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This paper foregrounds the developmental capacities leaders need to most fully enact an interconnecting, collective approach to justice-centering educational leadership. Specifically, it offers a portrait of (a) the complex practices leaders employ in service of greater mutuality, interdependence, and coalition building, (b) leaders’ pathways toward increasingly expansive meaning making about justice and equity, and (c) the challenges they face in these efforts. Drawing from in-depth qualitative interviews and developmental assessments with fifty diverse educational leaders across the United States, our study adds a new, developmental dimension to understandings of social justice leadership, and provides novel implications for leadership preparation and in-service learning aimed at growing leaders’ internal capacities for futurity, interdisciplinarity, and transformation in complex times.