Chapter 19
The One Thing That Destroys Every Leader: How to Never Be Hated or Despised
THAT ONE SHOULD AVOID BEING DESPISED AND HATED Now, concerning the characteristics of which mention is made above, I have spoken of the more important ones, the others I wish to discuss briefly under this generality, that the prince must consider, as has been in part said before, how to avoid those things which will make him hated or contemptible; and as often as he shall have succeeded he will have fulfilled his part, and he need not fear any danger in other reproaches. It makes him hated above all things, as I have said, to be rapacious, and to…
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Key Quotes & Analysis
"It makes him hated above all things, as I have said, to be rapacious, and to be a violator of the property and women of his subjects, from both of which he must abstain. And when neither their property nor their honor is touched, the majority of men live content, and he has only to contend with the ambition of a few, whom he can curb with ease in many ways."
Context: What breeds hatred
The fastest path to hatred is taking what people hold most dear: wealth and honor.
In Today's Words:
Conspiracies need a public payoff. If removing you would anger the people, most plots die in planning. Machiavelli treats popular goodwill as practical security, not sentiment. Leaders who protect the base from confiscation, contempt, and elite predation sleep better than leaders who trust walls, titles, or secret police alone.
"princes ought to leave affairs of reproach to the management of others, and keep those of grace in their own hands. And further, I consider that a prince ought to cherish the nobles, but not so as to make himself hated by the people."
Context: France and the division of reproach
Institutions can absorb blame while the prince keeps the credit.
In Today's Words:
Institutions can absorb blame while the prince keeps credit. France divided unpopular work among ministers and magistrates so the crown looked cleaner. Do not take every unpopular hit in your own name if the structure allows a legitimate agent to carry reproach, but make sure the base does not connect you to the harm.
"Therefore a prince, new to the principality, cannot imitate the actions of Marcus, nor, again, is it necessary to follow those of Severus, but he ought to take from Severus those parts which are necessary to found his state, and from Marcus those which are proper and glorious to keep a state that may already be stable and firm."
Context: Closing lesson from the emperors
Founding and preserving require different models; imitation must match your situation.
In Today's Words:
New rulers cannot imitate old emperors wholesale. Founding requires Severus's tools. Preserving requires Marcus's virtues. Copy the wrong model for your moment and you fail twice: too soft to secure power or too harsh to keep it. Match the playbook to whether you are building the state or stabilizing what already exists.
"one of the most efficacious remedies that a prince can have against conspiracies is not to be hated and despised by the people, for he who conspires against a prince always expects to please them by his removal; but when the conspirator can only look forward to offending them, he will not have the courage to take such a course, for the difficulties that confront a conspirator are infinite."
Context: Conspiracy and popular goodwill
Conspiracy needs a public payoff; remove that payoff and the plot loses nerve.
In Today's Words:
Conspiracies need a public payoff. If removing you would anger the people, most plots die in planning. Machiavelli treats popular goodwill as practical security, not sentiment. Leaders who protect the base from confiscation, contempt, and elite predation sleep better than leaders who trust walls, titles, or secret police alone.
Thematic Threads
Avoiding Contempt
In This Chapter
Machiavelli explores how to avoid being hated or disrespected
Development
This theme connects to the broader analysis of power throughout the work
In Your Life:
Consider how dignity, consistency, protecting your reputation appear in your own professional environment
You now have the context. Time to form your own thoughts.
Discussion Questions
This is not a test. Five prompts guide you through the chapter, from how it opens to how it closes, so you notice context and rhythm rather than facts to memorize. Sit with each question in your own words. When you see "One way to read it," treat it as a starting point, not the only answer.
- 1
Why does Machiavelli treat hatred and contempt as more dangerous to a prince than being feared?
analysis • mediumOne way to read it
Fear can secure obedience if it does not become hatred. Hatred and contempt remove even that restraint and make conspiracy likely. A prince who is despised or widely hated loses internal security no matter how well armed he appears.
- 2
How should a prince handle property, women, and the honors of his subjects to avoid becoming hated?
analysis • mediumOne way to read it
He must abstain from rapacity and from violating subjects' property and women. When honor and possessions are untouched, most men live content and only a few ambitious rivals need curbing. Theft and humiliation turn fear into active hatred.
- 3
What does Machiavelli say is the most efficacious remedy a prince can have against conspiracies?
analysis • deepOne way to read it
Not to be hated or despised by the people. Conspirators expect the public to welcome the prince's removal; if their plot would only offend the people, they lose courage. Conspiracy is hard to execute, easy to expose, and nearly impossible when the base remains loyal.
- 4
When have you seen a leader destroyed not by enemies but by widespread contempt from the people they ruled?
application • mediumOne way to read it
Leaders seen as fickle, weak, or mean-spirited invite mockery before rebellion. Machiavelli warns that contempt makes conspiracy attractive and defense difficult even when formal power still looks intact.
- 5
Is avoiding hatred a moral rule in Machiavelli, or simply a survival rule?
reflection • deepOne way to read it
Primarily survival. He does not forbid all harshness, but he treats abstaining from plunder and insult as politically necessary. Avoiding hatred is the line where fear remains usable instead of becoming a death sentence.
Critical Thinking Exercise
Applying Avoiding Contempt
Analyze a current challenge in your professional life through the lens of how to avoid being hated or disrespected.
Consider:
- •How does avoiding contempt affect your situation?
- •What strategic options does understanding dignity, consistency, protecting your reputation reveal?
Journaling Prompt
How might a deeper understanding of dignity, consistency, protecting your reputation change your approach to leadership?
Coming Up Next...
Chapter 20: Why Fortresses Are Usually a Trap—And Where Real Security Actually Comes From
In the next chapter, Machiavelli turns to another crucial aspect of power and leadership...
