Judith Shklar’s dictum, ‘the worst evil of cruelty’, is well known. What this means for her political theory and how such theory is construed are rarely explored. This article maintains that Shklar’s turn towards cruelty/suffering has a specific role in the development of her political argument. It allows her both to curb her long-standing skepticism, and to use it creatively. This is because suffering must be examined from the perspectives of history and philosophy, which produce two sets of knowledge, each (...) limiting the overbearing tendencies of the other. The way Shklar uses the tension between history and philosophy for progressive purposes, and her idea that politics can mediate between history and philosophy, makes her a very contemporary theorist, similar to those who critically engage foundationalism without wanting to dispose of it completely. Approaching Shklar’s ‘Putting Cruelty First’ through her engagement with history and philosophy, and making use of the concepts of ‘realism’ (Bernard Williams) and ‘weak ontology’ (Stephen White) to do so are a more productive route to understanding her dictum than the usual one of examining it through the prism of her ‘liberalism of fear’. (shrink)