This research project offers insights into the history of European visual representations of Indigenous peoples, Tecumseh in particular, and the larger issues of colonialism and bias with its cross generational and damaging consequences. The investigation examines how visual representations of Tecumseh came into being and remained in circulation across time and to what degree were recorded archival depictions of the leader still raise questions of veracity and intent. Indigenous theorists, Vine Deloria, Jr., Marie Baptiste, James (Sake) Youngblood Henderson provided insights into Indigenous identity, sovereignty and decolonization theories; Stephanie Pratt’s examinations offered analysis of the representation of Indigenous leaders through British portraiture; Elders Edward Benton Benai and Floyd Looks For Buffalo Hand, are drawn on for their cultural knowledge.