Born Woodford Cefis Stephens in Stanton, Kentucky, his younger brother William Ward Stephens also became a successful trainer. Woody Stephens first started in racing as a jockey at age 16 but within a few years switched to training horses. After working as an assistant for several years, in the late 1930s he started training on his own, taking on horses from various owners. Near the end of the 1950's he was hired by the wealthy Harry Guggenheim as head trainer for his Cain Hoy Stable. The moved proved very successful, with Stephens training several champions and winning a number of major stakes races including the Kentucky Oaks three times. He remained with the Guggenheim operation for ten years before returning to run his own stable again in 1966.
In a career that spanned seven decades, Woody Stephens trained eleven Eclipse Award winners and his horses won over a hundred Grade 1 stakes races. Among his most notable was Henryk de Kwiatkowski's colt Conquistador Cielo, the winner of the 1982 Eclipse Award for Horse of the Year. Although Stephens trained horses that won the Kentucky Oaks for fillies five times, plus the Kentucky Derby twice and the Preakness Stakes once, he is most remembered for winning an unprecedented five straight Belmont Stakes between 1982 and 1986.
Woody Stephens was elected to the National Museum of Racing and Hall of Fame in 1976. In 1983, he won the Eclipse Award as the top trainer in the United States. Although always seen as an ordinary guy in rumpled clothes, his earnings from racing plus investments in successful breeding stock made him a very wealthy man.
Woody Stephens died in 1998 in Miami Lakes, Florida from complications of chronic emphysema eight days shy of his 85th birthday.
U.S. Triple Crown race winners:
- 1983 : Caveat
- 1984 : Swale
- 1985 : Creme Fraiche
- 1986 : Danzig Connection
- Woody Stephens autobiography Guess I'm Lucky! My Life in Horseracing (1985) Doubleday ISBN 0-385-19568-0