Michael Pelligrino is a novice principal in a large urban high school. After a rocky yet somewhat successful first year as the principal of Hilltop High School, tensions in the school and surrounding community are at an all-time high. The deaths of unarmed Black men, women, and children by law enforcement agents nationwide have led hundreds of students to participate in community-led protests aligned with the #BlackLivesMatter movement. Pelligrino is conflicted. Should he respond to the needs of his school community or continue to focus on district mandates? This case study provides opportunities for aspiring school leaders to engage in critical reflection and transformative leadership practices.