While building his $200 million thoroughbred horse racing empire, Jess Jackson took on the same role of vocal outsider in Kentucky that he had brought to his beginning years in Wine Country.
He filed lawsuits and collected at least $4.65 million in settlements from advisers who had taken secret commissions on horse deals. And because the practice was legal in Kentucky, Jackson successfully lobbied the state Legislature to ban it.
"You don't come into an industry wanting to disturb anything," Jackson said in a 2008 interview. "But when you find there are aspects of the industry that need moral cleansing, you have to speak out."
He brought his single-minded drive and skills as a trial attorney to horseracing.
"Unfortunately, I had to do that in the wine industry, and I've found the the horse racing industry has a subculture," Jackson said. "My background is that I'm not afraid to speak out when I think something should be done."
Friend and attorney Fred Furth said Thursday that Jackson's campaign to clean up the thoroughbred horse trade was an example of how he could be relentless in fighting for what he thought was right.
"He had the guts to stand up for the principle of fair dealing," Furth said.
Jack DeMeo, a Santa Rosa attorney and racehorse owner, wasn't surprised by Jackson's assault on tradition.
"He probably didn't make a whole lot of friends in Kentucky," DeMeo said in 2007, "but that's probably not important to him."
Jackson did, however, make a mark at the track.
Curlin and Rachel Alexandra, his two equine superstars, captured horse of the year honors in three straight years, 2007 to 2009. They each won once at the Preakness Stakes, a Triple Crown event (Curlin in 2007; Rachel Alexandra, a filly, in 2009).
The two retired racers were bred in February at a Kentucky farm, beginning Jackson's bid to create what he called a "super horse."