This study offers an extended reading of the most famous epistolary dialogue of the Renaissance, the letters exchanged from 1513 to 1515 by Niccolo Machiavelli and Francesco Vettori. John Najemy reveals the literary tensions of the correspondence, the importance of the dialogue with Vettori to Machiavelli's emergence as a political theorist, and the complex relationship between the letters and Machiavelli's major works on politics.