High school administrators in the Carter School District (CSD) are aware of the negative impact exclusionary discipline has on students, but they exclude students anyway. This study used qualitative methods to answer the following research questions: How do high school administrators in CSD describe and explain their discipline decision-making? How do high school administrators in CSD describe and explain their decision-making as it relates to determining the length of an expulsion? How, if at all, do social, cultural, and structural considerations influence the discipline decision-making of high school administrators in CSD? Interviews with eight administrators were analyzed, using a grounded theory methodology. The theory developed explains the contrast between punitive and restorative approaches to school discipline in terms of cooperation, power, and length of school exclusions. Results indicate that the more students power with administrators toward accountability, the more likely it is that a restorative approach to discipline is taken. The less students accept social responsibility, or the greater the safety risk associated with a discipline incident, the more likely it is that control is asserted through a punitive response. This is true for choosing exclusionary versus non-exclusionary discipline and the length of exclusion. Administrators expressed concerns about disproportionality for marginalized student groups in discipline, but did not describe systemic anti-bias, antiracist actions taken to meaningfully mitigate those concerns. Administrators favored restorative approaches to discipline, but perceived staff to favor punitive approaches. This goal divergence related to the purpose of school discipline, coupled with the absence of a shared understanding of justice and accountability, caused tension and may be useful in understanding which leadership practices are necessary for uniting school staff toward a common goal for discipline, leading to more equitable outcomes for historically marginalized students. [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/en-US/products/dissertations/individuals.shtml.]