The final condemnation of poetry in Book Ten of Plato’s Republic is known for its enigmatic and contradictory arguments against Homer, tragedy, and imitative art as a whole. A close analysis reveals two opposed charges against Homer. While Socrates criticizes Homer’s poetry for depicting questionable accounts of civic morality as though they were true accounts, he criticizes the same poetry for drawing civic morality into question. This essay examines these opposed charges in light of the allegory of the cave and the discussion of dialectical education in Book Seven of the dialogue. Scholarly treatments of Book Ten have overlooked its references to the deceptions of the political cave and to the ensuing discussion of dialectical thought in Book Seven as a mode of liberation from that cave. In simultaneously supporting and subverting civic morality, the tragic element of Homeric epic raises questions central to Socratic political philosophy. Only by first examining this tie between Homer and Plato can their deeper rivalry be understood.