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Trying to find a yardstick to evaluate the better racing fillies, especially prior to 1940, is not an easy task, although it involves an enjoyable historical tour through decades of racing.

Among the earlier stock in this period of time, Regret sticks out most notably. Not only as the winner of the Kentucky Derby and an icon for fillies until joined by Genuine Risk and Winning Colors, but as winner of the Hopeful, Gazelle, and close second in the Brooklyn Handicap, Regret proved herself in the toughest competition in race after race.

Princess Doreen was a rugged mare, racing five seasons, and her toughness allowed her to become the leading money winner for mares. Among her most famous successes are the Kentucky Oaks, CCA Oaks, and handfuls of stakes or handicaps against colts.

The difficulty in evaluating these mares is that they largely had to race against colts all the time. Unless going in one of the major stakes set aside for fillies, it was tough to be a filly.

So the accomplishments of such as Nellie Morse, winner of the Preakness, and Chacolet, winner of the Dixie Handicap, Kentucky Special, and Latonia Cup, stand out brighter despite overall records that show plenty of losses along the way.

But for the fillies who could take the competition, it is interesting to see how many won important races that today would be considered exceptional results. The filly Nimba (by War Cloud) won the CCA Oaks and Alabama against fillies but thumped the colts in the Lawrence Realization in 1927 and the Metropolitan Handicap in 1928.

One of the most successful in this regard was Black Helen (1932 by Black Toney x La Troienne), who won the 1935 Florida Derby, American Derby, and Maryland Handicap but was fourth against Omaha in the Arlington Classic.

Black Maria, another daughter of Black Toney, won the Kentucky Oaks in 1926 and was a highly ranked filly season after season. Like Princess Doreen, who had only three foals, Black Maria did not have an extensive career as a broodmare, with only one foal.

But successful and extensive racing careers did not prevent mares from becoming successful producers. Among the best of these top early-century racers as broodmares was Alcibiades (winner of the Kentucky Oaks and dam of the standout racer Menow) and Escutcheon (winner of the Alabama and dam of Kentucky Oaks winner Mars Shield).

One of the most important mares of this half-century was Top Flight, unbeaten at 2 and never beaten by fillies. The daughter of Dis Donc was unbeaten in all her starts as a juvenile, including the Futurity at Belmont and the Pimlico Futurity. Big, progressive, and fast, Top Flight did not train on to defeat the colts at 3 but was still untouchable among fillies, with victories in the Acorn, CCA Oaks, Arlington Oaks, Alabama, and Ladies Handicap.

For speed and finesse, fillies had plenty to offer, and among the best were Mata Hari and Myrtlewood, both exceptionally fast and successful on the racetrack, and later they became important producers, as well.

And it is interesting that some of the better fillies and mares exploited talents at the more extreme parts of the racing spectrum — either sprinting or staying events — rather than the classics. Among these would be Dorimar, winner of the Saratoga Cup, and Vagrancy, winner of the CCA Oaks and 10 other races at 3, when she ran second to Alsab in the Lawrence Realization at a mile and three-quarters.

But the superstars of the “new age” of breeding and racing that dawned through the 1930s and then bloomed in the 1940s and ’50s were the classic performers.

Even the best of this period did not win a Triple Crown race, but two were so overwhelming that they were elected Horse of the Year in official polls.

These were War Admiral’s daughter Busher and Bull Lea’s daughter Twilight Tear. Both were good-class 2yos who improved at 3 to excel all competition.

Twilight Tear was the leader in 1944, when she defeated Kentucky Derby and Preakness winner Pensive in the Arlington Classic and older horses in the Pimlico Special.

The following season, Busher did much the same thing, dominating the classic colts, older horses, and her contemporary (and later champion) filly Gallorette.

These three formed the nucleus of the big five fillies of the 1940s, which also included champion Bewitch (the only horse to defeat Citation at 2) and Two Lea. The latter pair and Twilight Tear are all daughters of Bull Lea.

The 1950s were not a decade filled with the strength or depth of the preceding years, but those seasons of racing included some outstanding performers such as Real Delight (yet another star daughter of Bull Lea), Misty Morn (a daughter of Princequillo who could handle colts at longer distances), and the outstanding daughter of Royal Charger, Idun, a champion at 2 and 3.

The top 20 rankings*, as I see them:

Twilight Tear, Busher, Regret, Top Flight, Myrtlewood,

Real Delight, Two Lea, Black Helen, Idun, Gallorette

Alcibiades, Mata Hari, Misty Morn, Bewitch, Nellie Morse

Nimba, Black Maria, Princess Doreen, Chacolet, Escutcheon

*The mares are listed in order from one to 20. I did not see the point in making a list you couldn’t view without scrolling.