This narrative study examined how the life experiences of high school administrators impact how they conceptualize and understand school discipline. These experiences were then positioned within the current context of COVID-19 pandemic related school closures and protests associated with George Floyd's death which brought light to systemic racism prevalent in school codes of conduct to determine how these events changed their disciplinary practices. Semi-structured interviews were conducted with eight administrators from suburban schools in the New York metropolitan region that also had a minority student population of at least 10%. Transcripts were analyzed using in vivo and process coding to identify themes across the interviews. Three themes were identified: elements that lead to an initial understanding of school discipline, how these initial practices change over time, and the twin impact of COVID-19 and protests highlighting systemic racism causing a drastic change to how administrators respond to student misbehavior. These findings were then analyzed using Critical Race Theory and situated among the current literature. The first finding was centered on the understanding administrators use their personal experiences as both as student and teacher to establish their understanding of school discipline. The second finding uncovered an awareness that in order to address student behaviors, administrators develop stakeholder connections. Lastly, there was an awareness and discovery that codes of conduct in their respective schools contributed to disproportionate discipline. While some administrators had already been working to enact change, others were in the beginning stages of learning about this problem and were unsure of the next steps. Form these findings, recommendations for practice and research were proposed. [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://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]