On the restoration of the Medici, he was arrested on a charge of conspiracy and after which he had to withdraw from public life. He devoted himself to literature, writing historical treatises, poetry, and comedies.

He is mostly known for his masterpiece 'The Prince', whose main theme is that all means may be used in order to maintain authority. Because he found it futile to pursue a political purpose by methods that are bound to fail, he explored the avenues which would be most successful to achieve and maintain power.

The book was condemned by the pope, and its viewpoint gave rise to the adjective machiavellian.