greatest American jockey of the second half of the 20th century.

Weighing only 1 pound 13 ounces (0.8 kg) at birth, Shoemaker grew to an adult weight of 98 pounds (44.5 kg) and a height of 4 feet 11.5 inches (1.51 metres). He moved with his family at age 10 to California, which became and remained his racing base. He started to ride at age six and began his track career in 1949.

Shoemaker rode the Kentucky Derby 24 times and won four: 1955, 1959, 1965, and 1986, achieving the last victory at age 54, which made him the oldest jockey to win that event. He won the Belmont Stakes five times—1957, 1959, 1962, 1967, and 1975—and the Preakness (Preakness Stakes) twice—1963 and 1967. He was the leading rider among North American jockeys in 1950, 1953, 1954, 1958, and 1959 and led in purses won in a single year 10 times. From 1957 on he earned more than $2 million annually. By the time he finally retired in 1989, horses he rode had won more than $120 million. After retirement from riding, he worked as a trainer, even after an automobile accident in 1991 left him a quadriplegic. Shoemaker rode more than 8,800 winners in his 41-year career. In 1981 he rode John Henry, winner of the Arlington Million, the first million-dollar stake race for Thoroughbreds. Other notable horses he rode included Gallant Man, Damascus, Spectacular Bid, and Swaps. The Shoe: Willie Shoemaker's Illustrated Book of Racing, written with Dan Smith, was published in 1976.