A United Press International news release at the time of his death called him "one of the most promising young jockeys in the country.
"[2] Born in London, Kentucky, Roy Gilbert was one of 19 children.
[2][3] He began working in the Thoroughbred racing industry in 1954 as a stable hand then as an exercise rider for the future U.S.
In 1957, Gilbert began riding professionally but in June 1958 was sidelined for a time after he suffered a broken leg as a result of being thrown from his horse during a race at Monmouth Park Racetrack in Oceanport, New Jersey.
On April 4, 1961, at Aqueduct Racetrack in Queens, New York, Gilbert was thrown from his horse Plenty Papaya, during the fourth race, and struck his head on the concrete base of a rail post.