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This paper engages a targeted comparison of the treatment and behavior of defeated generals in the Roman Republic and early Principate with equivalent cases evidence in Eastern Zhou and Han China (8th C. BCE to 3rd C. CE). Specifically, this paper explores three separate but related dynamics of defeat: how surviving defeated generals behave in defeat, how generals are remembered when they are killed in battle, and how they are treated by their leaders. Empires are forged in conquest, but no empire wins every battle, and all at some point have been confronted with the reality of their generals being defeated. Discourse around these defeated generals, however, is highly culturally specific. In a comparative study of defeated generals in Ancient Rome and Early China, these specific dynamics will be drawn out and illustrated. The topic of military authority in Rome is perennially studied by Classicists (Phang 2008; Drogula 2015; Armstrong 2017, to name just some recent examples), and the interplay of political structure and generalship in Rome has been extensively outlined already (Eckstein 1987). However, this paper approaches the matter in an innovative way: studies of defeat or surrender, rather than victory, are a much more recent phenomenon (de Libero 2012; Clark 2014; Clark and Turner 2018; Lentzsch 2019). Moreover, there has never been a directly comparative study of Roman generalship with its equivalents in the far east, despite efforts to compare state power of the two ancient empires (Scheidel 2009 and 2015, though one notes the cursory remarks on the matter of generals in Rosenstein 2009). By applying these lenses, both Roman and Chinese generals are highlighted as having a high “buy-in” to their societies, represented by their willingness to commit suicide on defeat or die in battle otherwise. However, the consequences faced for surviving a defeat were quite different. Roman generals could generally expect to be tried in court and fairly handled (as, for example, Gn. Papirius Carbo was after his defeat at Noreia in 113), but just as often could redeem themselves in later conflicts. Chinese generals seldom outlive a single defeat, and the practice of defection, seen in cases like that of Li Ling, is essentially unheard of in Rome. Moreover, the discourse around defeated generals is radically separated between the two cultures. The Roman state was in general more forgiving of its generals being defeated (failure was not a guaranteed death sentence), whereas when court astrologer Sima Qian even attempted to defend the defeated Li Ling, he was almost executed for defending the failure. A general trend around harsher penalties for failure for Chinese generals is evident in the comparison between Rome and China. When also considering the political evolution of Rome from a Republic to an Empire, and thus practices that gradually become more similar to Chinese equivalents, one sees in remaining differences the lingering vestiges of a Republican modality that continue to separate how two autocratic imperial states handle the failure of those tasked with military responsibilities.