Chapter 20
Why Fortresses Are Usually a Trap—And Where Real Security Actually Comes From
ARE FORTRESSES, AND MANY OTHER THINGS TO WHICH PRINCES OFTEN RESORT, ADVANTAGEOUS OR HURTFUL? 1. Some princes, so as to hold securely the state, have disarmed their subjects; others have kept their subject towns distracted by factions; others have fostered enmities against themselves; others have laid themselves out to gain over those whom they distrusted in the beginning of their governments; some have built fortresses; some have overthrown and destroyed them. And although one cannot give a final judgment on all of these things unless one possesses the particulars of those states in which a decision has to be made,…
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Key Quotes & Analysis
"There never was a new prince who has disarmed his subjects; rather when he has found them disarmed he has always armed them, because, by arming them, those arms become yours, those men who were distrusted become faithful, and those who were faithful are kept so, and your subjects become your adherents."
Context: Arming versus disarming subjects
Security through shared arms beats security through stripping the people of weapons.
In Today's Words:
Machiavelli distrusts factions inside your own base. Venice kept noble parties divided and still paid for it when outside pressure arrived. Splitting your organization so you can control it may work briefly, but it leaves you weak when a stronger force enters. Unity you manufacture through division is not the same as loyalty.
"I do not believe that factions can ever be of use; rather it is certain that when the enemy comes upon you in divided cities you are quickly lost, because the weakest party will always assist the outside forces and the other will not be able to resist."
Context: Venice and divided cities
Internal division is an invitation to outside force.
In Today's Words:
Fortune often sends enemies so a new prince can climb by defeating them. Opposition can become the stage on which you earn reputation. In a campaign or turnaround, the crisis everyone feared may be the exact moment that lets a decisive leader prove they are not merely occupying the title.
"Without doubt princes become great when they overcome the difficulties and obstacles by which they are confronted, and therefore fortune, especially when she desires to make a new prince great, who has a greater necessity to earn renown than an hereditary one, causes enemies to arise and form designs against him, in order that he may have the opportunity of overcoming them, and by them to mount higher, as by a ladder which his enemies have raised."
Context: Enemies as a ladder
Opposition can become the stage on which a new prince earns reputation.
In Today's Words:
The best fortress is not to be hated by the people. Walls fail when the crowd opens the gate for an outsider. Popular goodwill protects more than stone because hatred defeats every barrier once the base decides your removal is their gain. Security starts with what people feel, not what you build.
"For this reason the best possible fortress is—not to be hated by the people, because, although you may hold the fortresses, yet they will not save you if the people hate you, for there will never be wanting foreigners to assist a people who have taken arms against you."
Context: Popular goodwill versus walls
Hatred defeats stone; outside powers will help a risen populace.
In Today's Words:
The best fortress is not to be hated by the people. Walls fail when the crowd opens the gate for an outsider. Popular goodwill protects more than stone because hatred defeats every barrier once the base decides your removal is their gain. Security starts with what people feel, not what you build.
Thematic Threads
Tools of Control
In This Chapter
Machiavelli explores whether fortresses and constraints help or hurt
Development
This theme connects to the broader analysis of power throughout the work
In Your Life:
Consider how security vs trust, defensive measures, control structures 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 say fortresses are often useless or harmful to a prince?
analysis • mediumOne way to read it
They can create false confidence and cannot substitute for popular goodwill or loyal arms. In some cases they provoke hatred by showing distrust, and in others they fail when the people outside the walls turn against you or invite enemies in.
- 2
When can fortresses help, and when do they create false confidence?
analysis • mediumOne way to read it
They may aid a prince who fears his people more than foreigners, or hurt one who is hated by the people and trusted abroad. Machiavelli refuses one answer for all states: fortresses matter only relative to where your real danger lies.
- 3
Why does Machiavelli recommend arming your subjects rather than disarming them, and what does he recommend instead of walls for winning security?
analysis • deepOne way to read it
Arming loyal subjects turns them into adherents; disarming them breeds hatred and forces reliance on mercenaries. Real security comes from the people's goodwill, well-used arms, and wise governance, not from fortifications alone.
- 4
Where have you seen a leader rely on legal barriers or title protection while losing the people's goodwill?
application • mediumOne way to read it
Executives hiding behind contracts, politicians trusting incumbency, or managers citing policy while morale collapses repeat the fortress mistake: structural protection without loyal support fails when pressure arrives.
- 5
Are Machiavelli's anti-fortress arguments still relevant in an age of media and institutional trust?
reflection • deepOne way to read it
Yes, if fortresses mean any defensive shell that substitutes for loyalty: legal armor, brand prestige, or procedural delay. His point is that no barrier holds when those inside or outside no longer accept your rule.
Critical Thinking Exercise
Applying Tools of Control
Analyze a current challenge in your professional life through the lens of whether fortresses and constraints help or hurt.
Consider:
- •How does tools of control affect your situation?
- •What strategic options does understanding security vs trust, defensive measures, control structures reveal?
Journaling Prompt
How might a deeper understanding of security vs trust, defensive measures, control structures change your approach to leadership?
Coming Up Next...
Chapter 21: How to Build a Reputation That Makes Enemies Recalculate Before Acting
In the next chapter, Machiavelli turns to another crucial aspect of power and leadership...
