What kind of conversation would Machiavelli have with one of the philosophers we studied previously (Plato, Xenophon, Augustine, Al-Kindi)? How would they question or criticize Machiavelli, or vice-versa

What kind of conversation would Machiavelli have with one of the philosophers we studied previously (Plato, Xenophon, Augustine, Al-Kindi)? How would they question or criticize Machiavelli, or vice-versa