If we compare it with the fellow notion of liberty, equality has an ambivalent place in modern political thinking. Whilst it counts as one of the fundamental norms, many think that equality is valuable only as a way to realise some features of liberty. I take a historical perspective on this issue, and try to identify some of the pre-modern roots of such an ambivalent attitude towards equality. I do this by using Jacques Rancière’s political model as an analytical framework and by taking a visual route, focusing on classical iconographic representations in which equality was present in the images’ subtexts. Ambrogio Lorenzetti’s allegory of good government is one iconic exposition of equality as a positive condition of civil peace. Already there, however, the positive value of equality is counterposed to the figure of violent retributive justice. Similarly, in the Christian narrative, equality is endorsed as the original condition of creatures under God, but is also associated with violent death. This signals one pre-modern root behind the ambivalence towards equality, particularly when the latter is understood dynamically, as levelling. Such a reversal of value finds an apotheosis, I suggest, in the revolutionary icon of the guillotine, a dramatic representation of equalisation that had a strong influence on modern political thinking. In J. E. Millais’ first painting, of Jesus in the House of his Parents, I find a more positive legacy of Christian equality in modern political thinking.