1999: Laffit Pincay, Jr. Becomes the World's Winningest Rider

In the waning days of 1999, the sport of Thoroughbred racing was on watch. An event was coming, and the question was not "if." The question was "when."

For Laffit Pincay, Jr., who was at the center of it all, it was the culmination of a thirty-five year career that began in his native Panama. He was a teenager in those days, his whole life and career yet to play out. As the millenium reached its conclusion, the Hall of Famer and living legend was about to experience the crowning achievement of his time as a jockey.

In the thirty-five years since he won his first race at Presidente Remon racetrack in Panama, Pincay had grown into one of the leading riders in history. He won scores of riding titles, led the nation in wins and earnings multiple times, and