This case study explores the challenges faced by incoming principals who encounter unexpected situations along with the impacts on multiple stakeholders of leadership transition on a middle school campus. Leadership shifts are felt throughout organizations in diverse ways and may even have a personal impact on individuals in a school community. Leadership transition, by its very nature, is a change. Change, especially at the top, presents organizations with myriad possibilities and similar stressors. Principal turnover has a direct impact on school achievement. The principal is key to sustainable school improvement, a process that may take 5 to 7 years after a new principal has been named. High-performing principals often leave campuses and move to central office positions because of their success with campus achievement. In the late 1990s and early 2000s in Texas, more than 30% of principals left their campuses within the first 2 years. Principals leave schools for varying reasons, such as promotions to other campuses, district-level roles, new opportunities in other districts, retirement, and positions out of the educational field. The reader should consider all perspectives in the narrative. This case study involves issues related to transition, change, instructional policies, decision-making, staff culture, and the impacts of COVID-19 on student achievement.