Santa Anita Late Daily Double
Oaks Winners in the 3-year-old Classics
Rachel Alexandra winning the 2009 Preakness
2009 Oaks winner Rachel Alexandra beating 2009 Derby winner Mine That Bird in the Preakness (Eclipse Sportswire)

In recent years, Kentucky Oaks winners have gone on to successfully challenge their male peers in the classic 3-year-old races–Rags to Riches won the 2007 Belmont Stakes over Preakness Stakes winner Curlin, and Rachel Alexandra defeated Kentucky Derby winner Mine That Bird in the 2009 Preakness Stakes. The public generally perceives such occasions as exceptional, and, with the rising number of and higher purses for restricted filly races, that perception is generally true as owners have little financial motive for pursing the tougher open company events. However, this wasn’t always the case. In fact, history is resplendent with top 3-year-old fillies, and specifically Oaks winners, who have performed exceedingly well in open company during their 3-year-old campaigns.

Not many may remember Pike Place Dancer’s victory in the Grade 3 California Derby against males before her victory in the 1996 Oaks, or Cicada’s runner-up effort (by a nose) against Ridan in the 1962 Florida Derby before her Oaks win. Before she won the 1957 Oaks, Lori-El finished third in the Arkansas Derby against colts. Filly runners in open company races appear to be anomalies, and, in many ways, they are. However, the farther back one looks, the more numerous examples exist where Kentucky Oaks winners regularly challenged male competitors, particularly in the classics.

The Classics:
What exactly are the historic “classic” American thoroughbred races for 3-year-olds? According to Thoroughbred Heritage, the Kentucky Oaks, Alabama Stakes, Coaching Club American Oaks, and Mother Goose Stakes are the Classics restricted to fillies, while the open-company races are the Kentucky Derby, Preakness Stakes and Belmont Stakes, which form the Triple Crown, as well as the Travers Stakes, Withers Stakes and the now-defunct Lawrence Realization Stakes.

Listed by inauguration date and name:
1872 Alabama Stakes
1867 Belmont Stakes
1917 Coaching Club American Oaks
1875 Kentucky Derby
1875 Kentucky Oaks
1889 Lawrence Realization Stakes
1957 Mother Goose Stakes
1873 Preakness Stakes
1864 Travers Stakes
1874 Withers Stakes

The second-oldest classic and the race later recognized as the final leg of the Triple Crown, the Belmont Stakes was actually won in its inaugural running by a filly, Ruthless, one of the so-called “Barbarous Battalion” of full sisters out of the great mare Barbarity. Ruthless also won the oldest classic, the Travers, the second filly to do so after the 1865 edition was actually swept by three fillies, the victress Maiden, followed by runner-up Oleata and third-place finisher Sarah K. In all, seven fillies have won the Travers (colloquially referred to as the Mid-Summer Derby), the last being Lady Rotha in 1915.

In addition to Ruthless and Rags to Riches, the other filly to win the Belmont Stakes, Tanya in 1905, skipped the Kentucky Oaks, but followed up her Belmont victory with a narrow second-place finish to the once-beaten colt Sysonby in the Lawrence Realization Stakes.

While Rachel Alexandra’s winning the 2009 Preakness over Kentucky Derby winner Mine That Bird was historic, it wasn’t the first time a filly had won the race. Previous female winners include Flocarline (1903), Whimsical (1906), Rhine Maiden (1915) and Nellie Morse (1924). Additionally, Kentucky Derby winners Genuine Risk and Winning Colors went on to finish second and third respectively in their Preakness attempts. 1930 Coaching Club American Oaks winner Snowflake finished third in the Preakness behind eventual Triple Crown winner Gallant Fox.

Three fillies have won the Kentucky Derby-Regret (1915), Genuine Risk (1980) and Winning Colors (1988)—but a number of others have finished second, most recently Eight Belles (2008). Because the Oaks is now run one day prior to the Derby, Oaks winners are not likely to run back in the Derby. However, that was not always the case; Lady Navarre finished second to Sir Huon in the 1906 Derby; she repeated that runner-up performance against Sir Huon in the Latonia Derby and behind Kings Daughter in the Oaks.

A Golden Age of Fillies: The 1910s
In the 1910s, the Kentucky Oaks marked the close of the Churchill Downs meet, and thus was run a few weeks after the Kentucky Derby. Fillies of considerable talent often challenged colts and geldings head on, such as Flamma who finished third of seven starters, five lengths behind winner Worth, over a muddy Churchill track in the 1912 Kentucky Derby; seventeen days later she won the Kentucky Oaks over another off-track.

In 1913, Gowell finished third in the Derby, two lengths behind 91-1 longshot Donerail, who set a new track record in the effort. Exactly one week later, she won a virtual match race in the mud versus the colt Leochares at Churchill, but she failed as the Kentucky Oaks favorite only seven days later, finishing third and reportedly sore from her previous races. However, on June 14, Gowell did become the second filly to win the 1-1/2 mile Latonia Derby, once a benchmark 3-year-old race, but last run in 1937.

While it seems out of character (and, to today’s horse racing fans, improbable), running back so quickly off their last effort was once commonplace for American Thoroughbreds. Take the filly Bronzewing, for example. In 1914, within the space of one month, she won the Ashland Oaks and Blue Grass Stakes (the latter over males) before finishing a distant third to Old Rosebud in the Derby, but then rebounded 13 days later to win the Kentucky Oaks after a brilliant stretch run.

In 1915, Regret became the first filly to win the Kentucky Derby, but she didn’t even run in the Oaks after scratching from the race ultimately won by the talented Waterblossom, later winner of the Alabama Stakes. The Oaks third-place finisher that year, Lady Rotha, went on to win the Travers against males.

After taking the early lead, Viva America faded to third in the 1918 Kentucky Derby won by the legendary gelding Exterminator. Fourteen days later she won the Kentucky Oaks.

The Roaring ’20s
A number of Kentucky Oaks winners or place getters in the 1920s performed admirably running against their male counterparts, beginning with 1921 Oaks runner-up Prudery, whose May 14 loss by a scant head to Nancy Lee was a mere week after she had finished third in the Kentucky Derby to Behave Yourself. Later that summer Prudery won the Alabama before finishing second in the Travers to Belmont runner-up Sporting Blood.

1923 Oaks winner Untidy finished second to Derby and Belmont winner Zev in the Lawrence Realization, and even took on older males, running second to champion Little Chief in Metropolitan Handicap. The following year, Nellie Morse followed up her victory in the 1924 Preakness with a second-place finish in the Kentucky Oaks, a race that she might have won if not for significant interference by disqualified winner Glide while the elevated winner Princess Doreen ran unimpeded.

Other key fillies of the 1920s include 1926 Oaks winner Black Maria, who took the Aqueduct Handicap (now the Evening Attire) against older males and finished third in the prestigious American Derby. Nimba skipped the 1927 Oaks, but won not only the Alabama and Coaching Club American Oaks, but also the Lawrence Realization, and then finished second in the Travers. 1928 Oaks victress Easter Stockings finished second against males in the Ohio Derby.

The 1930s and Beyond:
Beginning in 1930, American racing entered into a “Golden Age” that saw a string of extraordinary 3-year-old colts win the Triple Crown: Gallant Fox (1930), Omaha (1935), War Admiral (1937), Whirlaway (1941), Count Fleet (1943), Assault (1946) and Citation (1948). I suspect that it was in this era that attitudes about running 3-year-old fillies in open company races began to change.

While fewer Oaks fillies contested the open company classics, they still enjoyed significant success against their male counterparts. After her 1935 Oaks win, Paradisical won the Ohio Derby, while 1934 Oaks victress Fiji later took the Latonia Derby. Before her 1937 Oaks win, Mars Shield won the Texas Derby over the talented Heelfly in near-track record time; her connections chose not to run her in the Kentucky Derby, won that year by Triple Crown victor War Admiral. 1933 Oaks winner Barn Swallow was runner-up to Sun Archer in the open-company Potomac Handicap.

Another filly worth mentioning that did not run in the Oaks but that won major open company races is Good Gamble, who finished second to Triple Crown winner Omaha in the 1935 Dwyer Stakes and who won the Potomac and Aqueduct Handicaps over the talented Count Arthur. And how about Nellie Morse’s daughter Nellie Flag, who ran fourth in the 1935 Kentucky Derby? As good as Good Gamble, Nellie Flag and Paradisical were, they were all beaten out for champion 3-year-old filly honors by Black Helen, winner of the Coaching Club American Oaks who also defeated colts in both the Florida Derby and the American Derby.

Between 1937 and 1979, only two fillies even attempted to run in the Kentucky Derby. The totally outclassed Misweet finished twelfth in 1945 when the race was run in early June rather than on its historic May date. In 1959, a very talented daughter of Triple Crown winner Citation named Silver Spoon entered after becoming only the second filly to win the Santa Anita Derby (the first was 1939 victress Ciencia); she finished fifth.

The paucity of filly Derby entrants probably has something to do with the fact that, in 1946, the Oaks moved to its current position on Churchill’s racing calendar, the Friday before the Kentucky Derby, so no longer could contenders attempted both races. With a huge disparity in purses between these two races (in 1946, the $100,000 Derby dwarfed the mere $10,000 Oaks), it appears odd that more fillies didn’t attempt the Derby or other classics.

That’s not to say that there weren’t any talented fillies that continued to challenge the colts. Vagrancy finished second to Derby runner-up (and Preakness winner) Alsab in the 1942 Lawrence Realization, while Twilight Tear defeated the great handicap horse Devil Diver in the 1944 Pimlico Special. In 1945, the celebrated daughter of War Admiral, Busher finished second in the Santa Anita Derby, but won both the Hollywood Derby and Washington Park Handicap, in the latter defeating the great older horse Armed. Bed O’Roses won the 1950 Lawrence Realization and finished second in the Travers. The only subsequent filly place-getter in the Travers was Chris Evert, who finished third in 1974.

The Derby-winning success of Genuine Risk and Winning Colors has brought only a minor upspring in the number of fillies contesting major open-company races. Acorn winner Cupecoy’s Joy finished tenth in the 1982 Kentucky Derby, while in 1984 Mother Goose winner Life’s Magic ran eighth, finishing ahead of filly Arkansas Derby winner and post-time favorite Althea, who ran nineteenth. In 1995, Serena’s Song entered the Derby off an open-company victory in the Grade 2 Jim Beam Stakes, but finished sixteenth as stablemate Thunder Gulch won. Later that summer she was the first filly winner of the Grade 1 Haskell Invitational.

My Flag, daughter of Belmont Stakes winner Easy Goer and undefeated champion Personal Ensign (who herself won the Grade 1 Whitney Handicap as a 4-year-old over males, including Gulch), finished third in the 1996 Belmont Stakes. Santa Anita Oaks winner Excellent Meeting finished fifth in the 1999 Derby, but was eased in the Preakness.

With the success of these fillies, plus Rags to Riches, Eight Belles and Rachel Alexandra, more connections may be willing to challenge major open-company races, but only if the conservative attitudes of some owners and trainers is overcome. It took Jess Jackson purchasing Rachel Alexandra off her dominating Oaks win in 2009 to see her run in-and win-the Preakness, Haskell and Woodward last year. Who’s to say that if she had been geared towards a Triple Crown campaign all along, we wouldn’t today be enjoying our twelfth Triple Crown champion and first since 1978?

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