Reading a novel about a dying person and the people attending the dying, one can not only reflect upon the moral involvement between the literary characters depicted, but also upon the way in which the reader takes the position of a “bystander” in this scene. In two novels, The Death of Ivan Ilyich by Tolstoy and The Big Ward by the Dutch author Jacoba van Velde, this moral involvement can be interpreted as a form of “compassion”. Martha Nussbaum’s concept of “compassionate imagination” offers a perspective on the way in which the reader can be involved in this literary depiction of the dying. However, the Aristotelian criteria that Nussbaum proposes for the rational judgement of compassion and her ambitions that literature can “raise society’s floor” by developing “compassionate imagination” in readers, are difficult to apply to these specific cases. In comparing both novels, it is exactly the differences between them – the historical context and social classes depicted - that bring to light a problematic presupposition in Nussbaum, namely the a-historical universality in the compassionate involvement. A re-interpretation of one of the Aristotelian criteria for compassion leaves room for a “compassionate imagination” not based on a rational judgement but on a sense of shared vulnerability that is precisely evoked by the literary depiction of the dying.