By William R. Cook, Ph.D., State University of New York at Geneseo
One of the questions we might ask Machiavelli is how important is glory as opposed to power? How do we deal with the fact that some leaders that kill a lot of people end up being successful?

Niccolò Machiavelli deals with this very question in one of the most famous passages in The Prince. He says:
Many others … employing cruel means were unable to hold on to their state even in peaceful times, not to speak of the uncertain times of war. I believe this depends on whether cruelty be badly or well used. Those cruelties are well used, if it is permitted to speak well of evil, that are carried out in a single stroke, done out of necessity to protect oneself and then are not continued, but are instead converted into the greatest possible benefits for the subjects. Those cruelties are badly used that, although few at the outset, increase with the passing of time, instead of disappearing. Those who follow the first method can remedy their standing both with God and with men, as Agathocles did. The others cannot possibly maintain their position.
We want to put cruelty and well used in separate categories and make them exclusive of one and another, but Machiavelli says cruelty can be well or ill used.
This is language that is particularly disturbing to a lot of people: “cruelty well used.” We want to put cruelty and well used in separate categories and make them exclusive of one and another, but Machiavelli says cruelty can be well or ill-used. The very language shocks us, and Machiavelli knows it shocks us. This would have been nonsense to Aristotle and to Cicero—these two great venerated classical authors and thinkers whose political ideas have so penetrated the culture of Western Europe, even more so during the Renaissance. Yet Machiavelli talks about well-used cruelty. It reminds us that this was a different kind of book, in some ways, than has ever been written in the West.
This is a transcript from the video series Machiavelli in Context. Watch it now, on The Great Courses.
It is a difficult task, but we need to appreciate how staggeringly different this is. Today, as well as in Machiavelli’s time, how people respond to phrases like “well-used cruelty.” You just did something cruel: Well done in this case, or badly done—either way.
Today, we find books, like Machiavelli’s Virtue, which argues for a need to understand Machiavelli as a political thinker who has described realities that need to be taken seriously. Leo Strauss, the famous 20th-century political thinker, referred to Machiavelli as a “teacher of evil.”
One of the great questions surrounding Machiavelli’s teachings is, is there a new political morality, political amorality, or political immorality being justified? The answer isn’t a simple one. But it does provide the opportunity to consider the notion of what Machiavelli says to develop your thinking about this topic, explore it, relate it to other things, and craft your own answer.
That’s what’s important—not a determined opinion held by someone else, but the opportunity to empower everyone to think a little bit differently, to wonder whether the categories, the boxes that we create, are the only possible boxes or are the best boxes in which to put things. When we hear a phrase like “well-used cruelty,” it reminds us that Machiavelli is, to use an over-used phrase, thinking outside the box, or, we might say, a new paradigm of political thought and political behavior.
Learn more about Machiavelli’s philosophy of circumstances, fortuna, and his recipe for military action, virtue
Agathocles of Syracuse
Is Syracuse, where Agathocles ruled, a more stable, a more ordered, and a more secure place? And if that is so, isn’t that cruelty well used?

The example that Machiavelli gives is one of those that his audience was more familiar with than today’s readers unless we’re very familiar with classical history—a guy named Agathocles of Syracuse. Agathocles is an example of somebody who used cruelty well, did it early, all at once, and got on with things. Machiavelli says both people and God will forgive that kind of cruelty. We have to ask, “What did it lead to? What did it permit or make more likely to happen?” Is Syracuse, where Agathocles ruled, a more stable, more ordered, and more secure place? If that is so, isn’t that cruelty well used, Machiavelli asks? Or, do we simply say cruelty is always unjust and leads to bad consequences. That’s certainly what Cicero would say. Therefore, once we hear cruelty, we already know where to classify this man—bad guy, tyrant, or whatever label we want to put on it.
Learn more: Machiavelli’s The Art of War
The Challenge of Machiavelli
Machiavelli is challenging. He was challenging in his own time. He was challenged, of course, the ideas of Cicero and Aristotle, and also the traditional Christian morality. He was challenged what’s being passed down as the word of God through interpretations of scripture, through ways that people read what Jesus said, and trying to find the political implications. Jesus didn’t talk very openly and directly about politics, but Jesus certainly gave moral lessons that many people believe are meant to apply in the macrocosm, as well as the microcosm of the individual person.
Learn more about the historical Jesus
If what you’re trying to achieve is a certain vision of a society and you aren’t there yet, the question is how do you get there? What’s legitimate to get there?
Machiavelli still challenges all that. One of the ways he challenges it is in saying: If what you’re trying to achieve is a certain vision of society and you aren’t there yet, how do you get there? What’s legitimate to get there? These are tougher questions than we might have thought. To understand, we need to look from a variety of perspectives. We may decide, as Leo Strauss did, that Machiavelli is simply a teacher of evil. Or we might decide something very different. But a passage like the one above is one that does indeed stimulate us to think and ask whether our boxes, our labels, and our paradigms are the only ones there can be.
Common Questions About Machiavelli and Cruelty
For Machiavelli, certain situations, such as war, call for the use of cruelty. He believes that cruelty is sometimes necessary to be perceived as a strong leader and to protect one’s people.
According to Machiavelli, if a prince is too merciful, then others will view him as weak. Being merciful to a few can actually cost more lives in the long run because it leaves the country that the prince rules over vulnerable to attacks.
Q: Why is fear stronger than love, according to Machiavelli?
Although Machiavelli believed that ideally, one would be both feared and loved, if given the choice, it is better to be feared. If a prince is not feared, he is likely to be assassinated or leave his country open for invasions.
In general, Machiavelli held a pessimistic view of human nature. He believed that most men were not to be trusted and would betray you if given the chance, so as a leader, it is important to be cunning and inspire fear in others. In this sense, men are loyal to you because they fear the consequences of double-crossing you.