The community school model is a strategy for addressing educational and place-based inequities. Our case study of a community school in Pennsylvania examines the role of the principal in leading toward authentic partnerships with families and community organizations. Our findings demonstrate how the school principal's approach to partnerships evolved toward expanded notions of student outcomes, fostering democratic dialogue and productive disagreement, building and sustaining relational trust, and negotiating reciprocity for generativity. We conclude with implications and recommendations for educational leadership practices that cultivate working in and with communities. This study contributes to growing scholarship about leadership in community schools.