This article problematizes leadership ethics in the context of a duress situation, using the concept of dirty hands. Comparative historical case study material from the German Occupation of the British Crown Dependencies of Guernsey and Jersey in the Second World War showcases how dealing with the incumbent leadership challenges posed by duress can be ethically optimized. The article argues that this is related to the management of social capital and legitimacy. The article's relevance to global leadership is owed to the fact that globalization increases gray zones and, with it, the likelihood of dirty hands reflexes. It contributes to an ongoing historical turn in management studies, through its advocacy of the historical method.