This teaching case study aims at encouraging meaningful conversations about discipline. The case illustrates the increasing need for school leaders to adopt discipline approaches that foster support, equity, inclusion, and advocacy for cultural differences rather than punishment and the exclusion of marginalized students. This scenario takes place in an urban middle school that is representative of many other American schools. In particular, I examine the challenges educational leaders commonly face with discipline, leading to unsatisfactory student learning outcomes and well-being. The hope is to expose school leaders to a holistic discipline approach that is grounded in support, care, love, and respect for cultural diversity. To promote reflection, I pose questions designed to prepare prospective and current educational leaders facing similar discipline situations.