A recent reference question sent me on a hunt to find out if any fillies had ever won the Kentucky Derby. It turns out that three ladies have won the fabled race at Churchill Downs. The first was a chestnut mare with a white blaze named Regret who won the 1915 contest.
Regret was bred and owned by Harry Payne Whitney, a member of America’s horse racing royalty. He was the leading American owner by earnings six times between 1905 and 1930, as well as the leading American breeder from 1926 to 1932. Her trainer was James G. Rowe, Sr., a former jockey who had an illustrious second career as a trainer of racehorses. Over his career he trained more than 30 champions.
For her debut season in 1914, Regret ran in and won a series of three races at Saratoga. The first was the Saratoga Special, the second was the Sanford Memorial, and the third was the Hopeful Stakes. In all these races she ran against colts, including the season’s best juvenile colt, Pebbles, in the final two. Following this brilliant first season she was rested until the Kentucky Derby in May 1915.
At the time, the Kentucky Derby was not the iconic American race that it is today. Most of the prestigious races were based in New York. Matt Winn, the general manager of Churchill Downs, was working hard to raise the cachet of the track. In order to lure top competitors to the Derby, he decided to make it the richest race of the season. The winner’s purse was $11,450 and a gold cup. This outstripped the purses at eastern races, where the Preakness Stakes purse was $1,275 and the Belmont’s was $1,825 that year.
Regret led the field from the start and won the race by two lengths in 2:05 2/5. The sensation of a filly beating the boys, the incredible purse, and Whitney’s statement following the race that, “She has won the greatest race in America, and I am satisfied,” all combined to help launch the Kentucky Derby on the path to in fact becoming the greatest race in America. It would be 65 years until Regret had company.
Oddly enough it would be another chestnut filly with a white blaze that would finally join Regret as a lady of the Kentucky Derby. The horse that would become known as Genuine Risk was born on February 15th, 1977. At the Fasig-Tipton Kentucky July sale of yearlings 14-year-old Matthew Firestone spotted her and lobbied his parents, Bert and Diana Firestone, to purchase the filly. They agreed and Genuine Risk began schooling at the Firestone’s farm near Waterford, Virginia. She is described as generally gentle but opinionated, and was known to sometimes run off with exercise riders.
As a two year old, she began training with LeRoy Jolley and made her debut on September 30, 1978 at Belmont Park. She was undefeated in this first season of racing, and her winning streak continued into her second season. She was doing so well it was decided to test her against colts in the Wood Memorial Stakes, a race that is often a precursor to Kentucky Derby appearances. She ran the entire race just behind Plugged Nickle and Colonel Moran and finished in third, 1 and 3/4 lengths behind the boys. There was a bit of drama when her jockey claimed a foul but in the end the stewards did not agree and the results stood.
This loss cast doubt on whether running with the boys was too much for Genuine Risk and her appearance in the Kentucky Derby was doubted by many. However, she recovered well from Wood Memorial race and the Firestones, her trainer, and her jockey all felt she would be competitive in the Derby and she was entered. As the big day approached speculation abounded about all the contestants. The Lexinton Herald polled 44 members of the media and only five predicted Genuine Risk as the winner. Twenty-six of them predicted that she would finish out of the money altogether.
As it happened, she held back for the first half of the race and then moved to the outside, charged to the lead, and stayed there through the finish line where she joined Regret in a very exclusive club. After 65 years there were now two Ladies that owned the Kentucky Derby. Later Harper’s Bazaar named Genuine Risk one of its seven top women achievers for 1980.
The most recent filly to win the roses was aptly named, Winning Colors. She accomplished the feat in 1988. Like the two fillies that preceded her, she had a white blaze, but she had a roan rather than a chestnut coat. She was bred by Don Sucher at Echo Valley Horse Farm in Kentucky. At the July auction in 1986, trainer D. Wayne Lukas liked the looks of her and purchased her for an owner he represented, Eugene Klein. Lukas and his son Jeff began training her among a stable of talented horses. Her first race was at Saratoga on August 13. She won by 2 1/2 lengths over Epitome, who would go on to become the champion of the two year old filly division. She continued her racing career on the west coast of the United States winning all but one of the races she entered. On April 9th 1988 in the Santa Anita Derby, she easily led a field of 3 year old colts and won by 7 1/2 lengths. From that moment on there was no doubt that she would compete in the Kentucky Derby the following month.
On the big day at Churchill Downs she would charge to the front of the field and stay there the entire race. In an exciting finale, she was challenged in the home stretch by Forty Niner who closed a seven length lead. But Winning Colors held on to win by a neck, and joined Regret and Genuine Risk as a Lady of the Kentucky Derby.
To learn more about these wonderful fillies and their lives after the Kentucky Derby, or to brush up on your Kentucky Derby history, just drop by the Main Reading Room and I’d be happy to show you some resources.
Erica Libhart has served as the Mars Technical Services Librarian at the National Sporting Library & Museum (NSLM) since early 2016. The focus of her position is collection services, working to increase accessibility to NSLM’s collection of books, periodicals, and archival materials. The NSLM collections span over 350 years of the history of equestrian sport, as well as fly fishing, wing shooting, and other field sports. Have a question? Contact Erica by e-mail