The (almost) fabulous fillies of the Preakness

Genuine Risk
Genuine Risk in a workout. Photo by NYRA.

From Kentucky to Maryland to New York, the three classic stakes that make up the American Triple Crown can define a horse’s reputation long after their time on the racetrack. For fillies especially, winning one of these races puts them in rarefied company, alongside Hall of Famers like Regret and Rachel Alexandra. Of the three races, it is the Mid-Atlantic’s own Preakness Stakes that boasts the highest number of filly victors, from Flocarline in 1903 to Swiss Skydiver in 2020.

In addition to those six distaff winners, the race has seen its share of great fillies compete in the middle jewel, including the daughter of one of those six and two Kentucky Derby winners who tried to make history twice. Meet four fabulous fillies who followed up their Run for the Roses with a turn in Maryland’s own classic.

Careful – 1921

Walter Salmon had made his fortune in real estate and then parlayed some of that fortune into owning racehorses, purchasing the filly Careful from Arthur B. Hancock’s Claiborne Farm. She won twelve of her seventeen starts at age two, including the Pimlico Nursery, the Schuylerville, and the Eastern Shore. Careful was retroactively named Champion Two-Year-Old Filly of 1920, sharing those honors with Harry Payne Whitney’s Prudery.

At three, both Careful and another filly, Prudery, were part of the 1921 Kentucky Derby field, facing the likes of the latter’s stablemate Tryster and the E.R. Bradley duo of Black Servant and Behave Yourself. That duo would finish one-two, with Behave Yourself outdueling his stablemate in the stretch to win by a head.

Salmon and trainer Eugene Wayland then took their filly to Baltimore to try the Preakness, where she met Tryster again and then his stablemate Broomspun. Careful was part of the early pace, even holding the lead briefly, before fading to twelfth.

The next year, Salmon’s filly was among the leading older distaffers of the year, winning four races including the Fall Highweight Handicap, where she defeated a field that included the 1922 Kentucky Derby winner Morvich.

Nellie Flag – 1935

The list of Preakness-winning fillies includes Nellie Morse, who took the 1924 edition just four days after her victory in the Pimlico Oaks, the race we now know as the Black-Eyed Susan. Seven years later, owner Bud Fisher, the cartoonist who had created the Mutt and Jeff strip, sent the mare to auction, where Warren Wright purchased her for $6,100. Thus, Nellie Morse became one of Calumet Farm’s first mares, as Wright converted his father’s Standardbred farm into one of the 20th century’s most formidable breeding and racing stables, its “devil’s red and blue” silks a staple of big-race winner’s circles.

Nellie Morse’s 1931 cover by American Flag, a son of Man o’ War, produced Nellie Flag, one of Calumet’s earliest stakes winners. At two, she won the Selima and Matron Stakes within her division and then faced colts in the Kentucky Jockey Club Stakes and brought home that prize as well.

The following year, 1935, she was one of the favorites for the Kentucky Derby, giving future Hall of Fame jockey Eddie Arcaro his first try at the Run for the Roses. She finished fourth behind Omaha, who went on to Baltimore to back up his Derby victory with a try at the Preakness.

Nellie Flag returned to face the Belair colt at Pimlico a week later, the lone filly in a field of eight. She sat midpack early, with Omaha behind her in sixth, but was not able to gain ground on the field as the Kentucky Derby winner went to the outside and took over the lead at the one-mile mark. The Calumet filly finished seventh and would later go on to become a prolific broodmare for Wright, producing ten foals including Nellie L., the 1943 Kentucky Oaks winner.

Genuine Risk – 1980

Sixty-five years after Regret became the first filly to win the Kentucky Derby, Genuine Risk stalked the pace and came on in the stretch at Churchill Downs to become the second filly to wear roses. A daughter of Exclusive Native, who had also sired Triple Crown winner Affirmed, Genuine Risk came to Baltimore the favorite to take the 1980 Preakness Stakes, poised to become the first filly to win more than one of the Triple Crown classics. In the field was a new shooter from the West Coast, a colt named Codex who happened to be trained by D. Wayne Lukas.

Riding Codex in the Preakness was Angel Cordero, Jr., a jockey with a reputation for being a fierce competitor. When Codex took the lead on the far turn, Genuine Risk started to move as well. Cordero looked over his shoulder to see the filly making her bid and moved Codex wider, herding the filly out as they entered the stretch. Jockey Jacinto Vasquez checked Genuine Risk, losing valuable momentum, as Codex took wing and began to pull away. The margin of victory was 4¾ lengths, the filly holding on for second.

After the race, Vasquez lodged a claim of foul against Cordero, the Pimlico stewards reviewing the film and determining there was no foul. An appeal to the state Racing Commission also was turned away, as pictures taken by a Baltimore Sun photographer revealed there was no contact between the horses.

To this day, the 1980 Preakness remains a point of controversy with many still believing Genuine Risk was robbed.

The filly would try the Belmont Stakes next, as would Codex. Over a muddy track, Genuine Risk tracked the front-runners until the stretch, briefly taking the lead until longshot Temperance Hill passed her inside the last furlong to win by two lengths. The filly rounded out 1980 with a win in the Ruffian Handicap and then won the Eclipse Award for Champion Three-Year-Old Filly on the strength of her performances throughout that Triple Crown season.

Winning Colors – 1988

Winning Colors is familiar to most racing fans as the third and most recent filly to win the Kentucky Derby, and like Genuine Risk, she went on to compete in the rest of the Triple Crown races, as well. Two weeks after her front-running Derby victory, she was at Pimlico to face Forty Niner and Risen Star, who had finished second and third in the Derby, and other also-rans from Louisville, including Private Terms, owned by Marylander Stuart Janney II.

In the Preakness, Forty Niner went straight to the lead, the filly going with him through fast early fractions of :23 for the first quarter and :47 for the half-mile. On the far turn, Risen Star ducked inside of the two front runners, taking the lead as they entered the stretch. Winning Colors did her best to hold onto second, ducking inside Risen Star in the final furlong, but that early pace had taken its toll on her. Brian’s Time passed her in the final strides, the filly holding on to finish third.

Winning Colors would go on to the Belmont, where she finished sixth behind Risen Star, and then would finish second behind the undefeated Personal Ensign in the Maskette and the Breeders’ Cup Distaff.

Secret Oath’s expected to run in the May 21 Preakness, where she could become the seventh filly – and seventh D. Wayne Lukas trainee – to capture the Middle Jewel. She would also be the third in the last 15 years – after Rachel Alexandra (2009) and Swiss Skydiver – to wear the Black-Eyed Susans.

But win or lose, Secret Oath will be joining a list of great and near-great distaff runners who have left their marks on the Preakness.



Bowen, Edward L., Legacies of the Turf, Volume 1. Lexington, KY: Eclipse Press, 2003. 136.

“Churchill Downs Past Performances.” Daily Racing Form. May 7, 1921.

“Churchill Downs Form Chart.” Daily Racing Form. May 8, 1921.

“Pimlico Form Chart.” Daily Racing Form. May 17, 1921. Macbeth, W.J. “Careful Races to Brilliant Victory in Fall HighWeight Handicap at Belmont Park Track.” New York Tribune. September 5, 1922.

Nellie Flag

Bowen, Edward L., Matriarchs, Volume 2. Lexington, KY: Eclipse Press, 2008. 124-127.

“Churchill Downs Form Chart.” Daily Racing Form. May 6, 1935.

“Pimlico Form Chart.” Daily Racing Form. May 13, 1935.

Genuine Risk

Winning Colors

  • NYRA- Genuine Risk, Jacinto Vasquez up, Misty Gallore (D. MacBeth up), Ruffian Hdcp, Belmont, 09.27.1980
  • Keeneland Library General Collection- Nellie Flag, Eddie Arcaro up, trainer B.B. Williams, 1934 #2
  • NYRA- Genuine Risk workout
  • Keeneland Library Sutcliffe Collection- Careful, 1929