This article is an inquiry into the work of educators at the James Baldwin School (JBS), a New York City public school with an explicit commitment to democracy in its mission and core values. The author was founding principal at JBS for the first six years, has stayed in touch, and recently went back to talk with faculty about how their work has evolved. JBS is only one of many in a long history of schools striving to ensure that the institutions charged with preparing youth for citizenship in a democracy function themselves in democratic ways. Past or present, and wherever they may be, in an era when elected officials across our country show authoritarian leanings, the work of schools that strive to function democratically demand careful consideration by educators, learners, and leaders in all corners.