Excerpt from Be Like the Fox: Machiavelli in His World by Erica Benner

I wanted to wait until I had a released copy of Be Like the Fox to quote anything from it. Here's a lengthy excerpt about an episode late in Machiavelli's life. The setting: the Medici successfully returned to Florence in 1512 and Machiavelli was removed from office. He remained in political exile until 1521 when he went on a mission to a Franciscan monastery in Carpi on behalf of the Florentine government. Benner shows the lighter side of Machiavelli on this mission. The italicized are quotes come directly from the mentioned letters.

[O]n arriving at the monastery, he is overwhelmed with gloom. A humourless little monk shows him to a dreary cell where he is to sleep. The food is bad, in equal parts bland, stale, and nasty; the company is much the same. His impulse is to ridicule it all, but there is no one there to laugh with him. ...

He could never wallow in humiliation for long. Now, instead, he'll try to make fun of his plight, his hosts, himself. After a long day of wrangling with his prolix, painfully tedious hosts, he writes to Guicciardini. Magnificent Governor. I am turning over some way in which I might stir up strife among these friarhoods so that they might start going after each other with their wooden clogs. His advanced age and outsider status have made him freer than most men he knows, or than his younger self, to indulge in pure silliness. Send me a servant, or a messenger, whose attentions would cause my reputation among these friars to swell. Bugger decorum.

The next day a crossbowman arrives, bearing a letter addressed to His Magnificence M. Niccolò Machiavelli, Florentine Nuncio, etc. That 'M.' is good, he thinks. He is neither a Messer—a qualified doctor of laws or medicine—nor a Monsignor, but these monks are vulgar enough to be agog at the faintest hint of a title. On seeing the martial-looking messenger and hearing whispers, 'To His Magnificence!' the friars spring up from their seats and swarm around their visitor, asking him what the news was. And I, he tells Guicciardini later that day, to heighten my prestige, said that the emperor was expected at Trent, that the Swiss had convened fresh embassies, that the King of France wanted this and that. Think he must be a diplomat of very great stature, they all stood around with their mouths hanging open.

Send a flurry of further dispatches, he implores Guicciardini. If those friars see dispatches arriving thick and fast, my shabby conditions here might improve.

Francesco, good man, gladly obliges. 'Though I'm not,' he writes, 'in the habit of performing such services without pay.' He promises to send a fresh crossbowman to Niccolò the following day with his shirt flying behind his hips, so that everyone will believe you are an important personage.

Their plot works wonders. Within hours, Niccolò has been given a better bed and much better meals. I gobble up enough for six dogs and three wolves, he reports to his co-conspirator. He revels in his new-found status. Even as I write this, he tells his friend, I have a ring of monks about me; they marvel and gaze at me as at one inspired. And I, to make them marvel even more, sometimes pause writing and breathe deeply. They absolutely begin drooling.
(269-270)

This is a guy I'd want to knock back some Tuscan wine with over a long evening.

Also: My notes on the book can be found here.