This paper traces the deeds and evolving images of Liu Mengyan (1219–ca.1295), the top candidate in the 1244 civil service examination who was later promoted to Chief Councilor of the Southern Song (1127–1279) in 1275. After the Southern Song collapse, Liu joined the Yuan (1271–1368) government and continued his career as a high official. In contrast to the prominent Song loyalist Wen Tianxiang (1236–83), who enjoyed excellent posthumous fame, Liu Mengyan was repeatedly denounced upon his death and even became an icon of disloyalty. This paper examines how this image of disloyalty was forged from the late-thirteenth century onwards. It suggests that the way Liu’s contemporaries and later literati interpreted and portrayed his deeds depended on political and social circumstances, and this in turn related to the ideal loyalist prototype by which they considered Liu, as well as on their interpretation of the concept of loyalty and their attitudes towards non-Han “barbarians.”