The “urban” mathematics classroom has become an increasingly polarized site, one where many middle-class White teachers attempt to bridge the divide between themselves and their relatively economically disadvantaged, non-White students. With its mania for high-stakes testing, current education policy has intensified the importance of mathematics in the school curriculum—both drawing attention to and reifying an “achievement gap” between White (and Asian) and non-White students (Martin, 2009c, 2010). Keeping in mind the Mathematics for all rhetoric as it affects the academic and life success of students (Martin, 2003), this cultural polarization in the mathematics classroom provides a rich site for exploring pedagogical practices that might improve mathematics achievement and persistence for all students. As a middle-class White man, I am a teacher in such a divided situation; I have spent the past 7 years working with almost entirely Black 9th graders as a mathematics classroom teacher in an urban high school. In this study, I employ a critical postmodern theoretical perspective (Stinson, 2009; Stinson & Bullock, 2012) toward an autoethnography (e.g., Ellis & Bochner, 2000) of my experiences as a teacher in this particular educational environment. Using writing as a “method of inquiry” (Richardson, 2000), with an emphasis on two particular intersections of critical race theory (e.g., Tate, 1997) and poststructural theory (e.g., St. Pierre, 2011)—the role of storytelling and the concept of “race” as metanarrative—I examine, theorize, and (re)tell of my life and teaching experiences. My aim is to provide assistance of sorts for a new teacher in a similar situation; the kind of educator—middle class and White—who, according to projections, will more times than not be filling the role of teacher in the urban mathematics classroom. The goal of this study is twofold: (a) to gain and share theoretical and practical insight into my teacher identity and pedagogical practices, and (b) to provide potential insight for and assistance to other mathematics teachers who may see themselves in the (re)telling of my stories.