In 1916 Pickens won two of the three races that would later be part of the Canadian Triple Crown series.

His wins came aboard distiller Joseph Seagram's colt Mandarin in the 1916 Breeders' Stakes and in Canada's most prestigious[citation needed] race, the King's Plate.

[1] That year he also won the Coronation Futurity Stakes for the Seagram Stable.

Among his other accomplishments in racing, on May 28, 1918, he rode four winners at Prospect Park Fair Grounds on Coney Island, New York.

[2] In winters he rode at Oriental Park Racetrack in Havana, Cuba, where in 1924 he was one of the track's top jockeys.