Purpose: Using structure-agency theory, this paper highlights how school and district leaders may use their discretion to reshape or reinforce pipeline structures to increase educator racial diversity or to maintain the racial status quo. We also consider how such efforts intersect with structural racism limiting the impact of positive efforts and inhibiting the recruitment and hiring of teachers of color overall. Research Methods/Approach: We used a cross-case analysis approach of four districts aiming to racially diversify their teacher workforce. The study included interviews and focus groups with school and district leaders and teachers of color for a total of 23 participants. Background information emerged from conversations with program coordinators and documentation review. Findings: Structural racism and Whiteness pervaded district leaders' attempts to recruit and hire teachers of color across. Districts created structures aimed at increasing the number of teachers of color in their pipeline, often due to the agency of an individual leader. However, structural racism, frequently reified by front-line educators' agency, most of whom identified as White, frequently undermined these new processes and procedures. Implications: This work suggests the need for further exploration of leaders' conceptualization of diversity and equity. Districts can conduct audits of pipeline practices and provide further training on bias and racial equity. Teachers of color also require support to navigate racial discrimination and should be provided tools to feel empowered to disrupt these systems. Finally, schools should support and hold White educators accountable to counteract bias and create more equitable and inclusive working environments.