 Whimsical was sired by Orlando, out of the mare, Kismet, who was sired by United States Racing Hall of Fame stallion, Hindoo.As a two-year-old Whimsical won the Belles Stakes and Golden Rod Stakes at Sheepshead Bay and finished second when racing against colts in the Champagne Stakes.At age three she won the Standard Stakes at Gravesend in which she defeated 1905 Preakness Stakes winner Cairngorm and 1905 Futurity Stakes winner Ormondale.