The oldest man to win the Kentucky Derby, Bill Shoemaker was also one of the smallest. Check out the life and times of America’s most famous jockey.
During his 41-year career, jockey Bill “the Shoe” Shoemaker won five Belmont Stakes, four Kentucky Derbys, and two Preakness Stakes. He rode in more than 40,000 races and won 8,833 of them, a record that stood until 1999 when Laffit Pincay Jr. broke it. In all, Shoemaker won more than $120 million in purses and had a reputation for being gifted with horses—his firm but gentle hand was just what the animals needed to be coaxed first over the finish line again and again.
Shoemaker was born in Texas in 1931. He weighed only 1 pound, 13 ounces, at birth and no one expected him to make it to the next morning. (One legend says that his grandmother put in him a box on the stove to keep him warm.) He survived, though, and grew into a healthy but small child. After his parents divorced, Shoemaker moved with his father to California, and it was there that he fell in love with horses.
As a teenager, Shoemaker got a job as a stable and exercise boy and then quickly moved up to jockey. He was a perfect size: under 100 pounds and just 4'11". His first professional race was in March 1949, and his first win came a month later. Of that race, Shoemaker said, “I almost went into shock. She was a chestnut filly, and you bet I remember her. I think I got about 10 dollars.”
Shoemaker’s first Kentucky Derby win came in 1955 on a chestnut stallion named Swaps. But it was his 1957 Derby loss that got most people talking. That year, Shoemaker mistook a furlong post for the finish and slowed his horse (Gallant Man) just a few feet too soon. He lost when Iron Liege raced up from behind and beat them by a nose. It was an embarrassment for sure, but also a mistake other jockeys understood. Said Eddie Arcaro, “After the race, they did what they should have done 50 years before. They put lines on the fence to show the finish.” And five weeks later, Shoemaker and Gallant Man won the Belmont by eight lengths.
Shoemaker won the Derby again in 1959 and 1965, but then seemed to slow down. He broke his leg in 1968 when a horse threw him, and a year later, he was injured again when a horse trampled him in the paddock. During the 1970s, Shoemaker seemed fated for retirement. But then, in 1986, along came a horse named Ferdinand.
Ferdinand was a long shot (17–1 odds at the 1986 Kentucky Derby), but Shoemaker thought they had a chance. Maybe it was his skill with horses that gave him that confidence. According to Jay Hovdey, one of Shoemaker’s friends,
There’s a lot for the horse to be worried about [during a race] . . . What Shoemaker did, he had an innate light touch, a very sensitive touch with his hands. The hands were on the reins, the reins were on the bit, and the bit was in the horse’s mouth. That’s the way Shoemaker communicated in a very gentle, very insinuating kind of command that the horse needed and responded to.
It worked. Ferdinand lagged behind out of the starting gate, but going into the backstretch, he started to advance. Shoemaker urged the horse on and, at the top of the stretch, found a hole. They navigated through traffic and took the lead . . . eventually winning by 2½ lengths. It was a victory that capped Shoemaker’s already remarkable career. He was 54, the oldest jockey to win the Derby. (Tragically, Ferdinand’s later life became a catalyst for the racehorse-rescue movement. For more on that story, turn to page 123.)
Shoemaker retired from racing in 1990 and began training horses. Ultimately, he trained 157 winners. He died in 2003, but his legacy as a racing hero was firmly established. He was also humble. Of his skills on the racetrack, Shoemaker once said, “I never felt I was gifted. I got the right horses at the right time, and that made me good.”