Plutarch’s Life of Philopoemen and Life of Titus Flamininus are often overlooked in favor of Plutarch’s more famous subjects. However, this biographical pair uniquely treats contemporary figures on opposing sides of the conflicts of the early 2nd century BCE: Philopoemen as the last great Greek general fighting for freedom, and Flamininus as the Roman general whose actions brought about Greece’s subjugation to Rome. Reading these biographies through a post-colonial lens reveals Plutarch’s internal resistance to the Roman subjugation. I argue that, although Plutarch does not outwardly denigrate the Roman conquest, he uses Flamininus and his flaws to criticize Rome’s subjugation of Greece. He simultaneously shows a preference for Philopoemen and the cause of Greek freedom throughout both works. He not only praises Greece’s former glory, but also condemns Rome’s dominant position over Greece. Despite Plutarch predating the traditional subjects of post-colonialism, this act of literary resistance to the Roman occupation justifies a close reading of these texts through a post-colonial lens.