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After Machiavelli advanced the view that Christian morality is incompatible with political success, there was a flurry of critical responses by Catholic moralists. In their rebuttals of Machiavelli’s views, some of them argued that the active life of a statesman was perfectly compatible with Christian principles. This anti-Machiavellian stance became a pillar of Catholic orthodox thought. The present study inquires into Cervantes’ perspective on Machiavelli’s challenge to the Catholic tradition, as expressed in his posthumously published Persiles and Sigismunda (1617). While studies of this Byzantine novel have generally been overshadowed by work on Cervantes’ Don Quixote, recent scholarship on this much-overlooked work has shown that it is possible to draw from it Cervantes’s view of Counter-Reformation culture. According to some critics, the Persiles is a straightforward story about a Christian pilgrimage that ends in Rome.