As we were poignantly reminded this week, only three fillies have won the Kentucky Derby in its 145-year history. Genuine Reward, one of only two foals produced by 1980 Derby winner Genuine Risk, died last week at Old Friends Retirement Home for Thoroughbreds near Lexington, Ky., after being saved from slaughter three years ago by Seabiscuit author Laura Hillenbrand and Old Friends’s Michael Blowen. Sadly, both of Genuine Risk’s foals were colts, so she has no tail-female descendants. Regret, the first female Derby winner of 1915, by contrast, enjoyed a long and productive life as a broodmare, producing 11 foals, including stakes winner Revenge, by Chicle. Regret’s family thrived for many years, and her descendants include First Fiddle, Saratoga Handicap winner Divine Comedy, and Gazelle winner Avenger. Regret’s female line produced a high-class runner as recently as 2016, when her ninth-generation tail-female descendent Lucy N Ethel, by During, who is still in training, won the Grade 2 Prioress and Grade 3 Old Hat. Thankfully, the broodmare career of the third Kentucky Derby-winning filly, Winning Colors, by Caro, is more like Regret’s than that of Genuine Risk. Her granddaughter Eskimo Kisses, by To Honor and Serve, won Saturday’s Grade 1 Alabama Stakes, and is the fourth stakes winner and first Grade 1 winner among her descendants. :: DRF BREEDING LIVE: Real-time coverage of breeding and sales Bred in Kentucky by Don and Shirley Sucher’s Echo Valley Horse Farm, Winning Colors was purchased for $575,000 by trainer D. Wayne Lukas on behalf of Eugene V. Klein at the 1986 Keeneland July sale. She won both her starts at 2 but was beaten a neck by the more experienced top-class filly Goodbye Halo in her first stakes attempt at 3 in the Las Virgenes. She bounced back from that with a tour-de-force right-length trouncing of Jeanne Jones and Goodbye Halo in the Grade 1 Santa Anita Oaks, and then proved she was the best 3-year-old of any gender on the West Coast, administering a 7 ½-length defeat to Grade 1 winner Lively One in the Grade 1 Santa Anita Derby. Winning Colors was a massive filly, as powerful as most colts, and Lukas had no qualms running her against the best Eastern colts in the Kentucky Derby. She led all the way again, holding off champion 2-year-old Forty Niner’s closing bid by a neck, with the somewhat unlucky Risen Star three lengths away in third. Winning Colors had been allowed to race freely on the lead in the Derby, but in the Preakness, jockey Pat Day hustled Forty Niner to the lead and kept Winning Colors out in the middle of the track all the way around the turn and down the backstretch. That allowed Risen Star to race through the gaping hole on the rail heading into the far turn, and he drew away to win from the late closing Brian’s Time, with Winning Colors hanging on for third. Well beaten in the Belmont, she returned that fall to run second to the undefeated Personal Ensign in both the Grade 1 Maskette and the Breeders’ Cup Distaff. That assured her of champion 3-year-old filly honors, but she was not quite the same horse at 4, winning only one minor stakes. Sold for $4.1 million to Gainesway Farm at Klein’s dispersal sale in 1989, she produced 10 foals, six of which won, including the stakes-placed fillies Golden Colors, by Mr. Prospector, dam of Japanese stakes winner Cheerful Smile, by Sunday Silence, and Ocean Colors, by Orientate. Bred in Kentucky by Gainesway Thoroughbreds, Eskimo Kisses is the fourth foal of Winning Colors’s unplaced daughter Silver Colors, by Mr. Greeley. Silver Colors's Candy Ride gelding Silver Ride recently ran third in Saratoga’s Tale of the Cat Stakes. She has since produced an Empire Maker colt who is entered in the upcoming Keeneland September sale, and a weanling filly by Union Rags. Eskimo Kisses is the fifth stakes winner and first Grade 1 winner sired by the hitherto disappointing To Honor and Serve, by Bernardini. To Honor and Serve was exported to Korea earlier this year. To Honor and Serve, winner of the 2011 Grade 1 Cigar Mile and 2012 Grade 1 Woodward, is also sire of recent Grade 3 winner Mr. Freeze. Like Regret, Winning Colors is a member of one of the best families in the American Stud Book. Her stakes-placed half-sister All Dance, by Northern Dancer, is dam of Group 1 Japan Cup winner Tap Dance City, by Pleasant Tap. Winning Colors’s dam, stakes-placed All Rainbows, by Bold Hour, is half-sister to Racing Hall of Fame member Chris Evert, by Swoon’s Son; granddam of champion Chief’s Crown, by Danzig; and third dam of Grade 1 winners Sightseek, Tates Creek, and Etoile Montante. Winning Colors’s second dam is foundation mare Miss Carmie, by T.V. Lark.