There is an overrepresentation of elementary-age, Black boys being suspended across the United States. Researchers have found that if these boys are disconnected from school at an early age, they are at risk of becoming part of the school-to-prison pipeline (STPP). Educators, particularly those in urban settings, need to understand more about the use of exclusionary discipline policies and practices. The purpose of this generic qualitative study was to understand how urban educators consider the consequences of exclusionary discipline practices and the overrepresentation of elementary-age, Black boys who receive them compared to others. Critical race theory informed this study. Ten administrators who had 2-20 years' experience as administrators working with an urban school demographic were interviewed; all were from one school district in the western United States. Open and in vivo coding were used to support thematic analyses. The urban administrators described struggling to dismantle racist systems in their school cultures. Participants agreed that antiracist approaches, professional development, exposing injustices, and checking bias are important in schools, and they emphasized new ways of thinking and new systems that promote equity for all students. These leaders wanted a better future for students than their communities and society anticipate. The study findings add to the field of research in educational leadership and provide information that administrators of urban institutions can use to develop and implement their strategic goals to address disparities in school discipline by race and reason, which will lead to more racially equitable responses in disciplining Black students, resulting in positive social change. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]