The “fall” of Lucrezia in Machiavelli's play La Mandragola is a puzzlement. She is presented as an intelligent and virtuous wife who by play's end not only agrees to commit adultery but murder as well. Any attempt to interpret the play must address the significance of Lucrezia and her fall. It is argued here, however, that the real deception is that Lucrezia does not undergo a conversion—she is of questionable character from the start. Upon examination, her similarity with the Goddess Fortuna reveals a deeper tale being told within the play. Machiavelh uses her to mock the Church, and St. Augustine in particular, and to deliver a frightening message that the free will is no match for the goddess.