Following the extraordinary success of his Kendall-Jackson wines, vintner Jess Jackson is now pursuing his passion for racehorses. He invites F&W’s Lettie Teague to a down-home lunch at his Kentucky horse farm.

“Jess always tells me, ‘Don’t expect anything. Don’t get your hopes up,’ ” Barbara Banke, Jess Jackson’s wife, said to me as we stood in the Stonestreet Stables box at the Belmont Park racetrack in Long Island, New York. We were awaiting the start of the Jockey Club Gold Cup, in which Curlin, the winner of the 2007 Preakness and owned (80 percent) by Jackson, was a leading contender, though not the favorite. That distinction belonged to Lawyer Ron, a powerful chestnut just off a win at the prestigious Woodward Stakes earlier that month.

I found it hard to believe that one of America’s most successful vintners—a man who virtually created a new varietal category with Kendall-Jackson Vintner’s Reserve Chardonnay—would espouse the philosophy of low expectations. But then Jackson, according to his wife, could be surprisingly unsettled by a race in which he had a horse. And thus the 78-year-old was home in California (supposedly with the flu). “But you can be sure he’s watching it on TV,” Banke said.

Although Jackson is a billionaire a couple of times over (he’s number 432 on the Forbes list of the wealthiest people in the world), his entry into the rarefied realm of Thoroughbred racing has been fairly recent. It was less than four years ago that Jackson purchased two of the most prominent breeding farms near Lexington, Kentucky, and rechristened them Stonestreet. The name is a double homage; it’s Jackson’s middle name as well as the name of one of his best wineries.

Stonestreet is but one of more than 20 California wineries that Jackson and his family own under the label Jackson Family Wines. Theirs is the ninth-largest wine company in the United States, with a five-million-case production, though many of the wineries that comprise it are quite small. These include boutique properties such as Lokoya and Cardinale, each of which produces fewer than a few thousand cases of highly rated wine each year. Other well-known Jackson-owned properties include Matanzas Creek, Vérité and, most recently, Freemark Abbey, a Napa winery he acquired about a year and a half ago. (Jackson also owns wineries in Italy and France.)

No winery in the portfolio is more famous than Kendall-Jackson. Appearing in the winery’s ads looking very much like the hero of a Louis L’Amour western, Jackson is photographed in various idyllic settings, sometimes atop the word “truth,” which is one-fifth of the winery’s motto, “A Taste of the Truth.” The “truth” in this case refers to the wine’s authentic reflection of terroir, the location and circumstances under which wine grapes are grown—whether it’s a specific vineyard, as is the case with the wines of Kendall-Jackson’s Highland Estates label, or several regions, as with Kendall-Jackson’s Vintner’s Reserve wines, made with grapes from vineyards located throughout California.

There are 11 Vintner’s Reserve wines; the most renowned of which is the Chardonnay. The story of its creation is one of the world’s great winemaking legends. When it debuted in 1982, it was an immediate hit, thanks to a timely and supposedly accidental addition of residual sugar by then-winemaker Jed Steele. This made the wine a little bit sweeter than most Chardonnays, and also launched Steele’s career—not to mention sales of about two million cases a year.

Although it has taken Jackson almost three decades to amass his vineyards and wineries, he became a Thoroughbred owner of consequence in a much shorter period of time. That’s mostly thanks to Curlin, who ultimately won (by a neck) the 2007 Jockey Club Gold Cup race that Banke and I attended and, a month later, the 2007 Breeders’ Cup. Even more recently, he was named 2007 Horse of the Year at the Eclipse Awards—one of the highest honors in racing.

Horse racing has certainly brought Jackson greater fame and further, if unnecessary, fortune, yet he identifies himself as a horse breeder first and is far more likely to be found at the farm than the track. He spends about a week each month in Lexington, flying back and forth from California. It was in Kentucky that we first met, to talk about horses and wine.

“We are really more about raising horses than racing them,” said Jackson, a tall, handsome man with a senatorial thatch of white hair, as the three of us—Jackson, Banke and I—took a short tour of the farm. We followed the black wood fencing that encircles the 500 or so acres as we went to have a look at the foals, all fillies, that had gathered just outside the gray-shingled Chardonnay barn. (All Stonestreet barns are named after grapes.)

Banke held out a hand to a particularly winsome chestnut filly that she declared her favorite. “Her mother is Friendly Michelle, and her father is A.P. Indy,” she explained. Friendly Michelle was a great racehorse and A.P. Indy a true Thoroughbred legend—a son of Triple Crown winner Seattle Slew and 1992 Horse of the Year.

Jackson has studied Thoroughbred bloodlines for decades, though now perhaps more carefully than ever, as he has been buying well-bred horses nearly as rapidly as he has wineries. “You look for balance in a horse, just like you do in a wine,” he said, gesturing to the fillies before us. “When I see our foals move, I get a feeling for how efficient they are, how they hold their heads. It helps me decide which horses are worth investing in. But I’m a lot better at wine than horses.”

There are other, less appealing similarities between the two businesses, Jackson added as we walked. “There’s a lot of hyperbole in both industries,” he noted. Aiming to do his part to bring truth to breeding as well as wine, Jackson has an impressive legal team at work on several bills before the Kentucky state legislature. The topics include the licensing of bloodstock agents and greater transparency in horse sales. The latter is a personal issue for Jackson, who was defrauded of millions when he entered the business.

Legal wrangling is familiar to Jackson, who was a successful attorney in San Francisco (as was his wife) for many years before turning to the wine business full-time. But these are only two of the many jobs Jackson has held in his seven-plus decades. Others include stints as a policeman and a farmer. Jackson learned farming growing up in Depression-era Texas. It was there, he said, that he learned “how to milk a cow and shoot a gun and love animals, particularly horses.”

That love is much in evidence as Jackson walks around his farm, talking to a horse here and there. Remarkably, for a man so worldly and accomplished, there is in his face still a kind of wondering awe. This is particularly apparent as Jackson speaks of the hope that takes hold each spring, when every breeder in Kentucky and far beyond imagines himself in possession of that most elusive thing—a Derby horse.

But the Kentucky Derby is still many weeks away when Jackson and Banke invite their friends Angela and Antony Beck to an alfresco lunch at their farm. The Becks are a handsome, fortysomething couple who own Gainesway farm a few miles down the road, where famed stallions like Afleet Alex and Birdstone stand stud. The Becks also make wine. Antony’s father, Graham, a coal miner turned multimillionaire, founded Graham Beck Wines in South Africa in 1983 and purchased Gainesway six years later.

The two families have talked off and on about making a wine together, said Antony Beck, as Amber Huffman, the Jackson family chef, filled his glass with 2006 Kendall-Jackson Vintner’s Reserve Riesling and handed him a square of toasted bread topped with a blend of melted cheese and beer—a Kentucky horse-country classic. The spring menu reads like a roll call of Jackson family favorites, all paired with Kendall-Jackson Reserve wines: chicken and sausage gumbo over rice with dill-flecked biscuits (paired with Chardonnay); tangy barbecued shrimp with cheese grits (and Pinot Noir); and finally, an impossibly rich chocolate bread pudding with bourbon-caramel sauce (and Cabernet Sauvignon). As they passed around plates and glasses, the friends talked of a time in the future, perhaps even in the next several years, when the offspring of Afleet Alex and Birdstone will be ready to race. Perhaps the Jacksons and Becks will not only produce a wine together someday, but a Derby winner, too.

In the meantime, Jackson is doing all he can to make Thoroughbred racing more democratic. “I would like to have a horse like John Henry or Swaps or Seabiscuit,” he says, naming the legendary American horses who fans, mostly poor or middle-class, followed as avidly as people today do basketball stars. “Horses like that appealed to the common man.”

It’s not a surprising ambition for a man who has devoted himself to making wine a more populist drink. But at the same time, Jackson acknowledges that it will be a lot more difficult than convincing people to drink Chardonnay. “In the wine business, at least you know the soil is always there,” Jackson said. “Wine is a piece of cake compared with Thoroughbred racing.”