Billy The Shoe's Last Ride: A Derby Upset at 54

In 1986, the Kentucky Derby saw a legendary upset when jockey Billy Shoemaker, at 54 years old, won his fourth and final Derby on the 17-1 longshot Ferdinand. This victory, 40 years ago from the current date, is still celebrated in racing history.

Shoemaker, who had already amassed 8,833 wins and was a well-respected figure, faced significant challenges. He started from the notoriously difficult No. 1 post position and trailed the entire field for much of the race. However, Shoemaker executed a brilliant maneuver on the final stretch, guiding Ferdinand from the back to a surprising win.

The win was also significant for trainer Charlie Whittingham, who secured his first Kentucky Derby victory at age 73. Shoemaker's career concluded with this memorable Derby win and a subsequent Breeders' Cup Classic victory in 1987. His legacy includes 8,833 wins, placing him third in North American racing history.

Later, Shoemaker's life took a difficult turn when he was paralyzed in a car crash in 1991, a consequence of driving while intoxicated. He continued as a trainer from his wheelchair until his passing in October 2013. Ferdinand, the 1986 Derby winner, was eventually sent to stud in Japan, and reports surfaced in 2002 that he might have been sent to a slaughterhouse, sparking outrage and calls for legislative action.

The era of 1986 was notable for legendary sports moments, including Jack Nicklaus winning the Masters at 46, a time often characterized by celebrating sports history and iconic figures.