Sulla and Caesar are linked in Roman history by their willingness to invade Italy, their victories in civil wars, and their assumption of dictatorships. Their military successes provided them the means to seize sole power for themselves. How, then, are we to judge those victories? How does military success interact with a statesman’s moral character and political achievement, particularly when military victories enable tyranny? Plutarch’s Sulla and Caesar are surprisingly silent about these questions. This chapter builds on previous scholarship to explore the nature of this silence. One reason to read these two biographies together is that both share a similar fundamental structure: a controversial political rise (Sull. 1–10; Caes. 1–14) and an autocratic political finish (Sull. 30–38; Caes. 57–69) that bookend an extended narrative of military victories in foreign and then civil wars (Sull. 11–29; Caes. 15–56). The political narratives of these two Lives emphasize vices and weaknesses in the characters of their subjects while the military narratives display their virtues and victories, thus establishing a tension between the two spheres that Plutarch chooses not to resolve (Sull. 30.6; Caes. 69.1). The chapter concludes by considering whether Plutarch’s respect for military success is perhaps too ingrained for him to fault it for the political consequences it makes possible.