At age sixteen, he embarked on a career in Thoroughbred racing, breaking yearlings at William L. McKnight's Tartan Farms near Ocala, Florida.
For the next twenty-three years McCauley was a top jockey at tracks in the U.S. northeast and notably rode five winners from five mounts in a single racecard on November 18, 1985, at Meadowlands Racetrack in East Rutherford, New Jersey.
On July 10, 1998, Herb McCauley suffered compound fractures to the tibia and fibula of his left leg in an accident at Monmouth Park.
Having suffering from bulimia since his teens, in a May 1999 conference on the various disorders some athletes have to deal with, McCauley spoke publicly for the first time about his battle as a jockey to maintain riding weight that resulted in constant binging and purging.
Following an intense training program, in September 2007 he returned to riding competitively and a few weeks later earned his first win in nine years at Meadowlands Racetrack.