Borel—friends still call him by his childhood nickname of Boo, short for Boo-Boo because he was born long after his next-youngest sibling—started riding on Louisiana's bush tracks before he was 10. He dropped out of school in eighth grade. "He was a natural rider," says former trainer Virgil (Yu Yu) Blanchard. "Nine years old and he stayed so calm on those horses." Borel was racing professionally at 16, having developed into a solid rider, just below the very top. Then in the first week of November 2006 he won the Breeders' Cup Juvenile on Street Sense at Churchill Downs, establishing that horse as the Derby favorite.
Nineteen days later Borel went down on a 3-year-old gelding named Pew and shattered his right wrist. He underwent surgery to implant eight screws and a plate. More significant, during his hospital stay he stopped the forced vomiting—flipping, in jockey parlance—that he had used to control his weight for more than two decades.
"He felt good not heaving," says Funk. "And then in the hospital a nutritionist came to see him and said, 'You don't have to do this to yourself. There are other ways.'" Funk started cooking healthier meals for Borel, and 11 months shy of his 41st birthday, he stopped flipping. (Borel still sweats off excess pounds every day in the jocks' steam room.)
Borel won the 2007 Kentucky Derby on Street Sense and that year rode the entire lucrative Saratoga meet for the first time. But he still didn't crack the top echelon, and instead became known for tirelessly working horses every morning and riding cheap long shots in the afternoon with the same fearless vigor as expensive stakes horses. Last Nov. 29 Wiggins put Borel on Rachel Alexandra for the Golden Rod Stakes at Churchill Downs, and she set a stakes record while winning by 4¾ lengths. The filly, always with Borel on board, has not lost since.
Morrison had numerous chances to sell Rachel Alexandra, but he didn't crack until Jess Jackson, 79, who founded the Kendall-Jackson winery, called him after Rachel won the Oaks by 20¼ lengths on the day before the Derby. "I suggested a pretty good number," says Morrison. "They tried to bring that number down a little bit. I said that's the number. They have a lot of money. And they agreed to it." (Morrison and Jackson have not disclosed the amount of the sale. Morrison told SI that a reported figure of $3 million to $4 million "wouldn't pay the tax on the actual cost." Wiggins, who was not privy to the exact price, said he had been told it was "10 to 12 million dollars.")
The sale was jarring. Jackson transferred Rachel to his regular trainer, Steve Asmussen. At 5:15 a.m. on Thursday, May 7, Asmussen and his assistant, Scott Blasi, walked Rachel the 200 yards from Wiggins's barn to Asmussen's. Wiggins and his staff were crestfallen. "The whole crew was walking around with their heads down," says Wiggins. "I called them together and said, 'Hey, we had a lot of fun with her. Sun's gonna keep coming up.'" He also immediately put another horse in Rachel's number 17 stall, so that his staff didn't have to look at an empty spot.
Morrison had said he would not run Rachel Alexandra against colts in the Triple Crown, but Jackson expressed a desire to enter the filly in the Preakness. "It's the only way we'll get to see her reach her full potential," said Jackson. "This way she has a chance to be a true champion." (He also would like to breed Rachel to Curlin, his '07 Preakness-winning colt.) Before gaining entry into last Saturday's race, Jackson and Rachel had to survive an unseemly attempt by several owners to block her entry, which was possible because the filly had not been nominated to the Triple Crown. Beyond that, after Eight Belles's death in the '08 Kentucky Derby, red flags are raised whenever fillies race colts.
Borel, meanwhile, worried that Jackson and Asmussen would pull him off the filly in favor of their regular rider, Robby Albarado. On the afternoon of the sale Borel collected his Derby-winning share of $141,720. Then he called Funk and told her, "I never thought I'd be holding a check for this much money and crying." Twenty-four hours later Borel's agent, Jerry Hissam, was informed that Jackson and Asmussen didn't intend to make a jockey change. Borel said he would ride her instead of the Derby winner, an unprecedented decision.
On the Wednesday before the Preakness, Rachel Alexandra drew the far outside post in the 13-horse field. Some saw this as useful for the filly. "I'd rather see her down inside where we kick some dirt in her face and push her around," said Gary Stute, who trains Papa Clem, who was fourth in the Derby and would finish sixth in the Preakness. Borel turned anxious, bearing the weight of the highest-profile dice roll any jockey had ever made. "We slept on opposite sides of the bed," said Funk. "He was just testy."
No need. Pimlico was calmed by a no-BYOB rule that reduced attendance from last year's 112,222 to 77,850, and Rachel arrived ready to perform. The outside position allowed Borel to utilize Rachel's quickness and athleticism—astounding in a big, tall filly—to take the lead, just two paths wide into the first turn. Even while running a crisp 46.71 seconds for the first half mile, fighting for the lead with Big Drama and struggling to take hold of the deep track, Rachel stayed relaxed. Into the stretch she opened a four-length lead and seemed poised to romp.