During Machiavelli’s fourteen-year reign in office, he slowly gained a name for himself. The Italian philosopher was placed in charge of diplomatic correspondence of his bureau. He also served as Florentine representative on nearly thirty foreign missions. Also, attempting to organize a citizen militia to replace the mercenary troops was another one of Machiavelli’s roles. He obtained the surrender of Pisa, which had revolted and obtained independence for years.

In 1512, Machiavelli’s authority in Florence vanished. Julius II drove the French from Italy. The new citizen army that Machiavelli had organized could not withstand the power and force of the Pope’s prestige and his Swiss mercenaries. A treaty said that the state of Florence should return to Medici rule. Machiavelli, being the ex-gonfalonier’s man, was cut short of his office and exiled from the city for one year. "He then fell under suspicion, although unjustly, of being implicated in a conspiracy against the new government." (Benn, S.I.) He was sent to prison, tortured, and let go when Giovanni de Medici rose to the title of Pope.

At the time of Machiavelli’s release, his family, consisting of his wife and children, and himself moved to a small farm close to Florence. The only bond he had with the outside world was his confidant, the Florentine ambassador to the Pope. During the time on the farm, Machiavelli wrote many of his most famous writings, one, the Mandragola, was prosperous and was performed in front of Pope Leo X in 1520.