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The Gossip Girl
December 07, 2009
A rebellious, free-spending owner, a lightning-rod trainer and a homespun jockey helped turn undefeated filly Rachel Alexandra into the talk of the track in 2009
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December 07, 2009

The Gossip Girl

A rebellious, free-spending owner, a lightning-rod trainer and a homespun jockey helped turn undefeated filly Rachel Alexandra into the talk of the track in 2009

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This is a story about a racehorse who ran faster than all those she faced. It is the story of a filly the color of morning coffee, with a little girl's name and a gait so sweet that she seemed to run on clouds. It is the story of how one sublime athlete intersected everything that is good and bad in her sport, defining horse racing as it fights for life, its glory days as distant as dinosaurs. It is a story about speed, courage, passion and greatness. It is also about ego, jealousy, stubbornness and the dark corners of the game.

There is a billionaire horse owner named Jess Jackson, who came to racing late and has challenged tradition with a big checkbook and a bigger personality. He has bought expensive animals and shined a bright light on corruption and drug use, doing each with such flair that his stodgy peers sometimes wonder whether all the fuss is about the man and not the sport. "He does good things for racing, but he does them with his might and his power," says Satish Sanan, a former partner of Jackson's who also fights for racing reform but more quietly. "There is no doubt many people resent him."

There is the billionaire's trainer, Steve Asmussen, a prolific winner but a walking paradox. He is intensely committed to the equine breed, coming from a family that has devoted itself to horses for three generations, yet he is frequently found to have violated medication rules. "I have a lot of respect for him; he's a great trainer," says a rival trainer. "But here's a guy who's always in trouble."

There is a 43-year-old Cajun jockey, Calvin Borel, who is not on any expert's short list of the best in a brutal profession yet who has won two of the last three Kentucky Derbys and rode the filly to every one of her victories this season while under intense pressure to prove himself worthy, since the billionaire and his trainer customarily use another rider on their best horses. Some call Borel a savant. "Oh, shoot, I don't know about that," he says. "I know I accomplished more than I ever thought I would this year."

Finally there is a nearly flawless racing machine, a perfectly balanced 1,100-pound animal with the elusive combination of speed and stamina that breeders chase like the grail. She is Rachel Alexandra, named for the 13-year-old granddaughter of her original owner. Rachel made herself known to the public last May, on the day before the Kentucky Derby, when she won the prestigious Kentucky Oaks (for 3-year-old fillies) by a record 20¼ lengths. Fifteen days later, after Jackson had purchased her, she became the first filly in 85 years to win the Preakness—despite having changed barns, jockeys, grooms, exercise riders, diet and pretty much everything else in her life in the intervening two weeks.

She would finish her season unbeaten in eight races at seven tracks in six states. In August she dismissed Belmont Stakes winner Summer Bird by six lengths in the Haskell at Monmouth Park. A month later at Saratoga she closed out her campaign by becoming the first filly to win the Woodward Stakes in its 56-year history. She beat seven older males by a desperate head, exhausted from leading the race and from everything else that had come in the months before.

But for Asmussen, Rachel Alexandra defined herself in a quieter time, on an August day long before the sun rose. "I remember watching her breeze one morning at Saratoga," he says. "It looked like she could have left the ground, like she could have levitated. And then you look at her record: It's as if every time she ran, people said, 'That's never been done.' How can you do so many nevers?"

The sun is too warm and the sky too clear for a November afternoon in central Kentucky's horse country, where hillsides are divided into paddocks by miles of fencing. Skeletal trees line the roadways at Stonestreet Farm, the 465-acre property Jackson bought for $17.5 million in 2005 and christened with his middle name.

Jackson, 79, is worth $1.85 billion; he is the 193rd richest American (right above Dallas Cowboys owner Jerry Jones), according to Forbes magazine. As he walks from his office to a lunch prepared by his personal chef, he tells of riding horses on his grandmother's ranch in Texas and going to races with his uncle in the 1950s. The former taught him to ride, the latter to handicap. He wears a tweed hat, as he has often done since undergoing chemotherapy in 2008 for skin cancer.

Jackson was a property rights lawyer in San Francisco when in '74 he bought an 80-acre parcel that would grow into Kendall-Jackson Wine Estates. "You could call me a farmer," he says, "but also an entrepreneur." Three decades later, wealthy beyond his dreams, Jackson plunged headlong into the thoroughbred business. At one sale alone in 2004 he spent just under $22 million buying 95 horses.

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