No contemporary intellectual historian has produced more influential reflections on the historian's craft than Hayden White and Quentin Skinner, yet their legacy has never been meaningfully compared. Doing so reveals a surprising complementarity in their approach, at least to the extent that Skinner's stress on recovering the intentionality of authors fits well with White's observation that irony is the dominant rhetorical mode of historical narrative in our day. Irony itself, to be sure, has to be divided broadly speaking into its dramatic or Socratic variants and the unstable and paradoxical alternative defended by poststructuralist critics. The latter produced in White an anxiety about the anarchistic implications of an allegedly inherent undecidability in historical interpretation and narration, which threatened to conflate history entirely with fiction. By recovering the necessary role of intentionality as a prerequisite for a more moderate version of Socratic and dramatic irony—in which hindsight provides some purchase on a truth denied actors at the time history is made—it is possible to rescue an ironic attitude that can register the frequency of unintended consequences without surrendering to the conclusion that no explanation or interpretation is superior to another. Against yet a third alternative, which tries to reconstruct the past rationally as a prelude to the present, acknowledging the ironic undermining of intentions avoids giving all the power to the contemporary historian and restores a dialogic balance between actors in the past and their present-day interpreters.