While their scope and method may differ, the (f)act of reckoning with—and taking advantage of—contingency renders rhetoricians and philosophers associates after all. In this regard, Aristotle and Blumenberg will be exemplary, hence provide the framework. Between these diachronic bridgeheads, close readings applying the nexus of rhetoric and contingency to a selection of (Early) Modern texts and authors are intercalated—among them La Celestina, Machiavelli, Shakespeare, Wilde, Fontane.