Reading Pointers for Sharper Insight

To understand the points Machiavelli makes in The Prince, pay attention to the following:

Machiavelli's Time and the Politics of Italy:

During Machiavelli's time, Italy was broken into five separate entities, which created five political powers; however, the Medici family ruled Florence and Machiavelli curried favor with them. It was obvious to him that politics had its own rules, and it was unnecessary to subjugate them to any other set of rules.

Machiavelli arranged his novel so it would proceed from general information and advice to specific areas of major relevance to the Medici family.

Fate as Opposed to Free Will:

According to Machiavelli, Fate or Fortune (events that are beyond human control) affects the major portion of life and Free Will (man's decisions, actions, etc.), controls the rest. He states that princes can prepare themselves for the vagaries of Fortune by having the willingness to change their ways quickly to accommodate whatever Fortune brings. Therefore, cautious rulers are frowned upon, and careless rulers are praised the former believe they have the ability to control fate to some degree.
Good will and Deception:

Machiavelli encourages leaders to rule using deceit. By telling the people what they want or expect to hear, which is not always the truth, a prince will be a stronger, more powerful leader. Lying and breaking promises is a necessary part of being a prince; however, when promises must be broken, a plausible lie will be easy for the people to accept.
War and Peace:

Being an effective war leader is imperative to being a successful ruler. A prince's sole priority is to keep the people content and happy, which, in turn, will make them loyal and supportive subjects and more ready to support the ruler in times of war.
Moral and immoral behavior:

The qualities by which a ruler must govern are not restricted by the philosophical considerations of right and wrong. Princes must maintain their positions, regardless of changing situations.