A Michigan native, before his successful time riding in the New York City area, Jimmy Butwell began his career at small race tracks in Nebraska and Colorado. Butwell rode for several prominent owners and in 1912, a year he led all North American riders in earnings, he rode Monocacy to victory for Harry Payne Whitney in the Victoria Stakes at Woodbine Racetrack in Toronto, Canada. Of his four mounts in the Kentucky Derby, Butwell's best finish was third in 1915. He won the 1913 Preakness Stakes and captured the Belmont Stakes in 1910 and again in 1917. In 1920 Butwell had more race wins than any jockey in the United States and the following year rode Herendesy to victory in Canada's most prestigious race, the Queen's Plate.