Woody Stephens started in racing as a jockey at age 16 but within a few years switched to training horses.

Near the end of the 1950s, he was hired by the wealthy Harry Guggenheim as head trainer for his Cain Hoy Stable.

The move proved very successful, with Stephens training several champions and winning a number of major stakes races, including the Kentucky Oaks three times.

In a career that spanned seven decades, Stephens trained eleven Eclipse Award winners, and his horses won over a hundred Grade 1 stakes races.

Although he often wore rumpled clothes, his earnings from racing plus investments in successful breeding stock made him a very wealthy man.