The most trenchant critiques of Western international law are framed around the legacy of its historic complicity in the imperial project of governing non-European peoples. International law organised Europe and its ‘others’ into a hierarchy of civilizational difference that was only ever reconfigured but never overturned. But when analysing the complex relationship between international law and imperialism the differences within Europe—as opposed to a dyadic opposition of Europe versus the ‘rest'—also matter. Within the historical and political constellations of the early and mid-twentieth century, German difference produced a set of arguments that challenged dominant discourses of international law by posturing as anti-imperial critique. This article focuses on the global career of Friedrich Berber (1898-1984) who, as a legal adviser in Nazi Germany and Nehru’s India, was at the forefront of state-led challenges to liberal international law. Berber fused notions of German civilizational superiority with an appropriation of Indian colonial victimhood, and pursued a shared politics of opposition. He embodies a version of German-Indian entanglement which did not abate after the Second World War, emphasizing the long continuities of empire, power differentials, civilizational hierarchies and developmental logics under the umbrella of international law.