A Score of Kentucky Derby Winners! Quiz

The very first winner of the Kentucky was the chestnut colt Aristides. Standing at 15¾ hands, he was sired by the great English colt Leamington. Aristides was named not for the ancient Greek statesman but for Pennsylvanian breeder Aristides J. Welch, who had brought Leamington the USA. The formerly enslaved Ansel Williamson (1806-1881) trained Aristides--and many other champions besides.

Aristides, not added to the startup until the morning of the race, was supposed to be a "rabbit" for the favored Chesapeake in the 1st Kentucky Derby, meaning he was supposed to lead the pack and wear out the other horses so that Chesapeake could come from behind. But Chesapeake gave out, so jockey Oliver Lewis took his diminutive colt to victory, one length over runner-up Volcano.

The prize for the 1st Derby was a thousand-dollar silver punch bowl. Aristides' time of 2:37¾ set a record for a 3-year-old Thoroughbred at 12 furlongs (1½ miles). In 1988 Churchill Downs launched the Aristides Stakes for horses aged 3 and up.

A large, light-chestnut gelding, Apollo was bred by Daniel Swigert, breeder of the previous Derby winner, Hindoo. Runnymeade was a heavy favorite in the 8th Kentucky Derby. He was in third place at the one-mile post, and by the home stretch he was in the lead. But then, in the last furlong, Apollo rushed in and beat Runymeade by half a length!

Apollo did not race at age 2 because of injuries. For over a century, until Justify's victory in 2018, no other horse who was unraced at age 2 was able to win the Kentucky Derby, leading to the urban legend of the "Curse of Apollo". Sadly, Apollo was over-raced at ages 3 and 4, and by age 5 or so he had retired to be a saddle horse in Charleston. Aristides died of tetanus in 1887.

Kingman's slowness record is monumental. The Kentucky Derby in 1891 was still at 12 furlongs (1½ miles), but it was reduced to 10 furlongs (1¼ miles) in 1896, so the record will stand.

Indeed the whole Derby was so slow that the newspaper "Spirit of the Times" called it "simply a canter, not even a respectable gallop, each jockey apparently having orders to stay in the rear and let the others cut out the work". In fact, one of Kingman's owners had instructed jockey Isaac Murphy to "walk, if [competitor] Balgowan walked", according to the "Courier-Journal". But when Balgowan began to run in the last quarter-mile, Murphy let Kingman loose to win by a length.

The 1891 Derby is also remarkable for having one of the smallest starting fields -- just 4 horses -- because major Eastern owners considered the Kentucky Derby not yet prestigious enough to risk racing their 3-year-olds so early in the season.

Kingman was trained by one of the last African-Americans to produce a Derby winner, Dudley Allen, emancipated from slavery when he enlisted in the U.S. Civil War. The bay racehorse showed a lot of promise as a 3-year-old, yet despite winning the 17th Derby, it did not materialize. Nor was Kingman a successful stud, and he quietly passed away at age 5.

Donerail's run in the 39th Kentucky Derby was remarkable for a couple of reasons. First, with jockey Roscoe Goose set a new track record at Churchill Downs with his time of 2:04? for 10 furlongs. Second, Donerail set the record for the longest odds of a Derby winner, which at a whopping 91-1 paid $184.90 on the minimum $2 bet!

One more item of note: Thomas P. Hayes bred, owned, and trained Donerail. He was the second person to do all three for a Derby winner, the first being Maj. Thomas C. McDowell for Alan-a-Dale (1902).

The big-boned bay was named for a flag station on the Queen & Crescent Railway in Kentucky. During World War I, Hayes donated Donerail to the Army Remount Service in December 1917. The stallion returned to racing briefly in 1918 at age 8. It is not known when the champion horse died.

Old Rosebud ran the middle of three consecutive races that took the Kentucky Derby to national prominence -- the first being the odds-busting Donerail and the third being the Amazonian filly Regret. Old Rosebud gained recognition for setting two Derby records in the 1914 race: first, his time was 2:03-2/5, which stood for 23 years until surpassed by War Admiral in 1937. Second, his margin of victory was 8 lengths, a record tied but not broken since.

The only Texas-bred horse to win the Derby, Old Rosebud was a small, bay gelding with a sharp mind but a swayed back and flattened knees that led to lifelong tendon issues. At times he had to be trained while hitched to a cart to protect his tendons from the weight of a rider! He had multiple breakdowns in his career yet returned to racing again and again, earning the nickname the Comeback Kid. Finally in 1922, he suffered a fatal injury Jamaica Race Course in Queens, New York during a claiming race.

In 1915, the 15th filly to start in the Derby defeated 15 male rivals! The statuesque Regret became the first filly to win the Run for the Roses. Two other fillies challenged her in the 41st Kentucky Derby: Prudery and Nellie Flag.

Respiratory ailments prevented Regret from racing in the Kentucky Oaks, a fillies-only contest considered to be the sister race to the Kentucky Derby, on May 21. If she had raced in it, she might have become the only Derby-Oaks dual winner; the Oaks is now held on the day before the Derby, and the required prep races for each differ significantly.

Regret raced through 1917 and then became a broodmare during the next couple of decades. Three days after bearing her last foal, she died in Kentucky of internal bleeding in 1934.

The winner of the 50th Kentucky Derby became quite the subject of popular attention in midcentury America. The movie "Black Gold" (1947) was very loosely based on the colt; the only real connection was the fictional colt's name and the Native-American ancestry of the owner (played by Mexican-American Anthony Quinn). Marguerite Henry wrote a best-selling book about him in 1957, though much of it was fictionalized.

Black Gold was the second Kentucky Derby winner to be bred by a woman and owned by a woman, Rosa Hoots, who also happened to be of Osage descent. Black Gold was also the first Derby winner to receive a golden trophy. Black Gold won three other Derbies in 1924, a record not duplicated by another Kentucky Derby winner until California Chrome (2014).

Unfortunately, Black Gold suffered many injuries.Sadly, he had to be euthanized when he broke his leg in 1928. In that last race, he was said to have finished "on three legs and a heart".

The son of the great Man o' War, War Admiral set the pace and won the 63rd Kentucky Derby handily in 1937. He went on to win the Preakness Stakes and the Belmont Stakes to become the 4th winner of the Triple Crown in 1937. Yet he might be better known in popular culture for losing a 1938 match race against underdog Seabiscuit.

War Admiral's broodmare line produced several Triple Crown winners: Seattle Slew, Affirmed, American Pharaoh, and Justify. The racing greats Cigar and Zenyatta are also descendants of War Admiral.

Known as "Mr. Longtail" and "Whirly," for his exceptional tail, the chestnut colt Whirlaway set a new new track record for Churchill Downs with his time 2:01? at the 67th Kentucky Derby. He went on to be the 5th horse to win the Triple Crown, and the first of an amazing quartet of horses to achieve the honor in the 1940s.

Whirlaway was also the first of an astonishing eight Kentucky Derby winners and eight Preakness Stakes winners bred and owned by Calumet Farm. He was only horse to have won both the Triple Crown and the Travers Stakes, the original "Grand Slam" or "quadrufecta" of U.S. horseracing.

During WWII, Whirlaway raised $5 million in war bonds. After a respectable breeding career, Whirlaway died of a heart attack in 1953.

The winner of the 1958 Kentucky Derby, Tim Tam was one of eight Derby and eight Preakness Stakes winners produced by Calumet Farm. Tim Tam won the Derby and the Preakness, but in the Belmont Stakes, as he headed down the home stretch, he fractured a seismoid bone and limped over the finish line in second place. Superstitious racing fans like to point out that the Belmont Stakes was Tim Tam's 13th race that year.

Tim Tam recovered from the injury, however, thanks to the work of Dr. Jacques Jenny's team at the University of Pennsylvania's veterinary school. Though he could never race again, he lived a long life as a stud at Calumet Farm. Arnott's Biscuits introduced their Tim Tam chocolate biscuit in Australia in 1964 in honor of the dark bay stallion.

Northern Dancer was the first Canadian horse to win the Kentucky Derby. He was the grandson of the celebrated Native Dancer, known as the "Gray Ghost", who suffered his one and only career defeat in the 1953 Kentucky Derby.

Northern Dancer was also known for his progeny. He sired Nijinsky, considered one of the greatest Epsom Derby winners. He also sired Dancer's Image, who won the 1968 Kentucky Derby but due to a drugs violation, was denied the purse, which went to Forward Pass*.

*Forward Pass is often listed as the "official" winner. According to Kentucky's laws and regulations at the time, drugs disqualified a horse from winning the purse but not winning the race itself. In fact, Churchill Downs in 1968 paid off "win" bets to those who bet on Dancer's Image. The incident was still in dispute by the descendants of the owners and trainers in question in the early 21st century.

Handsome, colossal, and swift, Secretariat is regarded as one of the greatest Thoroughbreds in history. "Big Red" won the 1973 Kentucky Derby handily and became the ninth horse to win the Triple Crown, and the first to do so in 25 years. He was also the first of a trio of Triple Crown winners in the 1970s.

His win in Kentucky Derby set the record for the fastest time at 1:59-2/5. He accelerated completely through the race, completing each quarter faster than the one before. He won the Belmont Stakes with a world record of 2:24 on 12 furlongs (1½ miles) on *any* dirt track, with a mind-blowing 31-length margin!

Secretariat stood 16¾ hands tall (that's 64¾ inches or 164.5 cm), and his stride was an amazing 24 feet, 11 inches. As beautiful as he was fast, he lacked *any* major flaws in conformation. His primary owner, Penny Chenery of Meadow Stable, the daughter of breeders and a divorcée, was one of the few women owners and breeders in U.S. horseracing at the time who made international fame. She had to hire the Willam Morris Agency to handle Secretariat's public appearances. The photogenic Secretariat appeared on the covers of "Time", "Newsweek", and "Sports Illustrated".

Secretariat developed laminitis in 1989 and had to be put down, but not before he sired a number of daughters who in turn bore such notable racehorses at A.P. Indy and Storm Cat.

A chestnut colt and descendant of War Admiral, Affirmed was the last of a trio of Triple Crown winners in the 1970s (the prior winners being Secretariat in 1973 and Seattle Slew in 1977), as well as the last Triple Crown winner of 20th century.

With his win the 104th Derby, Affirmed became the youngest horse to earn $1 million. The following year, in 1979, he became the youngest to reach $2 million with the Jockey Club Gold Cup. Jockey Steve Cauthen also became he youngest jockey ever to ride a Derby or Triple Crown winner.

Affirmed was also famous for his rivalry with Alydar, who came a close runner-up to Affirmed in each race of the Triple Crown. Affirmed was so named because co-owner Louis Wolfson of Harbor View Farm believed that despite a securities fraud conviction, his innocence would one day be affirmed. Or so his wife Patrice Wolfson claimed once in an interview.

Like Secretariat before him, Affirmed had to be euthanized for laminitis in 2001. Unusually for a racehorse, Affirmed was interred whole, wearing the silks of his original owner, Harbor View Farm.

As the "middle child" of the three fillies who won the Kentucky Derby, Genuine Risk often gets the least historical attention. Yet the big chestnut horse had an impressive record in 1980, when she won Eclipse Award as the American champion 3-year-old filly. She was the first filly to even race in the Kentucky Derby since Silver Spoon in 1959. Genuine Risk was also the first filly to complete in all the American Classic races for the Triple Crown.

With high hopes, Genuine Risk was mated to the great Secretariat, but the foal was stillborn, and she suffered reproductive damage. In all, the champion mare produced only two offspring, both unraced colts, but their births prompted fans to shower "Genny" with carrots, plush toys, and artwork. The younger colt was gelded and became a show horse. The elder colt, Genuine Reward, was rescued from sale to a possible kill-buyer by Laura Hillenbrand, author of the 2001 best-seller "Seabiscuit". He sired some polo ponies and spent his last years comfortably at the Old Friends Retirement Facility in Kentucky.

The last of three fillies to win the Kentucky Derby in the 20th century, Winning Colors was also the second filly to compete in all three Triple Crown races. Colored gray or roan, depending on whom you ask, she was ridden by the famed jockey Gary Stevens in the 114th Derby. That same year she earned the 1988 Eclipse Award for Outstanding 3-Year-Old Filly.

Kentucky-bred Winning Colors was quite aggressive for a filly, though, and difficult to handle at times. She raced as a 4-year-old and then retired as a broodmare. She had to be put down after getting colic in 2008.

Kentucky-bred Monarchos overall had a brief racing career because of a ruptured tendon and only a passable stud career, but during his brief time in the sun he gained fame for a few reasons.

Crossing the line at 1:59.97, Monarchos was the second horse to win the Derby in under 2 minutes, the first being the great Secretariat in 1973. Monarchos was the *third* horse, however, to *complete* the Derby in under 2 minutes, for the runner-up in the 1973 Derby, Sham, finished with an estimated time of 1:59.8 -- estimated because the official clock was stopped once Secretariat crossed the line. No other Derby starters in the 19th or 20th centuries broke the 2-minute barrier.

Monarchos was also part of the select "club" of horses who won the Derby and grueling Belmont Stakes, but lost the shortest race of the Triple Crown, the Preakness Stakes at Pimlico.

Monarchos was also only the 7th gray horse to win the Kentucky Derby (most Thoroughbreds fall into brown, chestnut, or bay classifications of coat color). His nickname in the stable was "Sparky". He succumbed to a ruptured intestine in 2016.

The bay colt Barbaro was a celebrated racehorse whose promising career was cut short by a catastrophic injury. His winning time of 2:01.36 in the 132nd Derby, while good, was not spectacular, but he had already shown that he could excel on both turf and dirt, which is uncommon for a Thoroughbred (it's usually one or the other).

During the 2006 Preakness, however, he broke his right hind leg in 20 places, and his foot dangled loosely. He was flown to the University of Pennsylvania for surgery that included fastening 27 screws into a locking compression plate. He seemed to be recovering, but then he developed laminitis, which normally leads to euthanasia; however, a special boot kept him alive. News media covered Barbaro's story as they might for a political figure or a movie star, and Dr. Dean Richardson, chief of Large Animal Surgery at Penn, was struck by the positive attitude and grace of his patient. Alas, further complications set in, and the brave colt had to be humanely destroyed.

Fans grateful for the work at Penn donated enough money to start the Barbaro Fund and the Laminitis Fund for care of large animals. Barbaro's monument graces the entrance to Churchill Downs, where he has been laid to rest and where he may be visited by mourners without having to pay admission.

Most entrants in the Kentucky Derby arrive by plane or fancy horse vans and boast impressive wins in Grade I stakes. The diminutive Mine That Bird, however, rode 1,500 miles from New Mexico to Churchill Downs in a trailer attached to a pickup truck driven by trainer Chip Woolley. Furthermore, his entry outraged some owners because at the time, the entries were determined by total graded stakes wins, and he had also lost two races recently, had shifted owners frequently, and had never won a Grade I stakes race.

At 50-1 odds and only 15.3 hands (5'3" or 160 cm) Mine That Bird was not expected to win. Nevertheless, veteran jockey Calvin Borel managed to squeeze little Mine That Bird in tightly along the rail, beneath the notice of the track announcer who was focused on bottleneck among Pioneerof the Nile, Musket Man, and Papa Clem. Mine That Bird was three lengths ahead before veteran announcer Tom Durkin spied him! At the time of his victory, Mine That Bird was tied with Giacomo for having the second-longest odds. His story was immortalized in the movie "50 to 1" (2014), with Borel playing himself.

Because he clocked unimpressive times in the Kentucky Derby and Preakness Stakes, some thought at first that American Pharoah might just be the "best of a bad lot". He showed his mettle, however, by winning the Belmont Stakes with a time of 2:26.54, which was the second-fastest for a Triple Crown winner (behind only Secretariat's 2:24). With that, American Pharoah became the first U.S. Triple Crown winner in 37 years!

Additionally, American Pharoah was the first ever to win a newly-coined "Grand Slam" consisting of the three American Classics plus the Breeders' Cup Classic, and he did so with a track record at Keeneland of 2:00.07 for 10 furlongs (1¼ miles). He did not, however, win the original (and some think nigh impossible) Grand Slam or Superfecta consisting of the Triple Crown plus the Travers Stakes at Saratoga Springs, a track known as the "graveyard of champions". Only Gallant Fox (1930) has ever accomplished this.

American Pharoah was named, misspelling of "pharaoh" and all, in a contest sponsored by owner Ahmed Zayat. He was an enormously popular horse, and "Pharoah's Phans" would attend races dressed in ancient Egyptian costumes. Both "The Blood-Horse" and "Thoroughbred Daily News" named him Horse of the Decade.

The large bay colt Justify was the second Triple Crown winner of the 21st century, and the final such winner in the 2010s. He is also noted for breaking the Curse of Apollo by being only the second horse ever to win the Derby after not racing at all as a 2-year-old, as Apollo did way back in 1882.

In fact, in 2018 he had become the most lightly raced Triple Crown winner yet, for the Belmont Stakes was not only his sixth but also his last start. Justify's jockey, Mike Smith, became at age 52 the oldest jockey ever to win the Triple Crown as well. Justify also made his trainer Bob Baffert the second person ever to train two Triple Crown winners. The first was "Sunny Jim" Fitzsimmons, who trained father-and-son Triple Crown champions Gallant Fox (1930) and Omaha (1935).