The second period of Machiavelli’s life was spent in the service of the free Republic of Florence, which flourished, as stated above, from the expulsion of the Medici in 1494 until their return in 1512.
After serving four years in one of the public offices he was appointed Chancellor and Secretary to the Second Chancery, the Ten of Liberty and Peace.
Here we are on firm ground when dealing with the events of Machiavelli’s life, for during this time he took a leading part in the affairs of the Republic, and we have its decrees, records, and dispatches to guide us, as well as his own writings.
A mere recapitulation of a few of his transactions with the statesmen and soldiers of his time gives a fair indication of his activities, and supplies the sources from which he drew the experiences and characters which illustrate The Prince.
His first mission was in 1499 to Catherina Sforza, 'my lady of Forli' of The Prince, from whose conduct and fate he drew the moral that it is far better to earn the confidence of the people than to rely on fortresses.
This is a very noticeable principle in Machiavelli, and is urged by him in many ways as a matter of vital importance to princes.
In 1500 he was sent to France to obtain terms from Louis XII for continuing the war against Pisa: this king it was who, in his conduct of affairs in Italy, committed the five capital errors in statecraft summarized in The Prince, and was consequently driven out.
He, also, it was who made the dissolution of his marriage a condition of support to Pope Alexander VI; which leads Machiavelli to refer those who urge that such promises should be kept to what he has written concerning the