The phrase “born to greatness” can certainly be applied to 1995 Breeders’ Cup Juvenile Fillies winner My Flag. She was produced by the mating of two champions — Easy Goer and Personal Ensign. Her mother, Personal Ensign, won the 1988 Breeders’ Cup Distaff to end her career undefeated while narrowly defeating Kentucky Derby winner Winning Colors. Like her parents, My Flag was owned and bred by Ogden Phipps and trained by Shug McGaughey.
In the Juvenile Fillies, My Flag faced two major hurdles — a muddy surface at Belmont Park she never cared for and the presence of eventual 2-year-old filly champion Golden Attraction. My Flag lost to Golden Attraction in three graded stakes races leading up to the Breeders’ Cup. In the Juvenile Fillies, she emulated her mother and rallied from far back over the wet track to upset a champion. My Flag held her form well as a 3-year-old by winning three Grade 1 races.