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This article presents a close reading of Ibn ʿAsākir’s (d. 571/1176) biography of ʿUmar II in the Tārīkh madīnat Dimashq. Although there was an earlier and substantial historiographical tradition, Ibn ʿAsākir’s biography is distinct from those of his predecessors in two major ways. First, he strategically arranged his biography to emphasize or de-emphasize certain aspects of ʿUmar II’s life, including his youth, rise to the caliphate, and reputation as a redeemer. Second, Ibn ʿAsākir’s legitimizing historiography appears to be bi-directional. Namely, where earlier biographers depicted ʿUmar II as the “fifth of the Rāshidūn,” bolstering the later Umayyad’s reputation through an association with earlier authorities, in Ibn ʿAsākir’s account problematic aspects of the early civil wars and fitna-ridden Rāshidūn period are also elided through the Rāshidūn’s association with the famously pious ʿUmar II. The context for this bi-directionality is to be found in the political and social environment in which Ibn ʿAsākir compiled his Tārīkh, where dual pressure from Crusader and Shiʿite opponents contributed to his articulation of a particular Sunni vision of political and religious continuity that relied heavily on ‘Umar II’s unique persona.