I say that every prince must desire to be considered merciful and not cruel. He must, however, take care not to misuse this mercifulness.

A prince, therefore, must not mind incurring the charge of cruelty for the purpose of keeping his subjects united and confident; for, with a very few examples, he will be more merciful than those who, from excess of tenderness, allow disorders to arise, from whence spring murders and rapine; for these as a rule injure the whole community, while the executions carried out by the prince injure only one individual. And of all princes, it is impossible for a new prince to escape the name of cruel, new states being always full of dangers.

...it behooves us to adapt oneself to the times if one wants to enjoy continued good fortune.

Any harm you do to a man should be done in such a way that you need not fear his revenge.

To know in war how to recognize an opportunity and seize it is better than anything else.

The first method for estimating the intelligence of a ruler is to look at the men he has around him.

And the prince who has relied solely on their words, without making other preparations, is ruined, for the friendship which is gained by purchase and not through grandeur and nobility of spirit is merited but is not secured, and at times is not to be had.