This paper explores the possibilities of working with White, working-class teacher education students to explore the "complex social trajectory" (Reay in Women's Stud Int Forum 20(2):225-233, 1997a, p. 19) of class border crossing as they progress through college. Through analysis of a course that I have developed, "Education and the American Dream," I explore political and pedagogical issues in teaching the thousands of teacher education students who are the first in their families to attend college about social class. Arguing that faculty in teacher education too often disregard the significance of deep class differences between themselves and many of their students, I propose that teacher education include coursework in which upwardly-mobile students (a) draw upon their distinctive perspectives as class border-crossers to elucidate their "complex social positioning as a complicated amalgam of current privilege interlaced with historic disadvantage" (Reay in Women's Stud Int Forum 20(2):225-233, 1997a, p. 25) and (b) complicate what Adair and Dahlberg (Pedagogy 1:173-175, 2001, p. 174) have termed a cultural "impulse to frame class mobility as a narrative of moral progress". Such coursework, I suggest, has implications for the development of teacher leaders in stratified schools. The paper draws upon the literatures on social class and educational attainment, on the construction of classed identities in spite of silence about class in public and academic discourse, and on pedagogies for teaching across class differences.