Leather racing saddle used by legendary Hall of Fame jockey Jerry Bailey in 1986. The name "Bailey" is written in white paint on the bottom of each stirrup. The notation "J.D Bailey 8/25/86" is written in white paint on the underside of the saddle. Interestingly, one can see a black-ink notation under the white paint which appears to read "Ussery 7/25/__", indicating that the saddle might have also been used by Hall of Fame jockey Bob Ussery as well. This saddle originates from the same collection as the Jerry Bailey full racing ensemble that appears in this auction. The saddle is well worn and displays several scuffs and abrasions. Jerry Bailey won 5,893 races during his illustrious career, including two wins each in the Kentucky Derby, Belmont Stakes, and Preakness. When he retired in 2006, he ranked second on the career North American money list with $296 million (currently ranks third). He was elected to the United States Racing Hall of Fame in 1995.