Jerry D. Bailey is a retired American Hall of Fame jockey. He began his racing career in November 1974. His first mount was on a horse named Pegged Rate, who ran off the board. He notched his first career win the next day on his second career mount, Fetch, at New Mexico's Sunland Park, and has gone on to win 5,892 races. Among his numerous wins, he can boast the New York Handicap Triple in 1984, six victories in American Classic Races races, and a record 15 wins in Breeders' Cup races, including five Breeders' Cup Classics. Three of his Breeders' Cup Classic wins were consecutive. Bailey is perhaps most famous among racing fans as the regular rider of 1990s great Cigar.
In his 2005 book titled Against The Odds, Bailey wrote about his battles with alcoholism that affected a large part of his early career.
When the 2003 Thoroughbred racing Eclipse Awards were handed out on January 26, 2004, Jerry Bailey was proclaimed the outstanding jockey in North America for an unprecedented seventh time; in 1997 he had been the first jockey to win three consecutive Eclipse Awards.
In 1992, Bailey was selected for the George Woolf Memorial Jockey Award, arguably the top lifetime achievement award for North American jockeys. In 1993, he was voted the Mike Venezia Memorial Award for "extraordinary sportsmanship and citizenship". He was inducted into the National Museum of Racing and Hall of Fame in 1995.