The only surviving Byzantine image of the horseman inhabits an ominous and foreboding landscape. The unique image appears in an illustrated version of the Book of Job. The horseman presides over a darkly emotional and philosophically rich scene (Vat. Gr. 751, fol. 26r). The artist who created this image transported the horseman back in time to have it preside over the darkest moment in the trials of virtuous Job caught up in a contest between forces far greater than himself. Given that the motif of fall permeates the Book of Job, our image metaphorically envisions a bitter estrangement from the Queen of Cities. In this unique image of Job, Justinian’s column is multivalent. It is both triumphal and tragic. If it were not juxtaposed with Job’s suffering it would seem celebratory. However, the juxtaposition is central. The horseman is poised to witness how the righteous suffer as a result of a cosmic battle between good and evil. Either the manuscript’s creator was very prescient in forecasting Job-like tribulations for Constantinople or he was operating with hindsight at some point after the Crusader capture of Constantinople in 1204.