- Road to the Kentucky Derby
- Racing & Wagering
Hall of Famer Jerry Bailey won the 1993 and 1996 Kentucky Derby and the 1993, 2001 and 2005 Kentucky Oaks. He won a record 15 Breeders' Cup races, including five Breeders' Cup Classics, three consecutive from 1993-95. He was the US Champion Jockey six times and was awarded the Ecplise Award for Outstanding Jockey seven times (95-97 and 2000-03); the first person to win it three years in a row. He was awarded the George Woolf Memorial Jockey Award in 1993. Other notable mounts include: Cigar, Skip Away, Saint Liam, Black TIe Affair, Fit to Fight, Hansel, Congaree, Victory Gallop and Medaglia d'Oro.