This article compares the different ways in which, during the post-war decades, the Allied war crimes trials programme responded to the war criminality of two prominent German officials: Field Marshal Albert Kesselring and SS General Karl Wolff. It explores the question of why Wolff, whose complicity was arguably much greater than that of Kesselring, received more favourable treatment, and the role of various political and geo-political factors, including those influencing the interventions of US intelligence officials, as explanations for this apparent legal discrepancy.