He is 48, a Hall of Famer who has won seven Eclipse Awards as the nation's top jockey, won nearly every major race and remained at the top of the money list for riders. Jerry Bailey owns the Breeders' Cup, too.
He has more victories, 14, than any other jockey in the 21-year history of the event, and today he will ride horses in seven of the eight races, four of his mounts being morning-line favorites.
Whether or not he wins the Classic with Saint Liam (3-1), the Juvenile with First Samurai (8-5), the Turf with Shakespeare (3-1), or the Filly & Mare with Ouija Board (5-2), Bailey will return to his home in Florida for November and decide if he is ready to retire.
In the last couple of years, Bailey has always found a reason to come back to the racetrack. He has avoided serious injury; overcome alcoholism, which he chronicled in his autobiography, "Against the Odds: Riding for My Life"; and is considered something between a legend and an invaluable asset for those who employ him.
"I don't have any instructions for Jerry when he's on my horses," said Richard Dutrow Jr., who trains Saint Liam. "He's the best, period."
It is why the English-based trainer Edward Dunlop gave him the mount on Ouija Board, a filly owned by Lord Derby. And it is why Bailey is able to work the closest thing to banker's hours that a professional rider can.
He did not ride Thursday, and Friday he accepted three mounts -- one for the star Triple Crown trainer Bob Baffert and two others for the fellow Hall of Famers Bill Mott and Nick Zito.
"We've been together for a long time, and he has a comfort level on a horse that makes them better," said Mott, who with Bailey campaigned Cigar, the 1995 Classic winner and a two-time horse of the year. "He could keep riding for as long as he wants to."
In fact, it may be difficult for Bailey to retire if he wins several races, or at least gets his fifth Breeders' Cup Classic victory. There also may be the temptation to return if First Samurai lives up to his billing as the early favorite for the 2006 Kentucky Derby.
"He's immensely talented, but I haven't even thought about that," Bailey said. "I'm not going to let one horse here or there determine that. I'm just going to get through the Breeders' Cup, and in November I'll sit down and think about it."
Bailey has always been a methodical thinker. The quick and often winning decisions he makes on the racetrack come from hours of poring over the past performances of horses in the Daily Racing Form and from watching videotape to study the behavior horses and jockeys.
He is more selective in the mounts he takes, aiming for the Triple Crown and premier races for older horses.