Sinquefield has devoted many millions to the idea of eliminating income taxes and replacing them with sales taxes, but the effort has not progressed either at the ballot box or in the legislature. A ballot measure he bankrolled last fall to change teacher evaluation methods and weaken tenure proved so unpopular that the campaign backing it went dormant weeks before the election. It ended up getting only about a quarter of the vote. “I think he has bad instincts overall,” says Ken Warren, a pollster and political scientist at Saint Louis University. “He’s backed a lot of causes that simply lose.”
But while Sinquefield’s batting average isn’t as high as he’d like, he has had some game-changing victories. After the failure on the tax veto override, Sinquefield and his squad tried again last year. That time, legislators succeeded in overriding a Nixon veto, offering Missourians their first income tax cut in nearly a century. Nixon complained publicly about spotting Sinquefield’s fingerprints on parts of the package. Ron Richard, the Republican leader in the state Senate, says Sinquefield deserves some, though not all, of the credit for pushing the tax cut through. “He has the ability and wherewithal to move ideas that need to be debated,” Richard says. Sinquefield devoted $10 million to Missouri candidates and campaign committees in 2014 alone, helping to support more than 160 campaigns.