The paper considers what united and divided Benjamin and Horkheimer-Adorno in terms of their respective confrontations with the question of what it is to articulate the past historically. It presents their shared self-consciousness of the difficult task of responding critically to a problem conceived of as the entanglement of the concept of history with domination. For the problem imbues conceptualization itself and therefore threatens the value of the authoritative statements made in their own critical reflection on it. I show that these thinkers necessarily respond to the problem in confrontation with specific historical contexts: fascism, Soviet communism, German social democracy, and liberal democracy. The challenge they face is how to metabolize thinking in the midst of tendencies that disable it. I compare Benjamin's solution, the dialectical image, with Horkheimer and Adorno's solution, the recovery of critical reflection through the fragmentary writing of Dialectic of Enlightenment.