Chapter 24
Why Italian Leaders Lost Everything: The Exact Mistakes That Destroyed Them
WHY THE PRINCES OF ITALY HAVE LOST THEIR STATES The previous suggestions, carefully observed, will enable a new prince to appear well established, and render him at once more secure and fixed in the state than if he had been long seated there. For the actions of a new prince are more narrowly observed than those of an hereditary one, and when they are seen to be able they gain more men and bind far tighter than ancient blood; because men are attracted more by the present than by the past, and when they find the present good they enjoy…
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Key Quotes & Analysis
"men are attracted more by the present than by the past, and when they find the present good they enjoy it and seek no further; they will also make the utmost defence of a prince if he fails them not in other things."
Context: New princes and present performance
Loyalty follows current results, not ancient lineage.
In Today's Words:
People defend you when the present works, not because of your pedigree. Machiavelli says men are drawn more by what is happening now than by ancient lineage. Loyalty follows current performance. Inherited titles and old reputations fade quickly when taxes rise, security falls, and the prince cannot show present competence.
"there will be found in them, firstly, one common defect in regard to arms from the causes which have been discussed at length; in the next place, some one of them will be seen, either to have had the people hostile, or if he has had the people friendly, he has not known how to secure the nobles."
Context: Why Italian princes fell
Bad arms plus either popular hatred or noble mismanagement destroys states.
In Today's Words:
Italian princes fell for a common pattern: bad arms plus either popular hatred or noble mismanagement. Failed armies and mishandled elites cost them their states. Machiavelli is diagnosing sloth, not bad luck alone. When leaders outsource force and mishandle both base and barons, fortune gets blamed for what negligence made inevitable.
"Philip of Macedon, not the father of Alexander the Great, but he who was conquered by Titus Quintius, had not much territory compared to the greatness of the Romans and of Greece who attacked him, yet being a warlike man who knew how to attract the people and secure the nobles, he sustained the war against his enemies for many years, and if in the end he lost the dominion of some cities, nevertheless he retained the kingdom."
Context: Counterexample of survival
Small power can endure when arms, people, and nobles are managed together.
In Today's Words:
Security that rests on your own strength is the only kind you can count on. Hoping a disgusted people will recall you is not a strategy. Machiavelli closes by insisting deliverance must be built, not wished for. If you lost power through dependence and neglect, recovery starts with arms and presence you control.
"those only are reliable, certain, and durable that depend on yourself and your valour."
Context: Closing deliverance
Hope of recall by a disgusted people is not a strategy.
In Today's Words:
Security that rests on your own strength is the only kind you can count on. Hoping a disgusted people will recall you is not a strategy. Machiavelli closes by insisting deliverance must be built, not wished for. If you lost power through dependence and neglect, recovery starts with arms and presence you control.
Thematic Threads
Why Leaders Fail
In This Chapter
Machiavelli explores common causes of leadership failure
Development
This theme connects to the broader analysis of power throughout the work
In Your Life:
Consider how complacency, external blame, taking responsibility 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
What common failings does Machiavelli identify among the Italian princes who lost their states?
analysis • mediumOne way to read it
Bad arms, as already discussed, plus either hostile people or friendly people mismanaged alongside disloyal nobles. Without those defects, a state strong enough to field an army should not be lost.
- 2
Why does he blame their sloth and bad arms more than fortune alone?
analysis • mediumOne way to read it
In quiet years they made no provision against change, a common human failing. When crisis came they thought of flight, not defense, and hoped the people would recall them after hating conquerors. That hope is a bad substitute for preparations that depend on yourself.
- 3
How did reliance on mercenaries and failure to win the people recur across these downfalls?
analysis • deepOne way to read it
Machiavelli ties Italy's lost states back to the arms question from earlier chapters: borrowed or mercenary force collapses under real pressure, and princes who neither secured nobles nor kept popular goodwill had no base when fortune turned.
- 4
Where have you seen leaders blame bad luck for outcomes their own neglect made likely?
application • mediumOne way to read it
Organizations that outsource core capability, ignore morale in good years, then call defeat unforeseeable repeat the Italian princes' pattern. Fortune changes; sloth leaves you with no answer when it does.
- 5
Does Machiavelli's diagnosis of Italy apply to any modern institution that outsources its core competence?
reflection • deepOne way to read it
Yes. When the essential function of power is rented out, the institution survives only while contractors find it profitable. Real security requires arms, laws, allies, and example that depend on your own valour, not on someone else's return.
Critical Thinking Exercise
Applying Why Leaders Fail
Analyze a current challenge in your professional life through the lens of common causes of leadership failure.
Consider:
- •How does why leaders fail affect your situation?
- •What strategic options does understanding complacency, external blame, taking responsibility reveal?
Journaling Prompt
How might a deeper understanding of complacency, external blame, taking responsibility change your approach to leadership?
Coming Up Next...
Chapter 25: Fortune Favors the Bold: How to Beat Bad Luck Before It Beats You
In the next chapter, Machiavelli turns to another crucial aspect of power and leadership...
