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.

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Regret at Saratoga.  From Women of the Year by Avalyn Hunter (2004).  National Sporting Library & Museum, the gift of The Chronicle of the Horse.

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.

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Regret with trainer James Rowe (left) and owner Harry Payne Whitney (right).  From Women of the Year by Avalyn Hunter (2004).  National Sporting Library & Museum, the gift of The Chronicle of the Horse.

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.

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Genuine Risk following the Kentucky Derby.  From The Blood-Horse, May 10, 1980, pg. 2508.

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.

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Genuine Risk winning the Kentucky Derby.  From The Blood-Horse, May 10, 1980, cover.

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.

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Winning Colors.  From The Blood-Horse, May 14, 1988, Cover.

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

One of the most impressive Thoroughbred racers of the 20th Century was Gallant Fox, whose racing career lasted from 1929-1930. Gallant Fox was the second horse ever to win the American Triple Crown, and the term “Triple Crown” for the Derby, the Preakness, and the Belmont was popularized during his 1930 campaign.

“The Fox” was owned by William Woodward Sr.’s Belair Stud in Maryland but was foaled in Kentucky. Following the horse’s retirement from racing, William Woodward wrote a custom-printed memoir to commemorate Gallant Fox’s achievements. The National Sporting Library & Museum is privileged to hold a copy of this book, one of the scarcest volumes in the NSLM collection. It has great value for its memories of the entire racing career of Gallant Fox.

Gallant Fox with his dam, Marguerite. From Gallant Fox: A Memoir. National Sporting Library & Museum, gift of Mrs. Jacqueline B. Mars, Dr. Timothy J. Greenan, Mrs. Helen K. Groves, and Dr. Manuel H. Johnson, 2015.

One of Woodward’s memories of “The Fox” was his intelligence and curiosity, even from his earliest days as a colt.

The colt was broken and showed no special signs of anything one way or another, except that he was curious-minded and wanted to know all that was going on, giving every evidence of a high mentality, which however, would be slow to develop.He was a good fast colt as a yearling, with nice action, which was also the case in the beginning of his two-year-old year.

From Gallant Fox: A Memoir, by William Woodward, Sr.,
1930, National Sporting Library & Museum.

The Fox’s curiosity would last throughout his career, and it was the horse’s custom to eye the grandstands before each race. Still, Gallant Fox’s penchant for distraction led to a bad start to his racing career:

We started him in a five furlong race, with Peto as a companion. There was a good horse in the race called Desert Light. It was a small field. Gallant Fox was looking around the country when the tape was sprung and he was left about seven or eight lengths.

From Gallant Fox: A Memoir, by William Woodward, Sr.,
1930, National Sporting Library & Museum.

Despite the bad start, The Fox recovered to finish third, kicking off an auspicious career with an impressive list of prominent wins: the Kentucky Derby, the Belmont Stakes, the Preakness Stakes, the Arlington Classic, the Dwyer Stakes, the Saratoga Cup and the Jockey Club Gold Cup.

Gallant Fox’s Trainer, James E. “Sunny Jim” Fitzsimmons. From Gallant Fox: A Memoir. National Sporting Library & Museum.

The jockey for most of Gallant Fox’s wins was Earl Sande, a South Dakota native who got his start as a “bronco buster” before turning to Thoroughbred horse racing. Sande was most famous for his time on Gallant Fox, and went on to be a successful trainer and racehorse owner. Two days before the 1930 Belmont Stakes, Sande was in an automobile accident, putting his start in jeopardy.

On Thursday night before the Belmont, Sande was riding in an automobile driven by one of his friends, when they had a crash. The car turned over, and as he had been under it and was rather badly cut up, I sat with him on Friday afternoon in the Belmont paddock for quite a while to see whether he was in proper shape to ride such an important race. He was altogether himself and was fortunately unhurt except for scratches and patches. He said that his first thought, when he found himself under the car, was, “How terrible! I won’t be able to ride the horse on Saturday.”

From Gallant Fox: A Memoir, by William Woodward, Sr.,
1930, National Sporting Library & Museum.

Sande, his face bandaged from the episode, rode to victory, making Gallant Fox the second American Triple Crown winner in history.

William Woodward Leading Gallant Fox after winning the Lawrence Realization Stakes, Sande up. From Gallant Fox: A Memoir. National Sporting Library & Museum.

Later in the year, on a very heavy track, Gallant Fox lost the Travers Stakes in a major upset. Weighed down in the mud, Gallant Fox and rival Whichone dueled throughout the race, before both were overtaken by Jim Dandy, who won handily. Popular sentiment pegged Gallant Fox as weak on a heavy track. Woodward, however, saw the way the race unfolded on position as the primary reason why Gallant Fox was defeated.

To my way of thinking there were two reasons for The Fox’s defeat. First, the star was an unfortunate one for Gallant Fox. Second, he was taken wide the entire way against our will, and intentionally so, as evidenced by Workman’s ride on Questionnaire in the Realization. The Fox was horse enough to race outside of Whichone and beat him but neither he nor Whichone could give away the distance given to Jim Dandy and win.

From Gallant Fox: A Memoir, by William Woodward, Sr.,
1930, National Sporting Library & Museum.

Gallant Fox and Whichone famously lost the Travers Stakes, depicted in a series of photographic plates. From Gallant Fox: A Memoir. National Sporting Library & Museum.

Following the 1930 season, Gallant Fox was retired to stud with 11 wins in 17 races and over $300,000 in earnings.

Gallant Fox returning to the scales after winning the 1930 Kentucky Derby. From Gallant Fox: A Memoir. National Sporting Library & Museum.

Beyond racing, Gallant Fox’s enjoyed considerable success at stud. In 1932, Gallant Fox sired Omaha, who would go on to be the third winner of the American Triple Crown in 1935. In 1933, Gallant Fox sired Flares, the second American horse to win the Ascot Gold Cup, a race narrowly lost by Omaha in 1936.

From Gallant Fox: A Memoir. National Sporting Library & Museum.

Wedding Photography by Spiering Photography

John Connolly has served as the George L. Ohrstrom, Jr. Head Librarian at the National Sporting Library & Museum (NSLM) since early 2014. He is responsible for the care of the Library collections, including books, magazines, photographs, diaries, letters, and much more. 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 John by e-mail 

This coming Saturday is a big day in the horse racing world! You don’t need us to tell you that May 6 is the 143rd running of the Kentucky Derby at Churchill Downs in Louisville. The Virginia Gold Cup is also this Saturday, just down the road from us at Great Meadow in The Plains.

There are so many amazing horses, talented people, spectacular stories, and fun facts associated with both of these big events – we could never share them all. Here are just a few stories about some of the four-legged stars connected with the collections here at the NSLM.

Sea Hero
This long-shot bay colt won the Derby in 1993. Today, Sea Hero is the oldest living Kentucky Derby winner and is enjoying a life of retirement standing at stud in Turkey.

Sea Hero
Tessa Pullan (English, b. 1953), Sea Hero, 1995, bronze, on stone base, 88 x 29 ½ x 96 inches, including base, Bequest of Paul Mellon, 1999, Acquired 2014 [(c) Tessa Pullan]
One of the very few grey horses to win the Derby (only eight have ever done so), Determine won in 1954 – the same year the National Sporting Library was founded.

Man O’War
One of the most famous names in American horse racing never actually ran in the Kentucky Derby, but his progeny went on to win quite a few. The chestnut stallion’s offspring included 1937 Triple Crown winner War Admiral, and he is found in the bloodlines of most top thoroughbreds, all the way up to American Pharaoh (2015) and Nyquist (2016). Another son was steeplechaser Battleship, the first American horse to win the English Grand National Steeplechase in 1938.

Marilyn Newmark (American, 1928-2013), Man O’War, 1977, bronze, 10 ½ x 14 ¾ x 3 ½ inches, Gift of Jacqueline B. Mars, 2016.  Newmark, who is known primarily for her equestrian sculpture, created this posthumous portrait after referencing the many photographs documenting the champion thoroughbred.

Gallant Fox
Gallant Fox was the second horse to ever win the Derby, Preakness, and Belmont races (1930), and the first to be referred to as a “Triple Crown” winner by the press. Gallant Fox: A Memoir, written in 1931 by the horse’s owner, William Woodward, Sr., is one of the scarcest books ever printed by the Derrydale Press. The copy in the F. Ambrose Clark Rare Book Room here at the NSLM is numbered one of fifty (but the whereabouts of only five copies are currently recorded).

The Celebrated Horse Lexington, by Boston, out of Alice Carneal, and Churchill Downs, Derby Day, c. 1946, Published by Currier & Ives, Gift of Mrs. Parker Poe, 1978

Lexington never ran in the Derby either. In fact, he died in 1875, the first year the Kentucky Derby was run. But Lexington was the leading sire in America for decades. This print in the NSLM collection features a portrait of Lexington after Louis Maurer (German/American, 1832-1932). The portrait is surrounded by images of the first 71 Derby winners – from Aristides (1875), up through Hoop Jr. (1945).

You can see a portrait of the 1973 Triple Crown winner Secretariat, along with Derby winners Smarty Jones (2004), Barbaro (2006), and many other gorgeous thoroughbreds in our newest exhibition Andre Pater: In a Sporting Light.

Andre Pater (Polish/American, b. 1953), Secretariat, 2004, pastel on board, 20 x 24 inches, Private Collection [(c) Andre Pater]

Happy Race Day!