His father died when he was 3, and two years later his mother married Trainer Carey Winfrey Bill Winfrey was born Colin Dickard. His father died when he was 3, and two years later his mother married Hall of Fame trainer, G. Carey Winfrey. He was officially adopted and took Winfrey's last name. At age fifteen he became a jockey, but weight gain forced him to turn to training. In 1932 he became the youngest licensed trainer in the United States. His career was interrupted by service with the United States Marine Corps during World War II. He retired after the 1969 season but returned to training for two more years in 1977 and 1978. During his career, Bill Winfrey trained thirty-eight stakes winners including seven champions of which three were inducted in the U. S. Racing Hall of Fame. The most noted of them was two-time American Horse of the Year, Native Dancer. Winfrey was inducted into the United States' National Museum of Racing and Hall of Fame in 1971. A resident of San Clemente, California, he died at age seventy-seven of complications from Alzheimer's disease.