Jess Jackson, the founder of the Kendall-Jackson winery who won three straight Horse of the Year titles with Curlin (2007, 2008) and Rachel Alexandra (2009), died Thursday of cancer at his home in Geyserville, Calif. He was 81.

Credited with popularizing Chardonnay in America in the early 1980s, Jackson was inducted into the Vintner’s Hall of Fame in 2009. A lifelong racing fan, he began racing his own horses in 2003 under the nom-de-course Stonestreet Stables and breeding them on his Stonestreet Farm in Kentucky.

In the winter of 2007, Jackson purchased a majority interest in the 3-year-old colt Curlin, who went on to win the Arkansas Derby, Preakness, Jockey Club Gold Cup and Breeders’ Cup Classic en route to Horse of the Year. He earned that honor again in 2008 with victories in the Dubai World Cup, Stephen Foster, Woodward and Jockey Club Gold Cup to become the richest racehorse ever in North America with earnings over $10 million.

In the spring of 2009, Jackson bought the 3-year-old filly Rachel Alexandra after her victory in the Kentucky Oaks. She then won the Preakness, Mother Goose, Haskell and Woodward to clinch Horse of the Year.

Jackson is survived by his wife, Barbara Banke, five children and two grandchildren.