Hall of Fame trainer LeRoy Jolley, who twice won the Kentucky Derby and played a role in one of the most famous match races in Thoroughbred history, died Monday at Albany Medical Center in Albany, N.Y., from lung cancer. He was 80. Born in Hot Springs, Ark., Jolley was in racing virtually his entire life. He grew up mostly in Florida as the son of highly successful trainer Moody Jolley. “All I ever wanted to do was train horses,” Jolley said in an Aug. 1975 article in People magazine. He won his first race as a trainer at age 20 and eventually went to work for some of the most prized clients in America. In 1962, at age 24, Jolley saddled the 11-10 favorite for the Kentucky Derby, Ridan, who finished third. In 1975, Jolley won his first Derby, with Foolish Pleasure. Owned by John L. Greer, Foolish Pleasure would face the great filly Ruffian two months later in a widely anticipated match race at Belmont Park. Ruffian broke down early in the race and was ultimately euthanized, much to the horror of those watching in person and on television. In 1980, Jolley won his second Derby, with Genuine Risk, who was owned by Bert and Diana Firestone and became just the second of three fillies ever to win the race in its 143-year history. Both of his Derby winners are in the Hall of Fame. Jolley was inducted into the Hall of Fame in 1987 after winning numerous other major stakes, including the 1979 Travers at Saratoga with General Assembly and the 1986 Breeders’ Cup Turf with Manila. Meadow Star, the 1990 BC Juvenile Fillies winner, was his last superstar. His other top horses included Honest Pleasure, second as the 2-5 favorite in the 1976 Kentucky Derby; What a Summer, the champion sprinter of 1977; and Gulch, a top 3-year-old of 1987. In recent years, Jolley maintained a small stable while mostly splitting time between the horse-centric towns of Saratoga Springs, N.Y., and Ocala, Fla. His numbers had steadily fallen from his peak season of 1986, when his horses won 58 races and nearly $4.3 million. From 2006 until his death, he won just 11 races from 219 starts, with his last winner coming in December 2015 in a maiden-claiming race at Tampa Bay Downs. In a Daily Racing Form interview in February at Gulfstream Park in Florida, Jolley seemed wistful about not getting the opportunities he once did to train top horses. “They’re hard to come by,” he said. “I’m always looking. But yeah, they’re tough to find.” At his career peak, however, Jolley was widely known as a consummate horseman with a passion for winning. After learning under his father while stabled alongside the likes of Sunny Jim Fitzsimmons and other long-gone icons, Jolley was respected throughout the industry for his intelligence, quick wit, and his many years of dedication to the Thoroughbred and the sport of racing. “He was a very good friend and an excellent horseman,” said D. Wayne Lukas, a fellow Hall of Fame trainer. “He was very much overlooked in his later years, but you don’t win a couple Derbies unless know what you’re doing.” Lukas assumed the training of Gulch from Jolley and won the 1988 BC Sprint with him. Lukas said the switch never affected their friendship. “I always thought he was so classy about that,” said Lukas. “It never fazed him. I’d do an interview on Gulch and he’d come up later and kid me, ‘Hey, you failed to mention me.’ He was always a black-and-white guy where you knew where you stood with him.” Jolley is survived by his two adult sons, LeRoy Jr. and Tim, and a daughter, Laurie.