This paper reads parallel scenes in Herodotus and Thucydides to find a shared emphasis on flawed deliberation as the cause of catastrophic defeats for imperial powers. Both texts question the foresight and rhetorical strategies of self-styled wise advisers who ironically advance the very decisions they seek to forestall. Yet both authors also suggest that better strategies of advice could have altered the outcome. In contrast with those who read Herodotus and Thucydides as fatalists showing the futility of wise counsel in the face of imperial aggression, we find that they evince a belief in the constructive possibilities of advice.