Racing Hall of Fame inductee Damascus, he was owned by New York City Broadway theatre producer and music publishing company owner Tommy Valando and his wife Elizabeth.
In 1990, Fly So Free capped off a successful two-year-old racing campaign with a win in the Breeders' Cup Juvenile.
A few weeks later, in mid-April's Blue Grass Stakes, Fly So Free finished second to Strike the Gold.
Racing at age four, Fly So Free met with modest success, most notably a second to Strike the Gold in the 1992 Pimlico Special.
After a 9th-place finish in that year's Breeders' Cup Sprint, Fly So Free was retired to stud duty at Three Chimneys Farm in Midway, Kentucky, where he remained for the rest of his life.