Fly So Free was an American Thoroughbred Champion racehorse. A grandson of U.S. Racing Hall of Fame inductee Damascus, Fly So Free 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. Voted 1990's U.S. Champion 2-Yr-Old Colt, he went into the 1991 racing season ranked as a top contender for the U.S. Triple Crown series of races. En route, Fly So Free won the spring of 1991's Hutcheson Stakes the Fountain of Youth Stakes and then the Florida Derby in which he defeated two other top three-year-olds, Strike the Gold and Hansel. A few weeks later, in mid-April's Blue Grass Stakes, Fly So Free finished second to Strike the Gold.
For the 1991 Kentucky Derby, bettors made Fly So Free the second choice to Hansel but both horses disappointed, Fly So Free finishing fifth and Hansel tenth to winner Strike the Gold. Fly So Free was not entered in the Preakness Stakes or the Belmont Stakes, but went on to win the Riva Ridge and Jim Dandy Stakes.
Racing at age four, Fly So Free met with only modest success, most notably a second place finish to Strike the Gold in the 1992 Pimlico Special. At age five, near the end of the 1993 racing season he won the Fall Highweight Handicap at Aqueduct Racetrack, a race in which a horse's ability to carry weight is put to the test. After a 9th-place finish in that yearâ€™s Breeders' Cup Sprint, Fly So Free was retired to stud duty at Three Chimneys Farm in Midway, Kentucky where he would remain for the rest of his life.