The purpose of this article is to illustrate Professor William L. Boyd's insights into the political ecology of schooling and his contributions and collaboration with others concerned about ensuring the well-being of students, families, and communities. Over his career, Boyd investigated the subtle and complex organizational constraints to school-linked coordinated services, including examining the reasons for the unrelenting resistance of public organizations to change, despite repeated efforts to reform them. We trace the history of the community schools movement and explore the influential, and at times prophetic, scholarly contributions of William L. Boyd to the research and discussion on the effectiveness, challenges, and future promise of this reform strategy. We hope that current and future researchers can learn from and build on his scholarship to develop new pathways to improve the lives of at-risk children. (Contains 5 footnotes.)