Many authors, both scholarly and otherwise, have asked what might have happened had Walter Benjamin survived his 1940 attempt to escape Nazi-occupied Europe. This essay examines several implicitly or explicitly "counterfactual" thought experiments regarding Benjamin's "survival," including Hannah Arendt's influential "Walter Benjamin: 1892-1940," and asks why our attachment to Benjamin's story has prompted so much counterfactual inquiry. It also explores the larger question of why few intellectual historians ask explicitly counterfactual questions in their work. While counterfactuals have proven invaluable for scholars in diplomatic, military, and economic history, those writing about the history of ideas often seem less concerned with chains of events and contingency than some of their colleagues are-or they attend to contingency in a selective fashion. Thus this essay attends to the ambivalence about the category of contingency that runs through much work in intellectual history. Returning to the case of Walter Benjamin, this essay explores his own tendency to pose "what if?" questions, and then concludes with an attempt to ask a serious counterfactual question about his story. The effort to ask this question reveals one methodological advantage of counterfactual inquiry: the effort to ask such questions often serves as an excellent guide to the prejudices and interests of the historian asking them. By engaging in counterfactual thought experiments, intellectual historians could restore an awareness of sheer contingency to the stories we tell about the major texts and debates of intellectual history.