Debates over safe spaces and trigger warnings have become a regular part of campus discourse, especially in context with discussions over free speech, intellectual freedom, and the role that universities play in the social formation. In particular, the University of Chicago entered into the public fray surrounding safe spaces in the fall of 2016 with the publication of Dean Jon Ellison’s letter to incoming Freshman students. I argue that the internal colorblindness of Dean Ellison’s letter makes invisible the external racial inequalities of admission and participation at the University of Chicago. For those nonwhite students who happen to fit the university’s profile for admission, they may find a discursive and academic environment that at the one hand embraces a diversity of thought and yet adopts a market-oriented approach discourse which invariably positions them in unequal positions of power to pursue the freedom of inquiry and expression.