This paper considers the conflicting "loves" of Cornelius Castoriadis--his love for the ancients, and especially Plato, and for the common person of the demos. A detailed study of Castoriadis' analysis of Plato's Statesman exposes that Castoriadis attempts to resolve the paradox by rereading Plato as a radical democrat. I argue that this unorthodox reading is at best "quirky, " (a charge Castoriadis levels at Plato) at worst a groundless sophism. However, I conjecture that Castoriadis' reading may not constitute a serious attempt to describe a Platonic politics, so much as a prescriptive reading of what otherwise might have been, given certain strands of political generosity evident elsewhere in Plato's corpus.