This contribution to the Merritt Lectures is a presentation outline and accompanying “Underpinnings.” An important premise, reflective in the essay itself, is that philosophy for democracy is best served as a form of contemporary conversation: Its 2019 context is both significant and illustrative of a particular American pragmatist perspective. The essay is organized in three sections, historic background and then a current social and political context that point to a potential turn to youth from citizen education. The philosophical perspectives of John Dewey and Richard Rorty form a background that sheds light on a polarized and tribalized nation in which people are deeply divided over how government does and should govern their lives. Among issues, voter suppression is significant. To combat this early twenty-first-century situation and prepare for a future, activism by today’s youth provides a possible lesson.