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Despite scholarly agreement that the Flying African myth has emerged throughout the Americas from every location with a history of transatlantic slavery, this article is the first to analyze that myth in Canada. Taking this scholarly absence as evidence for larger erasures of Black culture in Canada, I trace variations of the myth in order to reframe the nation's ambivalent history of transatlantic slavery. Dominant narratives commemorate the Underground Railroad while ignoring the country's longer collusion in slavery and racial oppression. Comparing iterations of this myth across Canada—and considering these in light of Caribbean, Latin American, and US versions—offers a unique opportunity to theorize the relationships between nation, diaspora, and the histories of transatlantic slavery. Moreover, the multiplicity of identifications and definitions of Blackness in Canada offers a particularly salient microcosm for theorizing the diaspora writ large. In particular, I consider the Flying African myth within the specific context of Black Canada to expand on Gilroy's project in The Black Atlantic: Modernity and Double-Consciousness.