The concurrent crises of climate change, a pandemic, and social unrest have laid bare systemic inequities in our economic, health, education, and criminal justice institutions that negatively impact people of color. School leaders face unprecedented challenges as they navigate these dilemmas and are compelled to address the implicit biases and resulting behaviors and policies responsible for the opportunity gaps in their schools. A path to equitable educational opportunities for all students in an era beset with compounding crises can begin with a new focus on character and virtues to provide a framework for right action. This prioritization of character and virtues dates back to nineteenth-century American educator Horace Mann, who asserted that the goal of public education should be to instill character and civic virtue. Our proposition that the philosophical analysis of character and virtue can be an effective framework for leading for educational equity is followed by an example of how this form of advocacy is utilized by a school principals' group founded in Minneapolis, Minnesota, the "Good Trouble Principals."