In 839/40 the horseman caused the emperor Theophilos (829–42) and the residents of Constantinople tremendous concern by dropping its gilded toupha, the plumed helmet-crown. The horseman’s behavior was interpreted as an ominous, foreboding action. Theophilos had repeatedly aligned himself with the horseman in his triumphs of 831 and 837 by wearing a toupha, and a toupha also makes an unprecedented appearance on Theophilos’ copper coins. The golden toupha encapsulated the splendors of triumphal rulership and interlinked Theophilos with Justinian. The bronze horseman had become the symbol of victory and a testament to the return of Byzantine martial prowess. The horseman dropped the toupha in the aftermath of Theophilos’ humiliating defeat by the Abbasids in 838. An urgent and ingenious restoration is narrated in the chronicle of Symeon the Logothete. While previous scholarship has recognized Theophilos’ architectural competition with the Abbasids, the horseman has not been included in analyses of cross-cultural dialogue. This chapter argues that Justinian’s horseman came to symbolize the city and serve as a harbinger of the imperial future. The bronze horseman's "actions" were interpreted in Constantinople as divinatory indications of the future of the Byzantine–Abbasid rivalry.