Jess Jackson's high-stakes play

In a back room devoted to horse racing on 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 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 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 and cruises to victory at the Breeder’s Cup, Jackson, who witnessed seven of Curlin’s eight races in person, is seemingly back at Belmont.

“This is like a vacation,” he said. “I’ve never watched these races all together.”

Eventually, Curlin’s most recent race is run. The screen is blank.

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

But Jackson, the 553rd richest person in the world according to Forbes, 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.

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

But Jackson isn’t worried about his pocketbook.

If Curlin wins in Dubai, he would creep within about $1.3 million of passing Cigar as the all-time winningest horse. Cigar earned $9,999,815.

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

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 began in 1982 with an 80-acre vineyard in Lakeport.

And it also exlains 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.”