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 organized 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-imperialist 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 embodied 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.