Jess Jackson: A Visionary Vintner and Horse Racing Legend

Barbara Banke and Jess Jackson, second and third from left, hold up the Woodward Stakes trophy after Curlin won the race in 2008. (Eclipse Sportswire)

Type the name Jess Jackson into a search engine and chances are you'll skim across the term “billionaire.” While this brief description accurately sums up the late Jackson’s net worth — he ranked as one of the richest men in the world — such a simple one-word designation cannot even scratch the surface of Jackson’s depth as a businessman and sportsman.

In a manner reminiscent of the legendary King Midas, seemingly anything Jackson touched would turn to gold, and this applied wholeheartedly to his involvement in Thoroughbred horse racing.

Born Feb. 18, 1930, Jess Stonestreet Jackson, Jr. showed an interest in racing from a very young age; in fact, he spoke of watching the legendary Seabiscuit win the 1938 Bay Meadows Handicap, and counted Nashua, Native Dancer, and Swaps among the other great horses that he witnessed in action. But while Jackson did have an early involvement with the sport — racing horses with an uncle during the 1960s — Jackson’s focus was soon drawn to other endeavors; endeavors that would make him a legend in a completely different industry.

Initially working as a successful lawyer, Jackson became involved in the wine industry during the 1970s, growing grapes from an 80-acre pear and walnut orchard he purchased in 1974 to sell to wineries in California. In 1982, he co-founded the Kendall-Jackson Winery and proceeded to change the face of the industry by producing the highly popular Kendall-Jackson Vintner’s Reserve Chardonnay. So successful was the Kendall-Jackson Winery that Jess Jackson was inducted into the Vintner’s Hall of Fame in 2009.

Jess Jackson (Eclipse Sportswire)

Having amassed a fortune in business, Jackson had the wherewithal to pursue his passion for horse racing, returning to the sport in 2003 at the age of 73. Although it was relatively late in his life, when Jackson embraced the sport, he did so on a massive scale and achieved more in the span of eight years than most people achieve in a lifetime.

In 2005, he purchased a 469-acre farm in Kentucky for $17.4 million and named in Stonestreet Farms. He made a huge splash at public auction in 2005 when he spent more than $27 million on yearlings for Stonestreet Stables and broodmares for his Stonestreet Farms. Jackson also purchased an interest in 2004 Horse of the Year Ghostzapper, as well as Ghostzapper’s successful sire, Awesome Again.

Jackson bought in 2005 the established filly Forest Music, who proceeded to give Stonestreet Stables its first graded stakes victory when she won the Grade 2 Honorable Miss Handicap at Saratoga with an impressive display of speed.

While in the process of building up his racing stable and breeding operation, Jackson was also actively engaged in attempts to help reform and improve the sport. Calling for change on a variety of complex issues, Jackson helped to eliminate “dual agency” in Kentucky’s horse auctions, in which bloodstock agents representing buyers were receiving undisclosed commissions from both the buyer and the seller in auction transactions. He also called for the elimination of anabolic steroids in Thoroughbred horse racing, speaking on the subject at a 2008 congressional hearing and publicly backing up his stance by refusing to race his horses on steroids.

Two-time Horse of the Year Curlin (Eclipse Sportswire)

But Jackson might be best remembered for owning two horses that won a remarkable three consecutive Horse of the Year titles, thanks in great part to ambitious, sporting campaigns that Jackson orchestrated.

The first was Curlin, whom Jackson purchased as part of a partnership after the colt won his debut by 12 ¾ lengths in February 2007. After rewarding his new connections with victories in the Grade 1 Preakness Stakes, Grade 1 Breeders’ Cup Classic, and Grade 1 Jockey Club Gold Cup, Curlin was voted Horse of the Year at the 2007 Eclipse Awards.

At the Eclipse Awards ceremony, Jackson made the exciting announcement that Curlin would stay in training for 2008, an unexpected but generous decision given Curlin’s high value as a stallion prospect. The star colt went on to enhance his sterling record by winning four more Grade/Group 1 races, including the $6 million Emirates Airline Dubai World Cup (in which he raced completely free of medication), to earn a second Horse of the Year title and become the highest-earning North American-based racehorse in history.

Jackson returned to the spotlight in 2009 when he purchased a majority interest in Kentucky Oaks winner Rachel Alexandra for a sum reported to be in the $10-million range. Under Jackson’s management, Rachel Alexandra embarked on one of the greatest winning streaks by any 3-year-old filly in history, defeating males in the Grade 1 Preakness Stakes, Grade 1 Haskell Invitational Stakes, and Grade 1 Woodward Stakes to be named 2009 Horse of the Year.


Jackson continued to reap the success of his racing stable until his death from cancer on April 21, 2011. His passing came less than a year before the much-anticipated birth of a colt by Curlin out of Rachel Alexandra, the result of a mating planned by Jackson when he purchased Rachel Alexandra. In a tribute to Jackson, the colt was eventually named “Jess’s Dream,” and—fittingly—the colt won his debut on Aug. 24, 2015 at Saratoga, the same track where his illustrious sire and dam each won the Woodward Stakes.

In the years since Jackson’s death, his wife, Barbara Banke, has taken over the management of Stonestreet and has remained committed to maintaining and enhancing the empire that Jackson created.

Banke and Jackson (Eclipse Sportswire)

The results have been nothing short of amazing—since 2011, Stonestreet has been the owner or co-owner of Grade 1 winners Carpe Diem, Cavorting, Charlatan, Dreaming of Julia, Good Magic (an Eclipse Award winner), Lady Aurelia, My Miss Aurelia (an Eclipse Award winner), Rachel’s Valentina (a daughter of Rachel Alexandra), Rock Fall, and Tara’s Tango, as well as an impressive roster of Grade 2 and Grade 3 winners.

Like Jackson, Banke has been an active participant in racing organizations and has done her part to help grow the sport. With Banke at the helm, Stonestreet Farms has offered opportunities for fans to meet Rachel Alexandra, in addition to offering a contest for fans to name Rachel Alexandra’s first foal. Banke also has served on the Breeders’ Cup Board of Directors since 2012.

Needless to say, the future of Stonestreet looks bright. Recent stable stars like Good Magic and Charlatan have enjoyed success at the highest level, while the Stonestreet Farms broodmare band reads like a “who’s who” of prominent mares, including the aforementioned Cavorting and My Miss Aurelia.

You could say that “Jess’s dream” lives on.

Note: This story was originally published in February 2017 and has been updated.

Fun Facts

  • Jackson’s middle name, Stonestreet, was used as the name of his racing stable and breeding farm.
  • Horses owned exclusively by Stonestreet Stables have more than 350 races through Feb. 17, 2021 and earned more than $25.4 million in purse money since 2005, and this does not include the horses that Stonestreet has raced in various partnerships.
  • Both Curlin and Rachel Alexandra were inducted into the Racing Hall of Fame, Curlin in 2014 and Rachel Alexandra in 2016
  • As a broodmare, Rachel Alexandra enjoyed success with her two foals. Jess’s Dream won his only race, while Rachel’s Valentina was a Grade 1 winner who finished second in the 2015 Grade 1 Breeders’ Cup Juvenile Fillies.

newsletter sign-up

Stay up-to-date with the best from America's Best Racing!