[1] Born in Hoboken, New Jersey, Raymond Workman's mother was a native of Washington, D.C., and after her husband's death she and the children returned to live there.
His abilities quickly reached a level that in just his second year of racing he signed a contract to go to New York City to ride for one of the country's preeminent owners, Harry Payne Whitney.
On January 21, 1930, he was married to Marion Elizabeth Burch of Washington, D.C.[4] During his career, Sonny Workman competed in four Kentucky Derbys with his best result two fourth-place finishes.
Not entered in that year's Kentucky Derby, Harry Whitney's colt, Victorian with Sonny Workman aboard, won the May 11, 1928, Preakness Stakes at Pimlico Race Course.
However, for years he had battled weight gain [6] and his exceptional riding skills were increasingly being hampered by the need for constant dieting.