But he prefers his politics a lot less passive: The 69-year-old retired multimillionaire is now betting that he can pick political winners and losers back in his native Missouri.
Sinquefield is among a small and little-known, but powerful, group of big-money donors who have shied away from national politics to advance pet policy issues in their home states. In Missouri, where the hundred-dollar campaign checks that were long the norm are being replaced by Sinquefield’s six-, seven- and even eight-figure donations, he has fundamentally transformed the state’s sleepy politics in less than a decade. And he is not shy about advertising that fact: In January, as he wrapped up a lecture to a gathering of his fellow Chicago alums, Sinquefield offered a final takeaway from his recent experience in politics. “If you get involved at the local level,” he said, “you will be amazed at how much influence you can have.”
Amazed indeed—especially given Sinquefield’s humble roots. Unlike Charles and David Koch, the better-known GOP donors who inherited their father’s oil-and-gas fortune, Sinquefield carved his own path. The St. Louis native, who spent his early years in a local Catholic orphanage and even considered entering the priesthood, went on to study under famed University of Chicago economists Eugene Fama and Merton Miller, Nobel Prize winners known for their “let the markets sort it out” views. He became rich in the 1980s when he co-founded Dimensional Fund Advisors—he won’t say how much he’s worth—but left the investment firm in 2005 after he says he grew “bored” with simply making money. Now, Sinquefield splits his time between his $1.7 million, 8,320-square-foot, century-old mansion in St. Louis and a 1,000-acre riverside estate in rural Osage County, where he keeps a fleet of vehicles and four houses. He’s taken a decidedly activist view of how to spend his money advancing his idiosyncratic passions: promoting chess, dismantling the traditional public school system and eliminating income taxes.