The story of self-made billionaire Jess Jackson, who put Chardonnay on America’s tables as he built the Kendall–Jackson wine empire from a few mountainous acres of grapes, and raced the Horse of the Year three years in a row, is a remarkable tale of romance, risk, and reinvention—perhaps the greatest second act in the history of American business.

Jess Stonestreet Jackson was one of a small band of pioneering entrepreneurs who put California’s Wine Country on the map. His life story is a compelling slice of history, daring, innovation, feuds, intrigue, talent, mystique, and luck. Admirers and detractors alike have called him the Steve Jobs of wine—a brilliant, infuriating, contrarian gambler who seemed to win more than his share by anticipating consumers’ desires with uncanny skill. Time after time his decisions would be ignored and derided, then envied and imitated as competitors struggled to catch up.

He founded Kendall–Jackson with a single, tiny vineyard and a belief that there could be more to California Wine Country than jugs of bottom-shelf screw-top. Today, Kendall–Jackson and its 14,000 acres of coastal and mountain vineyards produce a host of award-winning wines, including the most popular Chardonnay in the world, which was born out of a catastrophe that nearly broke Jackson. The empire Jackson built endures and thrives as a family-run leader of the American wine industry.

Jess Jackson entered the horseracing game just as dramatically. He brought con men to justice, exposed industry-wide corruption in court and Congress, then exacted the best revenge of all: race after race, he defied conventional wisdom with one high-stakes winner after another, capped by the epic season of Rachel Alexandra, the first filly to win the Preakness in nearly a century, cementing Jackson’s reputation as America’s king of wine and horses.