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| Foreword | |
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| Dedication: to His Magnificence Lorenzo de' Medici./Of Patrons and Proteges | |
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| Concerning New Principalities Acquired by One's Own Forces and Personal Ability./Starting a Business | |
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| Why The Kingdom of Darius, Conquered by Alexander, did not Rebel against his Successors after Alexander's Death./Business and Government | |
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| On New Principalities Acquired with the Forces and Fortune of Others./Inherited Business | |
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| On Hereditary Principalities./Family Business | |
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| The Classification of Principalities and How they are Acquired./Capturing a Company | |
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| On Mixed Principalities./Controlling a Captured Company | |
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| How Cities and Principalities, which Prior to Occupation were Accustomed to Living under their Own Laws, Should be Administered./The Running of a Recently Acquired Business | |
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| On Those who Acquire Principalities through Wicked Deeds./Stealing a Business | |
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| On Civil Principalities./ Rising to Power | |
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| On the Different Types of Army and the Question of Mercenary Troops./ The use of Consultants | |
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| On Auxiliary Troops, your own Troops, and a Mixture of the Two./ The need for Loyalty | |
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| On Cruelty and Mercy: and Whether it is Better to be Loved than Feared, or the Reverse./ Managing People | |
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| On the Secretaries Who Accompany the Prince./ The Power of the Employee | |
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| On Ecclesiastical Principalities./ Dealing with the Establishment | |
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| How a Prince Should Act Concerning Military Affairs./ The need for Total Dedication | |
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| Whether Princes Should Keep Their Word./ The use of Craftiness | |
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| How the Strength of Every Principality Should be Measured./ Finance and the Understanding of Money | |
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| On Generosity and Meanness./ Controlling Expenditure | |
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| How Flatterers are Avoided./ Flattery and False Profits | |
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| Whether Fortresses and Many Other Things Commonly Used by Princes are Useful or Useless./ Structuring the Business | |
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| On the Things for which Men, and especially Princes, are Praised or Blamed./ The Company Image | |
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| On the Avoidance of Contempt and Hatred./ Public Relations | |
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| How a Prince Should Act in Order to Gain Reputation./ The Advantages and Dangers of Fame | |
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| Why the Princes of Italy have Lost their States./ Why Businesses Fail | |
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| How Much Fortune can Influence Human Affairs, and How She Should be Resisted./ Creating one's own Luck | |