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The evolution and trends of special education and educational leadership are evident, especially in recent years. The former has strived to provide equitable educational opportunities to students with disabilities. The latter has dealt with how people in positions of authority in K-12 schools create policy, use resources, and influence other people to achieve educational goals. Together, these notions constitute an idea that school leaders and administrators can provide insight, oversight, assistance, and guidance toward creating educational environments for students with and without disabilities. This chapter examines the current state of special education and educational leadership by exploring the evolution of special education, relevant legal cases, and the enactment of inclusive education. Furthermore, this chapter addresses contemporary issues for leaders, such as the influence of the COVID-19 pandemic, while dealing with special education and the increasing pressure from families for equity for students with disabilities.