Driven to win: Jess Jackson's unconventional quest to make Curlin one of the all-time greats

In a back room devoted to horse racing at Jess Jackson's 5,310-acre estate in Geyserville, the career of a great racehorse -- Jackson's great racehorse -- was unfolding on a plasma screen.

There was Curlin, the reigning Horse of the Year, at Gulfstream Park in Florida 13 months ago. His first start. His first win. Says the announcer: "Curlin makes a mockery of the field."

Jackson smiles. He's seen this race 10 times.

For the next 30 minutes, Jackson, 78, the lawyer-turned-billionaire founder of Kendall-Jackson Wine Estates and 80 percent owner of Curlin, smiles often.

He is a self-made success not given to smelling the roses. But he is enjoying this look back at 2007, a year in which he took a ride many of his peers never will.

On the screen, Curlin wows them at the Rebel Stakes. And the Arkansas Derby. By the time Curlin wins the Preakness Stakes and the Breeders' Cup, Jackson, who has witnessed seven of Curlin's 10 races in person, is seemingly back at Pimlico Race Course in Baltimore.

"This is like a vacation," he said. "I've never watched these races all together."

After Curlin's most recent race is run, the screen goes blank.

And for most owners of accomplished Triple Crown Thoroughbreds, the story ends there. Keep racing? What for? The breeding shed -- and mega-millions -- await.

But Jackson, the 553rd-richest person in the world, according to Forbes magazine, can afford to take a risk. And the gamble he's taking now is turning heads in the horse-racing industry, a world he entered in 2003.

Millions be damned, Jackson is racing Curlin as a 4-year-old in an effort to send the horse, worth an estimated $40 million, into a stratosphere with the all-time greats.

"I want to establish Curlin for what I think he is," Jackson said. "He's one of the horses of the century."

Curlin's biggest chance to burnish his legacy arrives Saturday at the $6 million Dubai World Cup in the United Arab Emirates, the world's richest horse race. A victory would net $3.6 million, a pittance compared with the estimated $15 million he might generate annually in a breeding shed.

But Jackson isn't worried about his wallet.

If Curlin wins in Dubai, he would creep within about $1.2 million of passing Cigar as the all-time winningest horse. Cigar earned $9,999,815.

Focus on winning

Curlin's trainer, Steve Asmussen, admires Jackson's perspective.

Asmussen is handling 12 of the roughly 60 horses Jackson has in training. The horses are promising, but Asmussen doesn't expect any to enter a Triple Crown race this year. Jess Jackson doesn't just want to compete, Asmussen explains, he wants to win.

His focus on greatness explains his global wine company, which sprouted in 1982 from an 80-acre vineyard in Lakeport.

And it also explains why Curlin is still racing.

"I want to meet the person who would leave so much money on the table for the sport of seeing what their horse could accomplish," Asmussen said. "You know the saying, 'Put your money where your mouth is?' I'm not sure there's a better example than this."

There's a simple reason most owners don't put their money where their mouth is. There's far too much money to lose.

Breed or race?

Gary West, a veteran horse-racing writer at the Fort Worth (Texas) Star-Telegram, said the sport even encourages the early retirement of its stars, with its less lucrative payouts to older horses.

In the first four months of the racing season, 3-year-olds have 13 stakes races worth at least $500,000 each, including four $1 million races. Older horses have seven such races, with just one worth $1 million.

No wonder Curlin's main competition from 2007 -- stars such as Street Sense, Hard Spun and Any Given Saturday -- have all been retired.

Horse racing long has been dominated by commercial breeders fixated on dollar signs. And the focus away from the track has contributed to the sport's sagging appeal.

West said the situation is tantamount to NFL announcers being paid more than the players, a move that would send the league's biggest names to the booth prematurely.

In Jackson, however, he sees a maverick shaking up the staus quo.

"Jess Jackson has come along and said something is wrong here. We're focusing on the sale ring rather than the racetrack, and in doing so we're compromising greatness," said West, who has covered roughly 60 Triple Crown races since 1982. "There are many people within the sport who have the financial wherewithal to make the same decision, but they don't. Why? Are they afraid of being called bad businessmen?"

Jackson says other factors influenced him to race Curlin this year. Among them are generating fan interest, fostering international relations -- sending him to what he terms a "benevolent dictatorship" in Dubai -- and establishing the genetic traits of durability and stamina.

Something to prove

But he becomes most passionate when discussing Curlin's ability, which he aims to prove is once-in-a-generation by continuing to race him, particularly in Dubai.

"If he wins an international race, the English won't be able to claim they have three horses that are better than him. That's what they did last year," said Jackson, who proudly noted he is a 14th-generation American. "I'm an American, dammit, and I'm a patriot and I'll be damned. I'll match any horse that wants to run against him. The point is I'm a sportsman, too, and I don't like to have people denigrate my horse. Maybe he isn't the best. But let them put up or shut up. If they have someone that can beat him, we're taking the shot."

If Jackson has his dander up, it's not the first time since he entered the industry five years and more than $200 million ago.

In response to feeling defrauded by advisers when he began building his Thoroughbred breeding and racing operation -- he owns three farms in Kentucky and two in Florida -- he has successfully lobbied the Kentucky Legislature for a law banning undisclosed commissions on horse sales.

The practice of horse traders representing the buyer while also taking payments from the seller had been tacitly approved of for years. The newcomers to the sport who were bilked stayed silent, taking it as the price of initiation. Jackson sued.

Jackson recently settled with bloodstock agent Emmanuel de Seroux for $3.5 million. He previously reached settlements with three other bloodstock agents and a former trainer.

A vocal outsider

The episode is reminiscent of Jackson's start in the wine industry. He co-founded the Family Winemakers of California to give a voice to smaller wineries, who he believed were being bullied by the industry's giants.

Jackson is back in his role as the vocal outsider, a position he says he doesn't enjoy.

"You don't come into an industry wanting to disturb anything," Jackson said. "But when you find there are aspects of the industry that need moral cleansing, you have to speak out. Unfortunately, I had to do that in the wine industry, and I've found that the horse-racing industry has a subculture. ... My background is that I'm not afraid to speak out when I think something should be done."

Trainer Mike Orman, who was hired by Jackson last year to help rehabilitate injured horses, said Jackson is a one-of-a-kind figure in the sport. Orman, 65, has spent 40 years training horses, sending one to the Kentucky Derby and another to the Breeders' Cup.

"He's very unique in the business, and a lot of people don't like what he does," Orman said. "It's greed. He opened up a can of worms that had never been opened. And he made a lot of people mad. Give him credit. He stood his ground."

Advancing causes

Jackson has other causes. He wants the fragmented sport to adopt a Major League of Racing, which would unify it under one governing body. He is passionate about horse safety and speaks at length about the merits of a zero-tolerance drug policy and limiting the racing of 2-year-olds. He has supported legislation that would prohibit the slaughter of horses for pet food.

Whether his causes are advanced is uncertain. But his most visible cause -- the matter of Curlin and his legacy -- is likely to be successful, said Andrew Beyer of the Washington Post, the nation's foremost horse-racing writer.

Because Curlin didn't race until he was a 3-year-old, he spent last year playing catch-up with the competition. The playing field is different in 2008.

"For Curlin to do what he did in the Triple Crown and keep on going through the Breeders' Cup was a remarkable achievement," Beyer said in an e-mail. "This year, when Asmussen gets to plan a campaign instead of having everything forced by the schedule of the 3-year-old races, Curlin can do some very big things."

For his part, Jackson knows he was fortunate to witness the big things Curlin accomplished in 2007.

And as he recently watched Curlin on the plasma screen, roaring to victory at the mud-soaked Preakness and getting nipped at the Belmont Stakes, he relished recalling the highs and the lows.

For most owners, it was a once-in-a-lifetime year. But Jess Jackson has the backbone -- and the bankroll -- to try to do it all over again.

You can reach Staff Writer Eric Branch at 521-5268 or eric.branch@pressdemocrat.com.