There is a growing body of literature on the roles that deans play in challenging times; however, what is often missing are deans' own voices as they reflect on their experiences trying to manage the dilemmas and crises inherent in their work. This is particularly true of the past few years when deans have managed unprecedented levels of complexity and uncertainty. Using complexity theory as a conceptual framework and case study methodology, the author shines a light on the lives of deans at a large Canadian university as they grappled with issues related to the pandemic and others such as a protracted strike by academic staff. The findings suggest that complexity theory can serve as a useful theoretical lens for better understanding issues such as structural tensions, resistance and non-compliance, the multiple roles of deans, toxic faculty cultures, and trust and mistrust in higher education.