In 1961, the 24-year-old LeRoy Jolley was the trainer of the colt Ridan who at age two went undefeated in seven races including wins in the Arlington Futurity and the Washington Park Futurity. Owned by his family along with two other partners, at age three Ridan gave LeRoy Jolley victory in record time in the Hibiscus Stakes, plus the first of his three Blue Grass Stakes wins. He then earned the first of his two Florida Derbys while defeating the future Hall of Fame filly, Cicada. The heavy favorite going into the Kentucky Derby, Ridan ran wide throughout the race and wound up third in a hard fought race where he and Roman Line finished a neck behind upset winner Decidedly whom Ridan had easily beaten in the Blue Grass stakes. In that year's Travers Stakes at the Saratoga Race Course, Ridan lost by a fraction of a nose to Jaipur in one of the most dramatic races in American Thoroughbred racing history and one that is still written and talked about today.