[1] In his first year of racing at age two, Douglas Dodson rode Thinking Cap to his most important win in the 1954 Pimlico Futurity.
[4] Racing at age four and five, Thinking Cap continued to show his strength as a distance runner.
[5][6] In his last year of racing, Thinking Cap won the 1957 Southampton Handicap at Belmont Park.
Ridden by Eldon Nelson, the race was contested on a sloppy track over a distance of a mile and one-half.
Smart, a 1959 chestnut colt whose dam was Enchanted Eve, inherited Thinking Cap's endurance with wins in such top level races at a mile and one-quarter or more such as the Manhattan, Gallant Fox, and Massachusetts Handicaps, the latter he won back-to-back in 1964 and 1965.