Kentucky Derby Lucky Losers: Cleopatra (1920)

Oct 29, 2025 Jennifer Kelly

Regret’s 1915 Kentucky Derby victory showed that fillies certainly could beat the boys in the Run for the Roses. In 1920, another distaffer challenged colts and geldings beneath the Twin Spires at Churchill Downs: Cleopatra, a stakes-winning filly from the barn of William Robinson Coe. Derby Day 1920 was not her day to shine, but this lucky loser started a lineage of challengers that aspired to make the Kentucky Derby their own.

A Queenly Contender

The upheaval of World War I saw many British horses coming west to the United States as breeders sought new bloodstock for the American market. In 1916, Arthur B. Hancock of Ellerslie in Virginia and Claiborne Farm in Kentucky was among those traveling across the Atlantic to buy mares like Gallice, a daughter of British stakes winner Gallinule, in foal to Middle Park Stakes winner Corcyra. The following spring, Gallice foaled a lovely chestnut filly with a splotch of white on her forehead, gracefully made with a pedigree that promised stamina.

Gallice’s filly would join other Claiborne and Ellerslie yearlings in Saratoga for the Fasig-Tipton sale and fetched $4,100 from trainer William H. Karrick, bidding on behalf of owner William Robertson Coe. The businessman named the chestnut filly Cleopatra and sent her to Karrick to prepare for the racetrack. She finished eighth in her debut, a five-furlong maiden race at Saratoga in early August 1919, and then got her first win in a 5 1/2-furlong maiden three days later.

She stepped up to stakes company in the Spinaway, but could do no better than ninth there. She then reeled off four consecutive second-place finishes, including one behind Man o’ War in the Hopeful, before winning her first stakes, the Champagne at Belmont Park. She finished her two-year-old season with two wins in her eleven starts, her performances against Man o’ War and others promising that 1920 would be a successful year for Coe’s filly.

An Iron Lady

When Samuel Riddle declined to send Man o’ War to Louisville for the Kentucky Derby, the 46th edition of the classic race attracted a stacked field of 17, including Upset, the lone horse to beat Big Red to the wire; the good gelding Paul Jones; and Cleopatra, the lone filly in the field. She prepared for her turn at Churchill Downs with the six-furlong Wicomico Purse at Pimlico. Cleopatra opened her three-year-old season with a third-place finish as the even-money favorite and then shipped west for the Kentucky Derby.

Coe’s filly was not a factor in the crowded field, ultimately finishing 15th behind Paul Jones and Upset, who dueled down the stretch, Paul Jones eking out the victory by a head. A week later, she was back at Pimlico for the Pimlico Oaks, now known as the Black-Eyed Susan Stakes, and easily defeated a field of four other fillies. After that win, Karrick sent her on a tough campaign, starting twelve more times at racetracks like Belmont Park, Latonia, and Saratoga. Cleopatra won five more times that year, beating the boys in the Huron Handicap and taking the Coaching Club American Oaks and the Alabama Stakes before finishing the year with a 14-furlong test in the Latonia Championship.

In a short field of five, which included Harry Payne Whitney’s John P. Grier, the colt who gave Man o’ War a stout challenge in that year’s Dwyer, she took over the lead a half mile in and kept the boys at bay the rest of the way, “scor[ing] in such a fashion as to leave no room for doubt as to her superiority, particularly over a long distance,” J.L. Dempsey wrote in the Daily Racing Form. Her time of 2:56 4/5 set a new track record and nearly equaled the American record for the 1 3/4-mile distance. Satisfied with his filly’s performance that season, Coe declared her retired to broodmare life, saying that “she had stood a campaign which only an iron horse could stand,” confident that his daughter of Corcyra would make an excellent mother.

Indeed, what this lucky loser did was start a line of horses who would also try to make the Kentucky Derby their own.

Rosy Connections

For Coe’s Shoshone Stud, Cleopatra produced eight foals, including Pompey, a colt by Sun Briar. An excellent two-year-old, Pompey would win the first Wood Memorial Stakes before finishing fifth behind Bubbling Over in the 1926 Kentucky Derby. He would then go on to sire Pompoon, who defeated War Admiral in the National Stallion Stakes at two before finishing second behind the eventual Triple Crown winner in the 1937 Kentucky Derby. Pompey also would sire the mare Delmarie, the dam of the 1951 Kentucky Derby winner Count Turf.

Today’s Triple Crown Winner Spotlight falls on War Admiral.

This pint-sized son of Man O’ War captured the Triple Crown in 1937, and while his list of accomplishments is plentiful, he is often remembered for losing a legendary match race against Seabiscuit in 1938. pic.twitter.com/wvICk2pHwY

— TwinSpires Racing 🏇 (@TwinSpires) August 27, 2020

Cleopatra may not have worn the roses herself, but she influenced a succession of generations that took their own shots at the Kentucky Derby and even won one long after the chestnut filly was gone. She stood up against a titan in Man o’ War and still made her own history on the racetrack, a testament to the fighting spirit of the Thoroughbred.