This article explores leadership lessons that can be drawn from popular sport icons. These lessons reveal how athletes leverage their status to drive social change or how they inspire others through performance-based practices that align with effective modern-day leadership skills. We present four cases to illustrate key leadership competencies that can be gleaned from the nuanced ways these popular sport icons operate within and beyond sport. These include adaptability, emotional intelligence and humility, collaboration and inclusivity, and purpose-driven, values-based leadership. Recommendations for pedagogical approaches to leverage these leadership lessons include discussion-based activities, active learning experiences, and creative expression. While acknowledging potential limitations and challenges, we show how the accessibility and resonance of sport icons can be a powerful access point for leadership education and development.