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There is a widespread consensus that urban warfare poses significant challenges for military leadership. In this paper I examine general ethical questions associated with the strongest gang model for urban warfare, proposed by David Betz and Hugo Stanford-Tuck. The paper eventually focuses on leadership responsibility. What are the particular ethical demands on small-team leaders in urban warfare? The claim I shall defend is that military leadership according to the strongest gang model requires a kind of leadership which is virtuous in a special sense. Such a requirement on character is not optional. But it is demanding.