 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 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.Fly So Free sired five Group/Graded stakes race winners, including the 1999 Canadian Female Turf Horse Champion Free Vacation and the 2001 Dubai World Cup winner, Captain Steve.