The publication of the correspondence between Reinhart Koselleck and Carl Schmitt enables readers to assess the relation between the conceptual historian and his radically conservative mentor, a topic of some longstanding controversy. In this review essay, I discuss their correspondence in relation to Gennaro Imbriano's book on Koselleck, which also relies on the correspondence to argue that Koselleck gradually transcended his earlier Schmittian beliefs. I seek to capture the current state of scholarship regarding this particular issue and anticipate possible future developments in the field. Although they do not offer major revelations about Koselleck and Schmitt's relationship, the recently published letters add welcome nuance to earlier scholarly estimations thereof and show how Koselleck gradually assumed a more equal role in the exchange. The most fertile theoretical points in the letters pertain, first, to Schmitt's observations about the uniqueness of history and the repetition of key questions in history and, second, to Koselleck's remarks on the need for a proper theoretical basis for historiography, including readjusted historicism and criticism on the philosophy of history's ideological ramifications. Imbriano's book characterizes Koselleck as a systematic thinker of history's political aspect who differed from Schmitt in making the distinction between politics (as a regulating process) and “the political” (as a principle in need of containment). As I argue, this distinction is not sufficient to set Koselleck's moderate conservatism apart from Schmitt's radical conservatism because Schmitt also took both aspects into account. I also predict that future scholarship will display a balanced use of archival material that further clarifies the genesis of Koselleck's theorems, in turn directly serving historical theory by examining its emergence out of concrete historical, political, and intellectual contexts.