It helps that Bailey is sought after to ride for the sport's most successful trainers and that he was lucky enough to remain injury-free for another year. But, as Bailey has said, "The harder you work, the luckier you get."
It's safe to say that Hall of Fame jockey Jerry Bailey had a good year in 2001. Not only did he win 44 graded stakes races, 14 of which were grade I, he also ended the year as North America's leading rider by earnings and won his fifth Eclipse Award as outstanding jockey.At the end of a 2001 campaign that crisscrossed North America, and included visits to both Japan and Dubai, Bailey had absolutely shattered Gary Stevens' three-year-old record for earnings. His $22,597,720 bested the old mark by more than $3 million. Bailey's attack began soon after New Year's and stretched into the Christmas season. He won his first stakes race of 2001 on Jan. 11 at Gulfstream Park, and he ended the year with wins in the Hollywood Futurity (gr. I) aboard Siphonic and in the Bayakoa Handicap (gr. II) aboard Starrer, both Dec. 15 at Hollywood Park. In between was a victory in racing's richest race, the $6-million Dubai World Cup (UAE-I), which he won aboard Captain Steve. Bailey also managed to snag his 5,000th career win when he guided Gaviola to a victory in the Beaugay Handicap (gr. IIIT) over the Aqueduct turf on May 6. Bailey's win aboard Squirtle Squirt in the Penske Auto Center Breeders' Cup Sprint (gr. I) gave him an even dozen victories in Breeders' Cup competition to place him in a tie with fellow Hall of Fame jockey Pat Day.