This chapter discusses Arrian’s characterization of Alexander the Great. Beginning from a brief history of scholarship on Arrian and his unusually large role in shaping modern understandings of Alexander, it approaches Arrian as an active creator of historical knowledge. Using examples from the Anabasis, it demonstrates that Arrian observed a shift in Alexander’s behaviour arising from the increasingly complex political and personal circumstances of his life. He described this change overtly at times, but more often by setting Alexander into a literary framework based on Herodotus’ portraits of despotic Persian kings and tweaked to reflect philosophical and moral concerns contemporary in Arrian’s own lifetime. The Anabasis forms the core of the discussion but the Discourses of Epictetus and the Indica provide complementary readings and show consistency in Arrian’s approach to his favourite subject.