In this chapter, Machiavelli’s complex intellectual identity is encapsulated in the signature “historian, comic writer, and tragic writer”, found in his 1525 letter to Guicciardini. This unusual self-designation reveals his multifaceted role as a writer—ranging from historian to dramatist—and signifies his efforts to establish his intellectual reputation. Machiavelli’s exploration of history combines detailed observation with a deep understanding of political causality, revealing an approach more akin to archaeology. His work reflects his commitment to preserving historical memory through precise narration. This chapter also addresses the tension between history and poetry, recognizing their shared cognitive potential. The chapter reveals Machiavelli’s identity as a writer dedicated to probing both the details of historical events and the broader human experience through multiple literary forms.