In 1506, Machiavelli was made Secretary of the council of Nine, a group that controlled this militia. Then, in 1509, Florence went to war with Pisa. The militia was used in this battle, and Machiavelli was right there on the front lines, commanding his troops, against the wishes of the council. The militia helped take back the city under Florence's control. This result was a victory for Florence, as well as Machiavelli.
Another quality that Machiavelli refers to in The Prince is generosity. He writes that "it would be good to be considered generous, nevertheless, generosity, used in such a manner as to give you a reputation for it will harm you; because if it is employed virtuously and as one should employ it, it will not be recognized and you will not avoid the reproach of his opposite" (Machiavelli 41). In other words, he is saying that if you give too much, people will come to expect it of you, and eventually you will come to the point where you have nothing left to give. People will take all they can. If you are too generous, the people will take advantage of you. Now, there is not much to show whether or not Machiavelli was a generous man, except for his upbringing. His father was the poorest member of his family, a "doctor of laws" (Encyclopaedia Britannica 1) who "lived frugally" (Encyclopaedia Britannica 1). He could not afford the best teachers for Machiavelli, so they did what they could with the little money that they had. With this fact alone, Machiavelli more than likely gave what he could to the public, for he knew what it was like not having very much. What he gave was not very much, though, because he knew whatever he did give, he would not have for a situation when he might need it. And to wait for someone else to be generous towards him was, simply, not in his personality.
One chapter from The Prince is entitled "On Cruelty and Mercy and Whether It Is Better to Be Loved Than to Be Feared or the Contrary".