Educational leaders at all levels must be prepared to address crises and their aftermaths. The conventional wisdom on crises and their management suggests that while crisis can originate from myriad sources, they largely proceed according to predictable stages. Our study draws from traditional and more critical literature on crisis and crisis management to understand the case the 2017 Unite the Right rally and its impact on Charlottesville City Schools. Specifically, we unpack the unfolding nature of the crisis and the district superintendent's leadership through each phase of the crisis. We use the notion of paracrisis and crisis of challenge to understand how an acute and traumatic experience for the school community evolved into a crisis that challenged the legitimacy of the school district for its history of policy and practices that sustained institutionally racist practices for decades. Our findings illustrate how the process of crisis transformation occurred, and more importantly, how the superintendent's approach to leadership also changed to meet the new demands of the evolving crisis. These findings raise important questions and implications for how educational leaders might think about the crises they face, and the crisis management plans that guide that work.