The Most Iconic Horses to Ever Race in the Kentucky Derby

In just 32 days, Sir Barton won the Kentucky Derby, the Preakness Stakes, the Withers Stakes, and the Belmont Stakes. He won the Derby by a comfortable five lengths. Sir Barton was the first Triple Crown winner.

Gallant Fox won the Derby and would go on to win the Triple Crown, a term used officially for the first time in 1930 by The New York Times. Gallant Fox would be noteworthy as the only Triple Crown winner to sire a Triple Crown winner. That would be Omaha, who accomplished the feat in 1935.

Derby winner Omaha is the only offspring of a Triple Crown winner to also win the Triple Crown. Omaha was sired by Gallant Fox, who won the Triple Crown in 1930.

According to his lineage, War Admiral was the offspring of the legendary Man o’ War. Yet the horse had an indifferent record as a 2-year-old, winning three races in six starts. Eventually, however, War Admiral proved himself, winning the Derby by nearly two lengths, accomplishing something his storied father never did. War Admiral would go on to win the Triple Crown.

Whirlaway was dubbed “Mr. Longtail” and outdistanced the Derby field by eight lengths, a record winning margin that he shares with four other horses. It was one of four Derby victories for the team of trainer Ben Jones and jockey Eddie Arcaro. Whirlaway would go on to become the fifth 1941 Triple Crown winner.

Count Fleet was a prohibitive favorite to win the 1943 Kentucky Derby, going off at odds of 2-5 — and win he did. The horse would go on to win the Triple Crown, overcoming an injury to his hind leg. Count Fleet sired 1951 Kentucky Derby winner Count Turf.

Even though Assault wasn’t bred to race, he won the 1946 Kentucky Derby by a record eight lengths, a distinction he shares with four other Derby victors. He was also the only Texas-bred horse to have won the Triple Crown.

Citation was the last of four Derby winners for the team of Eddie Arcaro and Ben A. Jones. He raced 29 times as a 3-year-old and won 27. Citation was a prohibitive favorite to win the Derby and won the race by 3½ lengths. Winning the Triple Crown in 1948, Citation was the first horse to top $1 million in career earnings.

Secretariat thundered to horse racing immortality by winning the Derby in 1:59:40, a record that still stands. “Big Red” is one of only two horses to have covered the 1¼-mile course in less than two minutes. Secretariat would go on to win the first Triple Crown in 25 years and is considered one of the greatest horses of all time.

Seattle Slew entered the pantheon of equine greatness by becoming the only undefeated Triple Crown winner. A prohibitive favorite to win the Derby, he began his Triple Crown run by triumphing at Churchill Downs by 1¾ lengths.

The 1978 Derby champion edged out rival Alydar and would go on to win the Preakness Stakes and the Belmont Stakes to capture the Triple Crown. Seattle Slew and Affirmed are the only back-to-back Triple Crown champions.

American Pharoah would end the longest Triple Crown drought, 37 years, with his victory in 2015. In the Derby, American Pharoah’s closing quarter-mile time was faster than Secretariat’s at 24.32.

Justify began his quest for the Triple Crown with a 2½-length victory margin at Churchill Downs. After waiting 37 years for a Triple Crown champion, horse racing fans only had to wait three years for the next one, as Justify captured all three legs of the Triple Crown in 2018.

At 91-1, Donerail overcame the longest odds to win the 1913 Kentucky Derby. Many horses held the lead during the race before Donerail eventually surged ahead to win by a half-length.

Donerail paid out $184.90 for win bets, $41.20 to place, and $13.20 to show.

The victor of the 41st running of the Kentucky Derby was Regret, the first of three fillies to win the race. Regret won by two lengths. Because the race was won by a filly, that helped boost the public’s interest in horse racing.

Swaps is considered by horse racing experts as one of the greatest racehorses of all time. In the Derby, he defeated another highly regarded horse, Nashua, who would win the other two legs of the Triple Crown. Swaps didn’t run in those races because of an inflamed hoof.

Northern Dancer is considered the greatest Canadian-bred horse of all time. He won the 1964 Kentucky Derby in 2:00.00, a Derby record at the time. In Canada, Northern Dancer was considered something of a national hero. The stallion would go on to win the Preakness Stakes and finish third in the Belmont Stakes. Throughout his career, Northern Dancer won 14 of 18 races. Northern Dancer would become one of the most impactful horses in history, siring and grand-siring champion horses in the United States and Europe.

Hall of Fame jockey Willie Shoemaker at age 54 directed 17.70-1 long shot Ferdinand from last place to win the 1986 Kentucky Derby by 2¼ lengths. Ferdinand would add to his fame by upsetting Alysheba, a contender for Horse of the Year, in a photo finish at the Breeders’ Classic.

Silver Charm won trainer Bob Baffert his first Kentucky Derby in 1997. The steel-gray horse, his coat whitening with age, now lives out his retirement at Old Friends Farm. The owners of the farm say tours of the farm have doubled since Silver Charm retired there. They liken Silver Charm’s popularity to that of Elvis Presley’s because of the way he interacts with visitors.

Charismatic, a 31.30-1 underdog rallied to take the lead on the last furlong to win the 1999 Kentucky Derby. The 3-year-old then won the Preakness Stakes, and he seemed poised to win the Belmont Stakes and the Triple Crown when tragedy struck. Charismatic was leading the Belmont with a quarter-mile to go but fell back to third place. Shortly after the finish, jockey Chris Antley dismounted Charismatic, who had pulled up with what proved to be a career-ending fracture to his left front ankle. Antley persuaded the colt to lift his stricken leg, and the rider cradled the horse’s leg until help arrived. Charismatic never competed again, though he was named 1999 Horse of the Year.

Monarchos, winner of the 2001 Kentucky Derby, is in exclusive company. The horse is one of just two horses to run the Derby in under two minutes; the other is Secretariat. Nuckols Farm owner Charles Nuckols III said Monarchos, who died in 2016, was friendly and easygoing. “We ran out of guest books because so many people wanted to see him,” Nuckos told USA Today when the horse passed away.

Funny Cide, the 2003 Derby winner, is a New York-bred horse who was bought by a group of high school friends. The horse connected with horse racing fans. His popularity increased as he grew older and people came to see him in retirement. Funny Cide responds positively to fans who visit him and allows them time to photograph him. He has a website, FunnyCide.com, and a fan club.

2006 Kentucky Derby winner Barbaro shattered his right leg weeks later in the Preakness Stakes and then died of complications related to the injury. Barbaro was a Kentucky Derby fan favorite, winning all six of his starts. A bronze statue was placed over his remains at the entrance to Churchill Downs Racetrack.

Street Sense, who defeated a strong field that included Hard Spun and Curlin to win the Derby in 2007, continues his competition with Hard Spun in retirement. The two horses are retired at Jonabell Farm in Kentucky and sometimes they renew their rivalry by racing against each other.

Big Brown became the first horse to win from the 20th gate, a far outside position. He would go on to win the Preakness Stakes and looked like a strong bet to becoming the first Triple Crown winner in 30 years. During the race, however, jockey Kent Desormeaux sensed something was wrong with Big Brown’s gait and slowed the horse in the homestretch, and the horse finished last. Two weeks later, a photo showed a dislodged shoe on Big Brown’s hind leg, possibly the reason for Big Brown’s discomfort. Big Brown retired to Three Chimneys farm in Kentucky, and he is featured on daily tours there.

The gelding from New Mexico, a 50-1 longshot, shocked the horse racing world by winning the 2009 Kentucky Derby. Longtime track announcer Tom Durkin, so stunned by the victory, called the race “an impossible result.” Mine That Bird finished a length behind Preakness winner Rachel Alexandra and was third in the Belmont. Mine That Bird totaled $2,228,637 in career purse earnings and was the inspiration for the movie “50 to 1.” The horse is retired at Double Eagle Ranch in New Mexico where fans befriend him with peppermints, carrots, and apples.

California Chrome won the 2014 Kentucky Derby, becoming the fourth California-bred horse to do so. He also won the Preakness Stakes but was denied the Triple Crown at the Belmont. California Chrome’s popularity was reflected in his nickname, the “People’s Horse,” and his followers are called “Chromies.” The stallion would go on to win 16 races and amass $14,752,650 in winnings.

Alydar and Affirmed formed one of the greatest rivalries in sports and ran against each other 10 times. Affirmed edged Alydar in all three Triple Crown races in 1978. He defeated Alydar by 1½ lengths in the Kentucky Derby. Alydar retired with 14 wins in 26 starts.