Next year, we will honor the centennial anniversary of Regret’s history-making victory in the Kentucky Derby. Colonel Matt Winn, president of Churchill Downs, later said that the filly’s win “made the Kentucky Derby an American institution.” Two others followed, though many years later: Genuine Risk in 1980 and Winning Colors in 1988. These three make up an unforgettable trifecta of names in Derby history books.
One year after Regret’s triumph, Fifinella won England’s prestigious Derby Stakes. Fifinella was one of six females to defeat their male counterparts in the “Blue Riband” of racing, an event run annually since 1780, and, as we are about to step into 2015, no other filly since has achieved that feat. Fillies these days, even the exceptional ones, choose the Oaks as a target and wait for future events down the line to tackle colts.
The Oaks and Derby are traditionally run the same weekend, but that didn’t stop Eleanor from winning them both anyway. Bred by the notable Sir Charles Bunbury, president of the first Jockey Club, Eleanor was from a strong family of winners and producers and did a fine job of emulating her relatives on the racetrack. In 1809, she became the first filly to win the Derby, beating ten others, then defeated five fillies to take the Oaks for her own as well.
Eleanor ran until age seven, then was retired to stud for Bunbury. Her best offspring was two-time leading sire Muley. His father? Orville, whom Eleanor once got the better of on the racetrack.
After Eleanor’s Derby success, other fillies took a stab at the colts at Epsom Downs, but were none successful until nearly a half-century later, when Blink Bonny came home victorious in 1857. Sired by Melbourne, whose son West Australian had become the first horse to win the English Triple Crown four years previous, Blink Bonny, like Eleanor, completed the Derby-Oaks double, though the two efforts could not have been more different: her Derby win by a neck in a blanket finish, the Oaks by a dominant eight lengths.
Blink Bonny retired after two races at four and produced Blair Athol, who was described by bloodstock expert William Allison as “the best horse I have ever seen, the best bred, best looking, and he beat the best Derby field ever seen, and that too in his first race.” Blair Athol won the Triple Crown in 1864, and, after his racing days, became a four-time leading sire.
Time passed, and descendants of both Eleanor and Blink Bonny were enjoying success on the track when chestnut filly Shotover came onto the scene in 1882. Not only did she defeat colts in the Derby, she handed them defeat in the Two Thousand Guineas as well. She rose to further success in the breeding shed as the third dam of Frizette, ancestress of legends like Seattle Slew and Mr. Prospector.
The 19th century ended with three fillies victorious in the Derby. Three more would follow in the new millennium, though this time, their stars would emerge in the span of just eight years.
In 1904, a prized mare and an underachieving stallion thought to be “in love” by Italian breeder Cavaliere Edoardo Ginistrelli were mated and, almost a year later, produced a filly the owner named Signorinetta (story from The Biographical Encyclopedia of British Flat Racing by Mortimer, Onslow, and Willett). After winning just one race in seven starts, Signorinetta was entered in the prestigious Derby and went off at odds of 100-1 – a hopeless longshot against seventeen other colts. Hopeless? Signorinetta knew not that word. She drew off to win by two lengths, shocking the large crowd assembled. Two days later, she added the Oaks to her resume as well.
Ginistrelli, thought by some as an eccentric, sold the filly to Lord Rosebery for money to return to his home country, Italy. Signorinetta produced winners from a handful of foals and died 20 years after her famous Derby victory.
Four years after Signorinetta’s Derby shocker, the great sire Cyllene sired his last British classic winner when Tagalie came home a winner by four lengths in the Derby. It was to be her finest achievement – she never won another race and was a disappointment in the breeding shed.
And then there was one. The feisty Fifinella has already been mentioned. Described by her owner as “catty and peevish,” she had a tendency to run erratically, including in the Derby, where she had just enough heart to get up over well-bred Kwang-su by a neck. Very soon after that, she became the fourth filly to complete the Derby-Oaks double. She retired after a third-place finish to future legendary sire Phalaris and retired to stud. Many of her offspring were doomed from the start, for they inherited her temper.
Gone are the days when horses make close consecutive starts. Fillies winning both the Derby and Oaks in the same weekend are a thing of the past. After Fifinella’s win, only one female was able to hit the board in the Derby: Nobiliary, who finished second to Grundy in 1975.
That’s not to say fillies don’t defeat males anymore – recent names like Zenyatta, Gentildonna, and Treve put a swift end to that line of reasoning. But the days of them doing so in the prestigious Derby Stakes are nearly a century behind us, and we can only venture a guess as to when the seventh female winner will come about.