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Asian Americans are significantly underrepresented in U.S. school and professional sports, facing barriers rooted in cultural stereotypes and systemic exclusion. This qualitative study explores the intersection of Diversity, Equity, and Inclusion (DEI) in sports and educational leadership by focusing on Asian American participation in New York school sports. Using field observations and semi-structured interview with Asian American coaches and retired student-athletes, the reserach investigates the impact of athletic participation on leadership development, the barriers faced, and strategies to increase inclusivity. Findings aim to inform leadership practices in creating equitable opportunities in sports, addressing stereotypes, and fostering leadership development for underrepresented communities in educational settings.