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

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.

He has since become one of racing's most aggressive owners, campaigning not only Rachel Alexandra but also Curlin, a two-time Horse of the Year ('07 and '08). Some in the racing community praise his initiative in a sport struggling for visibility. "Lord knows our industry needs what he's brought," says Bill Casner, co-owner and chairman of WinStar Farm and a major breeder and racer in Kentucky. "He is a true sportsman."

Others begrudge Jackson the stage. Not long after he entered the sport, Jackson filed several lawsuits over the issue of "dual representation." In such practices, bloodstock agents dupe deep-pocketed newcomers by conspiring with sellers to artificially drive up prices, then split the overpayment. Jackson won settlements totaling more than $4.5 million from three parties. "I didn't need the money," he says. "I wanted to do what was right." But the lawsuits embarrassed the so-called Sport of Kings. "I experienced many of the same problems as Jess when I started in racing [in 1999]," says Sanan. "The difference was, I worked inside the system, and Jess sued everyone. That made people uncomfortable."

Jackson bought a controlling interest in Curlin before he ran in the 2007 Kentucky Derby and defied current convention by racing him for a full year at four. He bought Rachel Alexandra for an undisclosed price (reported at $4 million to $5 million, which Jackson says is "close") after she won the Oaks and set her off on a wide-ranging campaign, including three races against males, which her previous owner, Dolphus Morrison, had said he would not do. "We pushed her," says Jackson. "We haven't yet defined her." He adds that Rachel will run as a 4-year-old.

It was a historic campaign, yet Jackson rankled some traditionalists by announcing each of Rachel Alexandra's races by teleconference (such plans are usually revealed by a trainer in work boots standing in a pile of manure) and then by shutting down his filly after the Woodward rather than run her in the Breeders' Cup Classic on Nov. 7. That race was contested on Santa Anita's synthetic surface, which Jackson dismissed as "plastic."

The debate over synthetic surfaces consumes racing. But Jackson's decision was doubly controversial. Zenyatta, a magnificent 5-year-old mare, won the Classic with a bravura late-running performance for the 14th victory of her unbeaten career. There is buzz that Zenyatta will be voted Horse of the Year in part because she showed up at Santa Anita, her home track, but also because it gives voters a chance to punish Jackson.

Asmussen stopped in front of the filly's stall at Churchill Downs a few weeks ago and patted her neck. A big horse makes the barn, but she is different from the last big horse in so many ways.

"Curlin was extremely serious," says Asmussen. "I've never seen a horse like him on race day. But Rachel has a brilliance, a purity. She's more emotional. She's like 'Hooooo, I get to go run.' And she's so athletic. She can stand flat-footed and jump as high as the barn. I've never witnessed anything like her."

Asmussen, 44, talks about horses with a passion that isn't easily faked. His father, Keith, has been training and riding horses since before Steve was born. His brother, Cash, was a world-class jockey (a path Steve had hoped to follow until he grew far too tall). In 2008 Asmussen won the Eclipse Award for outstanding trainer after his horses won a record 622 races. His frequency in the winner's circle earned him the gig with Jackson.

But as with Jackson, there is another side to Asmussen's story. U.S. racing is trying to rid itself of a pervasive medication problem. Horses at all levels are injected with and fed a dizzying array of performance-enhancing substances—some legal, some not, some permitted in training but not on race day. Rules vary among jurisdictions, and there is no national racing commission. Jackson is among those leading a movement to make racing drug-free, as it is in Europe. And Asmussen is consistently among those trotted out as poster boys for all that needs to be fixed.

Since 1990, according to the Association of Racing Commissioners International, Asmussen has been sanctioned 82 times by state racing commissions. The vast majority of his transgressions have been penny-ante stuff, such as failing to have proper paperwork (a $100 fine). But he was also handed a six-month suspension in May 2006 when one of his horses in Louisiana was found to have 440 times the legal limit of Mepivacaine, a local anesthetic that numbs the legs, enabling a horse to run through injury or intense pain. The ban ended nine weeks before Jackson raced Curlin. Asmussen is appealing another six-month suspension in Texas, for using a metabolite of lidocaine, another anesthetic.

Asmussen sits in his tack room at Churchill Downs, tugging on the wool hat he needed when he arrived in the 35° predawn chill. He could offer explanations: The Louisiana horse, a 3--5 favorite sure to be tested postrace, had so much juice in her system that she was almost certainly shot up on race day. What trainer would do that? In Texas, with its zero-tolerance policy on lidocaine, Asmussen's legal team has argued that the amount detected was so small it couldn't have been injected. "They have blood samples in a freezer, but they refuse to test that blood," says Asmussen's lawyer Maggi Moss, also a prominent owner who has 11 horses with Asmussen. "We said, 'Test the blood. If there's lidocaine in there we'll take the six months.' But they wouldn't do it." Of course, explanations can sound like excuses to a public inclined to believe racing is inherently dirty.

"I have 300 [horses], 300 employees, a wife and three children, and I've got a lab in a basement somewhere?" the trainer says, his voice raised. "I've dedicated my life to this sport, and I'm going to risk losing the opportunity to train Curlin and Rachel Alexandra? Are you out of your frickin' mind?"

Asmussen argues that the breadth of his operation not only results in his horses' being tested more than any other trainer's but also leaves him vulnerable to sabotage by jealous opponents, and to veterinary errors. "Some people think they can beat me even though I've been doing this my whole life," he says. "They let you bet on this game, so people feel cheated. I say if you can't beat me, run against somebody else."

Jackson, for his part, has spoken before Congress on the need for a zero-tolerance policy on PEDs in racing, and in 2008 he ordered Asmussen to stop giving Curlin approved steroids. But he has stuck by his trainer. "I believe he has great skill," says Jackson, "and a great love for horses."

Here is what hurts most deeply: "All this talk about me and medication," says Asmussen, "and Rachel gets dragged down because of it. It's wrong beyond belief."

While Jackson and Asmussen deal with complex and challenging issues, Calvin Borel's life is a wonder of simplicity. On a recent morning at Churchill Downs he worked five horses for his brother Cecil, a trainer, then sat sipping coffee in his agent's car. "A little windy today, that's all," Calvin says. "But I love it out here."

Borel has been winning races since not long after he was discovered riding in Cajun bush tracks as a teenager. He has won nearly 4,700 races for more than $105 million in purses, according to Equibase. He has been successful for a long time, but in the last three years he has exploded. First he won the 2007 Kentucky Derby with a ballsy rail-skimming ride on Street Sense. Last spring at Churchill Downs he went low again to win with 50--1 shot Mine That Bird. "This is a hard race to predict," veteran trainer Todd Pletcher told Louisville's Courier-Journal after Mine That Bird's victory, "but I'll tell you one thing—Calvin Borel has it figured out."

He was aboard Rachel Alexandra for her first four wins in 2009. After she was sold he asked Jackson and his wife, Barbara Banke, if he could stay on her (Jackson and Asmussen customarily use Robby Albarado on their best horses), and that wish was granted. "I'm thankful to them for that," he says. "I worked 30 years to ride a horse like her." Borel ranks just 13th in career earnings among jockeys but is the only one to have climbed off a Kentucky Derby winner to ride another horse in the Preakness (and win), and the only one to sit down with David Letterman on CBS's Late Show, which he did before the '09 Belmont.

All of this might have led to mounts in the big races for A-list trainers. It has not for Borel. Though he was back aboard Mine That Bird for the Belmont, Hissam couldn't get him a second mount that day. They went to Saratoga, and Borel's only two victories of the meet came on the day of the Woodward. "We were trying all month," says Hissam. "All those big trainers have their own guys." Borel is viewed by some owners and trainers as a Churchill rider with quirky skills who got the break of a lifetime when Rachel's original trainer, Hal Wiggins, put him on her.

If Borel feels wounded, he hides it well. He has been the right man on the right horse in two of the last three runnings of the biggest race in America. He has sat astride one of the greatest fillies in history. He is engaged to be married. "I love my everyday life," he says. "I love to win a $2,500 race at Churchill. I love to find a good 3-year-old for the big races. I'm lookin' right now."

Rachel Alexandra has been in her stall nearly every minute since early September, resting until training begins for her 4-year-old season, which Jackson plans to end at the Breeders' Cup at Churchill Downs next November. But on this day she is led into the midafternoon sunlight to have her picture taken. It is a combustible moment: a fresh racehorse led from her stall at race time.

After a minute of calm, she bursts forward, as if from the starting gate. Assistant trainer Scott Blasi desperately holds on to her lead. She drags him 50 feet along the grass before stopping. It's quite easy to see: Rachel just wants to run. Everything else be damned.

Now on SI.com

Mark Beech makes the case for Rachel Alexandra as SI's Sportsman of the Year, at SI.com/sportsman

If Borel feels wounded by his lack of mounts, he hides it well. "I love my everyday life," he says.

"Lord knows our industry needs what he's brought," one fellow owner says of Jackson.

"Rachel has a brilliance, a purity," says Asmussen. "I've never witnessed anything like her."

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Photograph by BILL FRAKES

BROWN BEAUTY In her stall at Churchill Downs, Rachel is the picture of serenity, but her trainer says he's never encountered a more athletic horse.

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Photograph by BILL FRAKES

SHOW JUMPER Two weeks after riding 50--1 shot Mine That Bird to a Derby victory, Borel (in yellow) won the Preakness on Rachel.

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JEFF KAVANAUGH (PREAKNESS)

[See caption above]

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Photograph by BILL FRAKES

ICONOCLAST A relative newcomer, Jackson has galvanized the racing world with his crusades against corruption and doping.

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Photograph by BILL FRAKES

FILLY FANATIC Asmussen's impressive win totals earned him the gig as Rachel's trainer, but his résumé isn't unblemished.