This study investigates the outcomes of two novice preservice teachers' (PSTs') attempts at taking up the roles of critical guides (Damico & Apol, 2008) to mediate discussions about racism in response to President Barack Obama's (2008) campaign speech "A More Perfect Union." With the objective of teaching for social justice, these PSTs initiated their discussions in two senior English classrooms at the same high school located in a predominantly white, economically low-middle-class Midwest community. Profiles of each intern were developed from data comprised of field notes, meeting notes, interviews, video and audio recordings, journal entries, essays, and other artifacts. Framed by Damico and Apol's (2008) concept for mediating historical risky texts, and grounded in the principles of critical literacy and antiracist pedagogy, this investigation demonstrates that despite their objective to teach social justice, the PSTs enacted discussions that generated shadow texts (Simon, 2000) and perpetuated stereotypes. It suggests that for these PSTs, there may be a disconnection between the theories they learned in their teacher preparation courses and their practical application of such theories in the field. (Contains 5 figures.)