Curricular questions of what and how knowledge should matter take on particular urgency when the knowledge at stake refers to cultural devastation in history. Whereas narratives of progress and discourses of "protecting the child" continue to dominate the public imaginary, a number of curriculum theorists have begun to explore the multiple ways in which educators have and continue to represent such histories in the classroom. This emergent literature offers a theory of pedagogy not as a set of skills to apply, but a way of asking questions about the ethical obligations, ontological crises and anxieties at work in efforts to teach and learn from difficult histories. My article elaborates on the problem of uncertainty from the vantage of two psychoanalytic thinkers who are also interested in the work of introducing the child to a world that fails: D.W. Winnicott's discussions with mothers on the problem of "disillusionment" and Jonathan Lear's discussion of "radical hope." In bringing together these examples, I offer a theory of education that articulates what is hopeful about the capacity to tolerate the disillusionment of both learning from and living in difficult times. At stake is a model of history education that can survive the disillusion of the promise of certainty and still dream of tomorrow.