Think Machiavelli was only about politics? Think again. This episode explores his scandalous and brilliant comedy, La Mandragola. We delve deep into its themes of deception and self-delusion, examining how external manipulation preys on internal weaknesses, much like the political strategies outlined in The Prince. Follow the schemes of Ligurio, Callimaco, and Friar Timoteo as they target the foolish Messer Nicia and the complex Lucrezia. We directly address the challenging question: Can a morally ambiguous work from a controversial author achieve literary greatness? Evaluating the play's artistic merits and considering the complex relationship between art and morality, we conclude that La Mandragola's power lies in its cynical yet insightful portrayal of human nature and the effectiveness of pragmatic action, securing its place as a work of enduring literary significance.