The first paper considers ‘contraband’ portraits as a means to produce ambivalent symbols of emancipation, including several cartes de visite that acknowledge the subjectivity and individuality of their sitters while co-opting their likenesses for widely circulated, anti-slavery war propaganda. Such images raise questions of agency and self-possession that similarly vexed the fluid nature of freedom for African Americans in a wartime setting. The second paper affirms the ‘contraband’ figure as a continually resonant but complicated one by examining the representational challenges inherent in creating six commemorative ‘contraband’ statues at the Civil War Interpretive Center in Corinth. Preceding the controversy surrounding Confederate monuments, these statues offer a means to understand viable alternatives to engage public audiences with the Civil War through sculpture. Likewise, visual representations of battles, whether produced immediately or years after the engagement, demonstrate more about the creators themselves and the cultural context in which they produced the work, than they do about the lived experience of combat itself. The third paper will explore competing images of battles produced during the war by soldier-artists. While some soldiers propagated heroic depictions of combat (in line with popular wartime prints), others produced private reflections in their sketchbooks where they could explore the incompatibility of idealized depictions with the war’s inherent violence. Finally, the fourth paper examines naval veteran Xanthus Smith’s postbellum painting of a marine battle for the 1876 Centennial International Exhibition in Philadelphia. Though Smith had initially painted southern landscape scenes that were fraught with references to emancipation, his shift towards a celebration of military heroism reflected the evolving culture of post-war reconciliation movements. Taken together, these four papers demonstrate previously unconsidered aspects of the complicated visual history and legacy of the Civil War. The panel’s audience will include scholars of slavery, the Civil War, cultural history, social history, and art history.