BH 100: Rapping at Derby's Door

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Photo: National Museum of Racing
Regret, the first filly to win the Kentucky Derby

This feature originally appeared in the August 27, 2016 issue of BloodHorse.

Fifteen 3-year-olds answered the call to the post for the inaugural Kentucky Derby in 1875. Among them were two fillies, Ascension and Gold Mine. Neither fared well, finishing 10th and last, respectively, behind H.P. McGrath’s Aristides.

Forty years came and went before the first Derby roses graced a filly’s withers. Others had rapped at the Derby door—most notably C.R. Ellison’s Lady Navarre who finished second behind Sir Huon in 1906, followed by Flamma, Gowell, and Bronzewing’s respective third-place finishes in 1912-14. Not until 1915, however, had the knocking become so persistent that someone answered.

In 1915 Harry Payne Whitney’s undefeated blaze-faced chestnut filly Regret, the 2-1 favorite, crossed the sacred threshold, handing 15 rivals a two-length drubbing. So monumental was the victory that it was mentioned in the New York Times and gave impetus to the Derby’s meteoric rise as an icon of sport.

Those days preceded the publication birth of The Blood-Horse; consequently, there is no first-hand recording of the event in its pages, but what Regret’s victory did accomplish was to open a floodgate of filly entrants. Six of the next 10 Derbys found at least one filly entered and only Viva America, third in 1918, and Prudery, third as part of Whitney’s favored entry in 1921, made the payouts.

The Blood-Horse had been a weekly magazine for six years when Calumet Farm’s Nellie Flag—like Regret a champion 2-year-old filly—started as the Derby favorite. In its reporting of her fourth-place finish behind future Triple Crown winner Omaha, Thomas B. Cromwell, editor, had this to say: “Fourth money was gained by Nellie Flag, splendid daughter of American Flag, from Warren Wright’s Calumet Farm, which was honored with popular support sufficient to make her the post favorite for the event. She might have won but for interference suffered from Plat Eye in the early stages of the race. After that she was unable to find an open way until entering the stretch. We are of the opinion that the public’s confidence was not misplaced, and we believe that this filly will before the season is much older disclose her worthiness in contests with colts.”

Nellie Flag’s missed opportunity to join Regret was one of 15 attempts in the 65 years it took for lightning to strike again.

C.V. Whitney, son of Regret’s owner H.P., had been the last to put a filly into contention in the Derby in 1959. Perhaps with an eye to upholding the family tradition, he thrust his own chestnut filly Silver Spoon, who had defeated colts in the Santa Anita Derby, into battle only to settle for fifth behind winner Tomy Lee, whom she later defeated in the Cinema Handicap in June.

For the first time in its 64 years of publication, The Blood-Horse featured a Kentucky Derby-winning filly, a blaze-faced chestnut much in the mold of her predecessor, on its cover: May 10, 1980. Editor Kent Hollingsworth’s “What’s Going On Here” column paid tribute to the past as well as to the present: “The fair sex has been conspicuous at the Kentucky Derby (gr. I) for many years, never before to the extent of coming down 1-2-3 as winner, owner, and breeder…” as filly winner Genuine Risk joined winning owner, Mrs. Bert Firestone and breeder, Mrs. Sally Humphrey to constitute a one-of-a-kind Trifecta.

A special event demands special coverage, and The Blood-Horse complied in managing editor Ed Bowen’s feature that paid homage to 1915 with the title “This Risk Brought No Regrets” and a paragraph that framed the momentousness of the accomplishment: “Thus was born a dream not looked upon as impossible inasmuch as it had precedent, but one which was lacking in reinforcement for more than six decades. The dream was that maybe here was a filly which could be aimed for the Kentucky Derby (gr. I) rather than the Kentucky Oaks (gr. I) or other filly races. Regret had won the Derby in 1915, helping vault the race into national prominence, and Regret had been a singular figure since then. Maybe Genuine Risk could join the most exclusive sorority in racing.”

While Genuine Risk might not have been the favorite in the betting, she ran like one as the daughter of Exclusive Native—Virtuous, by Gallant Man, defeated a solid field of 12 males by one length.

Racing didn’t have to wait another six generations for another filly to become part of a triumvirate. A comparatively short eight years later the May 14, 1988, cover of The Blood-Horse announced “The Lady Is a Winner,” superimposed on a photo of a roan Winning Colors bettering a battling Forty Niner by a neck with 15 rivals strung out behind them.

So, twice within nine years a filly had worn the roses. Comparatively speaking, it was getting to be a matter of old hat, but Bowen, then editor-in-chief, drew reference to the past: “The lure of a filly attempting to follow only Regret (1915) and Genuine Risk (1980) as distaff Derby winners very nearly made Winning Colors the favorite. Late in the betting, Private Terms edged by her…” It was indeed a matter of a few dollars as both went off at 3-1 on the tote board.

Like Regret and Genuine Risk before here, Eugene Klein’s daughter of Caro—All Rainbows, by Bold Hour, also earned honors as champion 3-year-old filly. In the 28 years since Winning Colors’ victory, only five other fillies have attempted the feat with the ill-fated Eight Belles’ runner-up finish in 2008 coming closest.

Read more BloodHorse 100 features here.