Jerry Bailey was born on Aug. 29, 1957 in Dallas, Texas. He began riding Quarter Horse at the age of 12 and was riding Thoroughbreds competitively at 17 in 1974. Bailey primarily rode the New York and Florida circuits.
Among his accomplishments were two wins each in the Kentucky Derby, Preakness Stakes, and Belmont Stakes. Other notable victories for Bailey include the Travers Stakes (3), Hopeful Stakes (a record 6), Whitney Handicap (a record 5), Kentucky Oaks (3), Dubai World Cup (a record 4), Jockey Club Gold Cup (3), Hollywood Gold Cup (5), Pacific Classic, Del Mar Futurity, Pimlico Special (3), Arlington Million (2), Jaipur Stakes (a record 6), and Bonnie Miss Stakes (a record 5).
Bailey won 216 Grade 1 races, 16 New York riding titles, and had purse earnings of more than $296 million, which ranks No. 2 all time behind only fellow Hall of Famer Pat Day.
Bailey also distinguished himself as the all-time leader in Breeders’ Cup wins with 15, including five Classic winners (Black Tie Affair, the 133-1 Arcangues, Concern, Cigar and Saint Liam). His Breeders’ Cup earnings totaled $22 million.
Other significant riding feats were winning the New York Handicap Triple Crown in 1984 with Fit To Fight, winning 16 consecutive races with Hall of Famer Cigar, and riding seven winners at Gulfstream Park on Florida Derby Day in 1995.
Among Bailey’s significant mounts were Hall of Famers Cigar and Skip Away, as well as Black Tie Affair, Sea Hero, Hansel, Real Quiet, Grindstone, Concern, Congaree, Victory Gallop, Medaglia d’Oro, Empire Maker, and Saint Liam.
As President of The Jockeys’ Guild, Bailey was instrumental in lobbying for protective vests to be worn by all riders. Bailey won seven Eclipse Awards (1995-1997 and 2000-2003) and became the first jockey to win the award three years in a row. He also received the George Woolf Memorial Jockey Award in 1992.
At the time of his retirement, Bailey ranked 15th in victories. Since his retirement, Bailey has been involved in racing in a number of capacities, most notably as a commentator for ESPN at major televised races.
Jerry Bailey was inducted into the National Museum of Racing’s Hall of Fame in 1995.
Jerry Bailey and Cigar, 1995 Breeders' Cup