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Initiatives around anti-racism education in the secondary school system are presently insufficiently applied, particularly in recognizing Shadeism and its impact on the behaviour, academic achievement, and social engagement of students. This chapter hypothesizes that the closer in proximity to Whiteness of the student, the greater their access to White privilege. Obeyesekere situates the idea of Shadeism in the colonial context and establishes its present day implications on racialized secondary school students in the Greater Toronto Area (GTA). Shadeism is deconstructed using critical anti-racism theory (CART) in order to examine its consequences on urban students (Dei, 2011). Drawing upon research from anti-racism scholars, Obeyesekere grapples with the question of how Shadeism affects students in the supposedly post-colonial world. It is proposed that Shadeism can be addressed in schools through the multifaceted implementation of CART, in order to create an inclusive and engaging learning environment for all students. The chapter recommends strategies to address the consequences of Shadeism on students through the exploration of a three-tiered initiative. The initiative proposes to encompass and concurrently apply; a ministry and board-wide culture change, teacher training, and holistic student programming. The focus of this chapter is on student programming.