This article explores how Donald Trump capitalized on the right's decades-long, carefully choreographed and well-financed campaign against political correctness in relation to the broader strategy of 'cultural conservatism.' It provides an historical overview of various iterations of this campaign, discusses the mainstream media's complicity in promulgating conservative talking points about higher education at the height of the 1990s 'culture wars,' examines the reconfigured anti-PC/pro-free speech crusade of recent years, its contemporary currency in the Trump era and the implications for academia and educational policy.