Jess Jackson, a man who knew how to pick winners, whether they were thoroughbred racehorses or vineyards, died of cancer Thursday at his wine country estate in Geyserville, Calif. He was 81.

Jackson was a wine industry visionary who developed the Kendall-Jackson brand, which popularized premium wines for the mass market and helped make the chardonnay varietal a household staple.

Friends and business associates described Jackson as a classic entrepreneur who had three distinct, successful careers, first as a San Francisco attorney and then as a skilled wine merchant whose 14,000 acres of wine grapes are among the largest private vineyard holdings in America. In recent years, Jackson became a winning racing horse stable owner.

He spent millions of his wine profits building Stonestreet Stables and buying thoroughbred horses at auctions.

Jackson was co-owner of Curlin, voted Horse of the Year in 2007 and 2008. He also co-owned Rachel Alexandra, the filly that won the Preakness in 2009 and also was voted Horse of the Year.

And whether he was dealing in the horse or wine business, Jackson became known as an innovator unbowed by the conventional wisdom in businesses.

In 2009, he decided to have Rachel Alexandra skip the Breeders' Cup at Santa Anita over concerns about the Arcadia track's synthetic surface, referring to artificial surfaces as "plastic" and provoking a debate about the surfaces.

He was a vocal critic of special distribution laws that in many states require wine to pass through the hands of distributors, increasing consumer prices.

Jackson even challenged industry giant E.&J. Gallo Winery over trademark issues. He lost a legal battle over whether Gallo's Turning Leaf label too closely imitated the autumn-toned look and feel of his Kendall-Jackson brand.

Wine broker Bill Turrentine remembers meeting Jackson at a wine tasting in Santa Rosa decades ago. At the time, quality wine was sold by region. The label on each bottle would feature a geographic appellation such as Napa Valley that was the primary characteristic pitching the wine. But Jackson believed he could make flavorful and consistent wines by blending the same variety of grape grown in different regions.

"I remember thinking that this was another guy who better keep his day job as an attorney in San Francisco. The idea that you could charge a premium price for a bottle of wine that just said California on it was absurd," Turrentine said.

Jackson proved him wrong.

The rich, full-flavored chardonnay that Jackson's winery developed had just a touch of residual sugars that made it popular with yuppies and baby boomers just starting to discover quality wine, said wine industry consultant Jon Fredrikson of Gomberg-Fredrikson & Associates.

Jackson priced the wine about a dollar more than his other popular wines at the time, giving him better profit margins and funds to expand.

"He really believed this was a great model and said this was an opportunity that you could drive a truck through," Fredrikson said.

It launched Jackson into a busy acquisition spree.

"From about 1985 to about 1994, he was able to buy wonderful properties at very good prices, often below market," said Fredrikson, who often scouted the vineyards for Jackson. "There was a lot of risk there, but Jess had one commanding advantage over his competitors. He was a real estate lawyer who was very smart and knew how to get deals done."

Jackson wandered into the business as a weekend farmer after he bought an 80-acre pear and walnut orchard in Lakeport in rural Lake County in 1974 as a weekend retreat from city life and converted into a vineyard.

"I was attracted by the lifestyle. I wanted to get away from law and become a farmer," Jackson told The Times in 2007.