This research was conducted to understand how 30 American school leaders managed during the COVID-19 pandemic. This qualitative study used a case study approach. The researchers utilized a convenience and snowball sampling to conduct Zoom interviews in May 2020. The research findings revealed that leaders encountered numerous difficulties related to having to lead during two crises (a global pandemic and social-racial issues). Findings also indicated that leaders altered their style and used many strategies to lead in times of crises: They emphasized communication, became stress managers and cheer leaders, focused on developing a sense of belonging among teachers and students alike, and planning for the school year. This study is significant because it expands leaders’ understanding of how to manage schools in times of crisis. When leaders lead effectively during times of crisis, then learning, teaching, and well-being will be less negatively impacted. The implications of this research also invite educational stakeholders to reimagine how to lead in an increasingly technological world. This study is relevant for K-12 leaders, but results could also be useful for leaders in a variety of contexts.