Between 1998 and 2003, Canadian courts were confronted with two cases that have held significant legal and political consequences for Aboriginal peoples. The cases, R v Gladue (1999) and R v Powley (2003) raised pressing questions about Aboriginal identities and the rights and material resources that follow from legal recognition. In one form or another, these cases have generated important legal, political, and theoretical questions that require some exploration: How has ‘Aboriginality’ been legally constituted within Canadian jurisprudence? In what ways have these racial-legal definitions changed temporally and geographically? And finally, and most importantly, who can legitimately make claims to Aboriginal identities and to the legal rights and material resources that accompany the law’s recognition of difference? In this article, I historically contextualize these contemporary debates around the juridical construction of Aboriginal identities in Canadian jurisprudence. My substantive focus is two trials that took place between 1923 and 1925 and which centered on competing territorial claims to Stanley Park, an urban park in Vancouver, British Columbia. The cases involved eight mixed-race families of Aboriginal and European ancestry who had lived on the land in question for three generations, and whose ancestors had been there since time immemorial. A central question that emerged throughout the juridical and extra-juridical discourse is if these people were ‘Indians’ (or ‘squatters’) and whether they could make territorial claims through Native title. Through these cases I suggest that the current controversies over Aboriginality evident in Gladue and Powley are deeply rooted in colonial legal processes and practices that require some historical analysis. Ultimately, historically grounded questions about the law’s constitution of Indigenous identities may provide us with important insights into the many facets of colonialism and its residual legacies.