The article starts from a thought experiment attributed to the Greek philosopher Carneades and handed down by Cicero and Lactantius. After a shipwreck, two seamen swim in the sea. There is a plank that promises rescue, but it has room for only one of them. The problem is that in this particular situation, the survival of one is only possible at the cost of the other’s life. This thought experiment, which is, in this instance, called the rescue or survival dilemma, has many intricate moral and juridical implications that require dis cussion. It is significant that what seems to be an intellectual experiment recurs in real-life situations throughout the ages. The first part of the article examines the discussion of the dilemma in question in philosophy from classical antiquity to modernity, with a special focus on Leibniz, whose importance in this tradition has been largely ignored so far. Since the rescue dilemma raises many legal questions, it is necessary to look at the way juridical discourse deals with it. The second part of the article investigates representative instances of the rescue dilemma in literature of the eighteenth and nineteenth centuries. Since philosophy and literature do share a deep interest in one and the same problem here, the investigation is concluded by reflections on the relative nature of discourse in the two disciplines and their different ways of dealing with significant human issues.