By 1915, Winn’s Derby was the richest three-year-old racehorse event in America and seated among its Churchill Downs cognoscenti that afternoon was the complete membership of the Kentucky Racing Commission and its chairman, Hartland Farm breeder and U.S. Senator, Johnson N. Camden.

“Notables,” a local reporter wrote, “from all sections of the country were present in the greatest (40,000) gathering ever assembled at Churchill Downs.”

They would not be disappointed.

Regret, undefeated among her own sex, shattered all supposition that no filly could beat colts of the same age at a mile and a quarter in May. It took the horse (who had not raced since the previous August) and jockey Joe Notter just over two minutes (2:05 2/5) to finish their romp around the track as such tenacious but unsuccessful colts as Pebbles and Sharpshooter tried but trailed. Regret crossed her finish line first by two lengths and sent reporters racing to their typewriters.

“Behind Regret,” wrote one, “trailed the greatest field that had ever worn silk in this premier turf event.”

The long respite between races format proved less fruitful the following year when, seeking to duplicate her 1 ¼-mile Derby win in the Saratoga Handicap, Regret finished last to Stromboli. She then returned to her old self for a string of wins before ceding the 1917 Brooklyn Handicap by a nose to barn mate Borrow, and a field that included two other Derby winners and her nemesis, Stromboli.

Regret’s final race on September 25, 1917, at Aqueduct set a seven-furlong track record. She retired to Brookdale Farm on nine wins in 11 starts, having rewritten racing history as the first filly to break the Kentucky Derby’s glass ceiling.

Over the ensuing decades 15 fillies would break if not win, from Churchill Downs’ starting gates, including three Kentucky Derbies (1920, 1921, 1934) hosting more than one distaff entry.

Regret was inducted into the Racing Hall of Fame in 1957. Not so bad a ROI on a racing prospect whose Jockey Club-registered name Whitney confessed had been chosen to reflect disappointment in getting a filly rather than a colt.

The fan package included a delicious buffet breakfast at the Saratoga Race Course. It was fun to walk in before the day’s card began. I was seated near the rail and got to watch the world-class Thoroughbreds warm-up while enjoying the hot-and-cold offerings. Think piping hot scrambled eggs, savory French toast, fresh seasonal fruit, cereals, assorted muffins, Danish, yummy bacon, sausage, plus coffee, tea, and juices. (I had a mimosa at an extra charge.) I mean, why not, right? When the time came, I met others at the pickup spot out in front of the Clubhouse, and we were ready for an adventure!

We boarded an open-air trolley and took a long, leisurely ride to the James Bond Racing Stables, our guide pointing out interesting things along the way. We were excited to experience a behind-the-scenes look. Even though most of us were strangers on the trolley, we chatted as if we’d known each other for years. Some of the folks had been on the tour before, but to a different farm, while others, like me, were part of it for the first time.

I was interested in seeing where the work with horses begins, and the guide talked about this breeding farm, particularly the mystery of 007. “I read that all of the horses going to the track have a '007' saddle cloth, but that’s the extent of a connection to the actors or the movies of the same name,” one attendee said. You could hear chuckles at that. The 90-minute tour was sure to be educational, and we suspected it would be entertaining, too. 

It was obvious that everything had been done with the horse’s level of comfort in mind. From the expansive meadows where the horses run free, to the barns, where the stalls are designed for cross-ventilation to promote horse health. We were led by two women who walked and talked with us, educating the group about their breeding practices. The event was something to write home about – and certainly let us see how Thoroughbred racing supports many varied sectors of our local economy. It gave us a fantastic chance to watch remarkable animals in their earliest stages of life, there on the farm. 

Genuine Risk

Genuine Risk, Jacinto Vasquez up, after winning Kentucky Derby, Churchill Downs, May 3, 1980.
Keeneland Library Featherston Collection

Speaking of disappointment, it would be a string of 65 heartbreaks in 65 years before Kentucky Derby fans would celebrate another filly in its Churchill Downs winner’s circle.

Then Genuine Risk changed everything.

Matthew Firestone was a 14-year-old military student when he accompanied his real estate developer father, Bertram Firestone, and Bert’s third wife, Diana (a maternal cousin to actor Michael Douglas) to the July 1978 Fasig-Tipton Kentucky Yearling Sale. No tyros to Derby aspiration, since marrying in 1973 the Firestones had owned two Kentucky Derby runners-up, General Assembly and Honest Pleasure.

Young Master Firestone noticed they had dog-eared a few pages in the sales book but had overlooked a daughter by the best-known stallion of the moment, Exclusive Nation, sire of Affirmed, the Triple Crown winner crowned just a month before.

Genuine Risk - she was the first filly to finish in the money in all three Triple Crown races. In 1980 she won the Derby and finished second in both the Preakness and Belmont

Winning Colors

In 1988, Winning Colors wonthe Kentucky Derby. No filly has finished first since.
Photo: Horseracing100

While Billie Jean King inspired women’s sports, Chris Evert was having a pedigree moment.

No, not the tennis player but the eponymous Thoroughbred racehorse, who shared with “half-sister” All Rainbows the stakes-winning bloodlines that ignited like napalm on gasoline when crossed with the French sire of Canadian Triple Crown and Kentucky Derby champions, Caro.

The result was a 16.3-hand roan-grey filly that lived up to all aspirations in looks and performance: Winning Colors.

“Caro bequeathed his rugged make and a fair measure of the rather infamous disposition of his grandsire Grey Sovereign (son of the tempestuous Nasrullah) to Winning Colors, a yearling purchase [of more than half a million dollars] by trainer D. Wayne Lukas on behalf of Eugene Klein,” cited AmericanClassicPedigrees.com in an April 21, 2025, entry. “Her price reflected her size and excellent conformation as well as an excellent female family.”

Lukas wasn’t the only one with a discerning eye for a good horse. After Winning Colors broke her maiden at Saratoga by 2 ½ lengths against future Breeders Cup Juvenile Fillies winner, Epitome and four months later won in 1:09 4/5 over six furlongs at Santa Anita, Steve Davidowitz in The Best and Worst of Thoroughbred Racing recounted, “Some of the grooms and stable help who worked for Lukas made a trek to Las Vegas with one purpose in mind: to bet several hundred dollars on Winning Colors to win the 1988 Kentucky Derby at 100-1 odds.”

Chit Chat: Winning Colors and Genuine Risk are the only two fillies to compete in all three Triple Crown races: Winning Colors was third in the 1988 Preakness Stakes and sixth in the 1988 Belmont Stakes; Genuine Risk was second in both the 1980 Preakness and Belmont.

“Even today,” recalled J. Keeler Johnson in a May 20, 2025, entry for AmericasBestRacing.com, “the 1988 Derby field stands out as one of the best in history.” In addition to Winning Colors, it included Forty-Niner, Risen Star, and the unbeaten Private Terms.

“When the gates flew open, she broke like lightning, ears pinned, stride rolling, fearless from the first breath,” said jockey Gary Stevens, who used the big filly’s stride and speed to hold a four-length lead down the backstretch and into the turn.

With the approach of each challenger, he whispered to the filly, “You’re still there, girl. You’re still there.” Proper Reality came within three lengths before falling back to fourth. Seeking The Gold ran out of steam and dropped to seventh.

With a furlong to go, Winning Colors was in front and three-and-half lengths away from Derby destiny when Pat Day and Forty Niner came up the middle of the track, devouring more ground with every stride just as Stevens felt Winning Colors beginning to tire.

Stevens asked Winning Colors for one more gear one more time and she answered, holding on by a neck in a photo-finish win to become only the third filly ever to win the Kentucky Derby.

It was the first of three Derby victories for Stevens, who told The Real Players Inside the Backstretch earlier this year that winning that first one on Winning Colors was still his favorite racing moment. “It was an out-of-the-body experience.”

In 1988 Winning Colors was voted the Eclipse Award for Outstanding Three-Year-Old Filly and in 2000 was inducted into the National Museum of Racing and Hall of Fame. She is buried at Greentree Farm in Lexington, Kentucky.

The Derby’s Grandest Dames

Regret, Genuine Risk and Winning Colors broke expectations about fillies and colts without ever breaking stride. Learn more about these distaff champions and other inductees at the National Museum of Racing and Hall of Fame on Union Avenue across from Saratoga Racetrack. Visit www.racingmuseum.org to learn more.

Chit Chat: 40 fillies have run in the Kentucky Derby. No filly has competed since 2010, when Devil May Care finished tenth.