This chapter explores Machiavelli’s complex relationship with writing, presenting it as both a valuable tool and a potential risk. His correspondence and works reveal a clear tension between the intellectual freedom he finds in reading and the constraints imposed on his writing, especially under Medici rule. The chapter traces Machiavelli’s growing caution in navigating censorship and self-censorship while presenting a layered self-representation. He values oral exchanges over the written word, suggesting that writing—though powerful—can be a “rock” to guard against. In the Florentine Histories and his letters, Machiavelli embeds truths discreetly within carefully crafted texts, demonstrating his strategy of concealing insights through cautious disclosures. The chapter also tests Leo Strauss’s interpretation of Machiavellian thought.