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This chapter will explore the tensions between irony, solidarity, and humanization in the context of “College Prep”, a public school in Brooklyn, New York. The school created its own in-house nonprofit organization in 2008, which I call “the Foundation,” in order to solicit private sector funds. Through a case study of the head of the Foundation, a White male whom I call Mr. Thomas, I illuminate the conflict between alleviating and perpetuating inequity in education.

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