On May 3, 1986, 54-year-old Willie Shoemaker, aboard 18/1 shot Ferdinand, becomes the oldest jockey ever to win the Kentucky Derby. The victory was just one of Shoemaker’s 8,833 wins, a record that stood until 1999, when it was broken by Laffit Pincay.

William Lee Shoemaker was born prematurely on August 19, 1931, in the West Texas town of Fabens. He weighed just two pounds at birth, and doctors predicted he would not survive the night. Even as a full-grown man, “Shoe” was just 4 feet 11 inches tall and 98 pounds.

When he was 10, Shoemaker moved with his father to Los Angeles, where he won a Golden Gloves boxing championship in the 95-105 pound class. Seven years later, on March 19, 1949, he first rode a horse professionally; he was 17. Shoemaker won his first professional race a month later, and soon became known for his patience and great hands. He rarely used his whip and instead relied mostly on the bit and the harness. In 1953, Shoe set a record for most wins in one year with 485. His record in Triple Crown races was similarly outstanding: He won a total of four Kentucky Derbys, two Preakness Stakes and five Belmont Stakes. He placed or showed (second and third place, respectively) in another 14 Triple Crown races over the course of his career

Shoemaker’s most famous run, however, was one he did not win. In the 1957 Kentucky Derby, he mistook the 1-16 mile marker for the finish line and stood up in celebration. He and his horse, Gallant Man, ended up losing the race by a nose. Shoe responded with characteristic calm, explaining to fans and reporters that the course had been changed and that he’d been confused by the lack of a finish marker.

After recovering from a broken leg that forced him to miss a year of racing, Shoe broke the career record for wins on September 7, 1970, passing Johnny Longden with his 6,033rd victory. Shoe’s last win, on horse Beau Genius, came nearly 20 years later on January 20, 1990, at Gulfstream Park in Florida. It was his 8,833rd win in 40,350 races. He collected nearly $123 million in purses in his 40-year career.

In 1991, the year after Shoemaker retired from racing, a single car drunk-driving accident left him paralyzed from the neck down. Though he was unable to walk, he retained his sense for horses and returned to training them from his wheelchair.

Shoemaker died in his sleep on October 12, 2003, at his home in San Marino, California.