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Why Mercenaries Will Betray You at the Worst Possible Moment — The Prince

The Prince - Why Mercenaries Will Betray You at the Worst Possible Moment

Niccolò Machiavelli

The Prince

Why Mercenaries Will Betray You at the Worst Possible Moment

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Analysis by the Wide Reads editorial team·Reviewed against the source text·Updated November 29, 2025

Summary

Why Mercenaries Will Betray You at the Worst Possible Moment

The Prince by Niccolò Machiavelli

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Machiavelli turns from how principalities are acquired and held to how they are defended. Good laws require good arms, and a prince's arms are either his own, mercenary, auxiliary, or mixed. Mercenaries and auxiliaries are useless and dangerous: disunited, ambitious, undisciplined, brave among friends and cowardly before enemies. In peace they rob you; in war the enemy defeats you because they will not die for a stipend.

Italy's ruin proves the point. For years her princes rested on mercenaries who looked formidable until Charles VIII seized the peninsula with chalk in hand. Machiavelli says the real sin was princely reliance on hired arms, and princes paid the penalty.

Mercenary captains create a double trap. If they are able, they aspire to their own greatness and may oppress you or pursue goals against your interest. If they are unable, you are ruined in the ordinary way. Machiavelli answers critics by insisting that princes should command in person and republics should send citizens, recalling failures and binding successes by law. Rome, Sparta, and the Swiss stayed armed and free.

History fills the chapter with warnings: Carthage oppressed by mercenaries; Philip of Macedon taking Theban liberty; Francesco Sforza beating the Venetians at Caravaggio then crushing Milan, his employers; Pagolo Vitelli showing Florence that a victorious captain becomes master whether you obey or resist. Venice prospered at sea with its own men, then on land hired Carmignuola, murdered him when he grew too strong and lukewarm, and later lost at Vaila in one battle what eight hundred years had built.

Machiavelli traces Italy's mercenary habit to Church and republics unaccustomed to arms after the empire's fall. From Alberigo da Conio's school came captains like Braccio and Sforza who debased infantry, inflated cavalry, and wrote rules to avoid fatigue and danger until Charles, Louis, Ferdinand, and the Swiss reduced Italy to slavery and contempt.

In this chapter: Terms Characters Key Quotes Themes Modern Story

Why This Matters

Connect literature to life

Skill: Owning Your Core Force

Machiavelli argues that mercenary and auxiliary arms are useless and dangerous because they fight for stipend, not death, and because able captains aspire to their own greatness while unable ones lose wars. He traces Italy's collapse under Charles VIII, Francesco Sforza's betrayal after Caravaggio, Venice's murder of Carmignuola and loss at Vaila, and the mercenary rules that avoided real fighting until foreign powers reduced the country to slavery and contempt. Not to outsource the force your state depends on, and to command your own people under laws you control before a competent hired operator becomes your master or an incompetent one loses everything.

Coming Up in Chapter 13

In the next chapter, Machiavelli turns to another crucial aspect of power and leadership...

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Original text
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Chapter 12

Why Mercenaries Will Betray You at the Worst Possible Moment

HOW MANY KINDS OF SOLDIERY THERE ARE, AND CONCERNING MERCENARIES Having discoursed particularly on the characteristics of such principalities as in the beginning I proposed to discuss, and having considered in some degree the causes of there being good or bad, and having shown the methods by which many have sought to acquire them and to hold them, it now remains for me to discuss generally the means of offence and defence which belong to each of them. We have seen above how necessary it is for a prince to have his foundations well laid, otherwise it follows of necessity…

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Key Quotes & Analysis

"Mercenaries and auxiliaries are useless and dangerous; and if one holds his state based on these arms, he will stand neither firm nor safe; for they are disunited, ambitious, and without discipline, unfaithful, valiant before friends, cowardly before enemies; they have neither the fear of God nor fidelity to men, and destruction is deferred only so long as the attack is; for in peace one is robbed by them, and in war by the enemy."

— Machiavelli

Context: Opening verdict on hired arms

Machiavelli states the thesis before the historical proof: mercenary arms fail in both peace and war.

In Today's Words:

Mercenary captains create an impossible choice. If they are competent, they may become your rival. If they are incompetent, they lose your wars. Venice tried murdering Carmignuola when he grew too strong and still lost at Vaila under later hired captains. Outsourced force protects its own billing model, not your mission.

"Thus it was that Charles, King of France, was allowed to seize Italy with chalk in hand;[1] and he who told us that our sins were the cause of it told the truth, but they were not the sins he imagined, but those which I have related. And as they were the sins of princes, it is the princes who have also suffered the penalty."

— Machiavelli

Context: Italy's mercenary collapse

Foreign conquest was the price of princely dependence on soldiers who would not fight.

In Today's Words:

Charles VIII took Italy easily because princes hired armies that would not die for them. That is the mercenary trap in one line. If the people holding the swords do not share your stake in the outcome, your state is already conquered in principle and only waiting for the first foreign march.

"The mercenary captains are either capable men or they are not; if they are, you cannot trust them, because they always aspire to their own greatness, either by oppressing you, who are their master, or others contrary to your intentions; but if the captain is not skilful, you are ruined in the usual way."

— Machiavelli

Context: The captain's double trap

Competence creates ambition; incompetence creates defeat. There is no safe mercenary middle.

In Today's Words:

Italian mercenaries rewrote war to avoid real danger until the country could not defend itself. They inflated cavalry, degraded infantry, and formalized fake fighting. When leaders outsource the core job to people paid to minimize risk, the system looks active while leaving you helpless the moment a serious enemy arrives.

"They had, besides this, used every art to lessen fatigue and danger to themselves and their soldiers, not killing in the fray, but taking prisoners and liberating without ransom. They did not attack towns at night, nor did the garrisons of the towns attack encampments at night; they did not surround the camp either with stockade or ditch, nor did they campaign in the winter. All these things were permitted by their military rules, and devised by them to avoid, as I have said, both fatigue and dangers; thus they have brought Italy to slavery and contempt."

— Machiavelli

Context: How Italian mercenaries debased war

Mercenary incentives produced a fake war that looked active but left Italy helpless.

In Today's Words:

Italian mercenaries rewrote war to avoid real danger until the country could not defend itself. They inflated cavalry, degraded infantry, and formalized fake fighting. When leaders outsource the core job to people paid to minimize risk, the system looks active while leaving you helpless the moment a serious enemy arrives.

Thematic Threads

The Danger of Hired Help

In This Chapter

Machiavelli explores why relying on contractors and mercenaries fails

Development

This theme connects to the broader analysis of power throughout the work

In Your Life:

Consider how in-house vs outsourced, loyalty, skin in the game 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. 1

    Why does Machiavelli call mercenary arms useless and dangerous for a prince?

    ▶One way to read it

    Mercenaries fight for pay, not your cause. They are disunited, ambitious, undisciplined, brave before friends and cowardly before enemies, and they desert or bargain when war becomes real. In peace they rob you; in war they fail you.

    analysis • medium
  2. 2

    What examples from Italian history show mercenaries fighting cautiously, plundering friends, or switching sides?

    ▶One way to read it

    Sforza was hired by Milan and turned on his employers; Carmignuola beat Milan for Venice then was killed when Venice feared him; Italy fell to Charles VIII with chalk in hand because condottieri would not die for their paymasters. Machiavelli treats these as the direct cause of Italy's ruin.

    analysis • medium
  3. 3

    How do mercenary captains profit from prolonging war rather than ending it?

    ▶One way to read it

    Their income and status depend on continued employment. They lowered infantry, favored cavalry they could afford, avoided night attacks, sieges, winter campaigns, and killing in battle. War became a billing model, not a path to victory, which left Italy enslaved and contemptible.

    analysis • deep
  4. 4

    When have you seen outsourced talent protect its own billing model instead of the organization's mission?

    ▶One way to read it

    Consultants who extend timelines, vendors paid by scope rather than outcome, or contractors who avoid the hard decisions that would end their contract all mirror condottieri who kept wars inconclusive because peace threatened their stipend.

    application • medium
  5. 5

    Is there any situation where hired force is acceptable, or does Machiavelli forbid it absolutely?

    ▶One way to read it

    For a prince who wishes to hold power, he nearly forbids it. Mercenaries may look capable, but capable captains aspire to your throne and incompetent ones lose your state. The only secure arms are those bound to you as subjects or citizens.

    reflection • deep

Critical Thinking Exercise

10 minutes

Applying The Danger of Hired Help

Analyze a current challenge in your professional life through the lens of why relying on contractors and mercenaries fails.

Consider:

  • •How does the danger of hired help affect your situation?
  • •What strategic options does understanding in-house vs outsourced, loyalty, skin in the game reveal?

Journaling Prompt

How might a deeper understanding of in-house vs outsourced, loyalty, skin in the game change your approach to leadership?

Coming Up Next...

Chapter 13: The Danger of Borrowed Armies—And Why You Must Build Your Own

In the next chapter, Machiavelli turns to another crucial aspect of power and leadership...

Continue to Chapter 13
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  • Reading Power Dynamics in Any SituationExplore the key chapters in The Prince that teach you to see who actually holds power, how they maintain it, and what they

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