According to the Plutarch, Alexander the Great offered to spare besieged Athens on the condition that Demosthenes, the leader of the anti-Macedonian party, be surrendered to him. Were the Athenians morally permitted to deliver Demosthenes to face certain death at the hands of Alexander? This question engaged a great number of late scholastic moral theologians. This chapter presents and analyzes the solutions that they offered to this moral dilemma, from Francisco de Vitoria onwards. I first present a number of philosophically unpromising lines of argument proposed in the early stages of the controversy. As the controversy evolved and matured, authors gravitated towards two core views, those of Luis de Molina and João of St Thomas (Poinsot). The latter argued against the former that Athens would be intentionally killing an innocent (Demosthenes) by surrendering him to Alexander. St Thomas conceded that this committed him to the view that Demosthenes would also be killing an innocent (himself) if he were to surrender of his own accord.