Recent debates among historians and in public have concerned the links between German colonialism and imperialism before the First World War and the Nazi regime and its crimes. This article analyzes the career of Franz Heinrich Witthoefft, a Hamburg merchant who shaped pre-1914 imperial expansion and interwar liberal internationalism—and sought to do the same with Nazi empire.  It argues that empire’s strongest legacy was its absence, an absence that created ambivalent possible futures and blurred the line between liberal and illiberal avenues to German power and international order. This blurriness offers an end-run around problematical attempts to narrate Nazism as little more than an extreme expression of global patterns and around untenable notions of German exceptionalism.