Despite the fact that African American and other students of color, students labeled as having disabilities, and poor students in urban schools are indisputably linked in terms of the quality of schooling they have experienced, few attempts have been made to examine the relationship between special education and urban education. Both students placed in special education and those who attend urban schools have a long history of being miseducated, under-educated, and treated inequitably by the American educational system, with the American educational system at times excluding these students altogether from receiving a free and appropriate public education. Therefore, the purpose of this article is to provide (a) a historical analysis of special education and the treatment of students with disabilities prior to the "Brown" decision; (b) an analysis of the challenges that students with disabilities, African American and students of color, poor students in urban schools, and students affected by all three have historically experienced in their quest to receive a free and appropriate education in the American educational system; (c) a discussion that illustrates that special education is the new tool for the resegregation of African American and other students of color in special education; (d) a discussion of who the real beneficiaries of failed urban schools are and why they resist providing an equitable education to all children; and (e) specific examples of what it means to go for broke in calling out educational inequities and advocating for African American and other students of color, poor students, students with disabilities, students in urban settings, and students affected by all of these factors and issues.