Our ecological engagement in this chapter wonders speculatively with historical materialist, Indigenous, Black, and racialized perspectives to negotiate dynamics of racial capitalism in settler colonialism, through movement, reflexivity, and affective contingency. We respond to three artists’ works: Peter von Tiesenhausen’s Peter’s White Picket Fence, or Lifeline, halts the construction of a gas pipeline through his land; Kara Springer’s Repositioned Objects exhumes modernist structures and legacies of bodily and national boundaries; Jin-me Yoon’s crawling series, in Canada, Japan, and Korea, conjectures the complexity of place without recourse to proprietary inscriptions. Theorizing affect and ecology via racial capitalism with Indigenous, Black, and racialized perspectives is key to intervening in the multifaceted coercions entailed by North American “whiteness as property.” The study of ecological art on the lands currently called “Canada” needs a ground of speculative and affective theorizing, generated in anticolonial and collaborative worldviews and praxis.