As a 5-year-old in 1993, Fly So Free captured the Fall Highweight Handicap (gr. II) carrying 135 pounds. He was retired with a dozen wins from 33 starts and earnings of $2,330,954 and entered stud at Three Chimneys near Midway, Ky.Fly So Free raced in the colors of Broadway musical producer Tommy Valando and is still owned entirely by his widow, Elizabeth Jones Valando.
Robert N. Clay of Three Chimneys Farm announced today that Eclipse Award winner Fly So Free is being pensioned because of health concerns. "Fly So Free has developed a heart condition that could be aggravated by continued breeding activity," Clay said. "We have chosen to retire him because we feel it is in the horse's best interest. He will remain, of course, at Three Chimneys."Fourteen-year-old Fly So Free (Time for a Change--Free to Fly, by Stevward) is the sire of nine stakes winners, including Captain Steve, the fifth-leading North American-based earner of all time, with earnings of $6,828,356. Captain Steve won the Dubai World Cup (UAE-I), Swaps Stakes (gr. I), Donn Handicap (gr. I), and Hollywood Futurity (gr. I), plus several other graded races. Fly So Free also sired Canadian champion Free Vacation and 2002 added-money winner Take the Cake. Fly So Free was champion 2-year-old male after winning the 1990 Breeders' Cup Juvenile (gr. I) and Champagne Stakes (gr. I). At three, he won the Hutcheson Stakes (gr. II), Fountain of Youth Stakes (gr. II), and Florida Derby-G1 to sweep the major Florida prep races for the Kentucky Derby (gr. I). He then ran second in the Blue Grass Stakes (gr. II) and fifth in the Run for the Roses. Later that year, he won the Jim Dandy (gr. II) and Riva Ridge (gr. III) Stakes.