Machiavelli on Conspiracy

The Longest Chapter in the Discourses

Book III, Chapter 6 of the Discourses on Livy is Machiavelli's treatise on conspiracy — and it is, by a wide margin, the longest chapter in the entire work. This tells us something about what Machiavelli considered important. Conspiracy was not a marginal topic for him; it was the mechanism by which political orders were overthrown, reformed, or destroyed. Understanding conspiracy was therefore essential for both princes who wished to survive and republicans who wished to protect liberty.

Machiavelli's approach was characteristically empirical. He collected dozens of historical examples — from ancient Rome, from Greek history, from contemporary Italian politics — and analyzed them systematically to determine why most conspiracies fail and what distinguishes the rare successes. His conclusion was sobering: conspiracy is the most dangerous enterprise in politics, and the odds are overwhelmingly stacked against the conspirators.

Three Phases of Failure

Machiavelli identified three phases where conspiracies break down. The first is planning: the more people who know about a conspiracy, the more likely it is to be betrayed. Every additional conspirator is a potential traitor, and the longer the planning takes, the more opportunities there are for discovery. One participant's change of heart, one careless remark, one intercepted letter — and the conspiracy is exposed.

The second phase is execution: even well-planned conspiracies fail at the moment of action. Conspirators lose their nerve, the target changes his routine, weapons malfunction, and the chaos of the moment produces errors that cannot be recovered. Machiavelli noted that assassinations are especially prone to failure because they require precision in a situation that is inherently chaotic.

The third phase is aftermath: even a successful assassination or coup often fails to achieve its political objectives. The conspirators may kill the prince but face his allies, his army, or a populace loyal to the old order. Machiavelli cited the assassination of Julius Caesar as the paradigm case: Brutus and Cassius succeeded in killing Caesar but failed to restore the Republic because the political conditions that had made Caesar's rise possible still existed.