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This study examined the persistent gap between school districts' leadership diversification efforts and the lived experiences of leaders of Color (loC). Despite substantial investments in targeted recruitment, inclusive practices, and leadership pipelines, districts like Cascade Hills School District struggled to retain loC due to the systemic racialization of policies, practices, and cultural norms.. These well-intentioned efforts often failed to address the underlying issues of exclusion and undervaluation faced by loC. The study used Ray's theory of racialized organizations to highlight how organizational structures and implementation practices perpetuate marginalization, affecting loC's sense of belonging and agency. Findings underscore the need for more effective and genuinely inclusive practices to support loC and bridge the disconnect between diversity initiatives and their practical implementation.