won in a field of just eight horses, which is a big reason why Rich Strike gets the edge here.
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