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There has been significant research on teacher retention over the past several decades. Studies have theorized the reasons behind low teacher retention rates including increased workload, burnout, inadequate compensation, and poor leadership. This study builds on The Four-Capital Theory of Teacher Retention (Mason & Poyatos Matas, 2015) in the novel context of school leadership, to gain an understanding of how leaders, crucial curators of successful school environments, understand and facilitate the acquisition of teacher “capital” for retention. Findings suggest that leaders primarily value social and structural capital for retention purposes, as these capitals can be largely influenced by principals and superintendents in their policies and practices. The strategies identified in this study can be applied to various school contexts.