The purpose of this study is to examine how the varying levels of knowledge and skill in special education affect the school-level leadership of special education programs. This study examines the similarities and differences between principals who are knowledgeable and skilled in special education and those who possess a knowledge base and skill set in special education that is typical for the average principal. In an attempt to gain a deeper understanding of the constructs of effective special education leadership at the school level, special attention is given to how principals are involved in the special education programs at their schools. A two-phase, sequential mixed-methods, multiple-case study design was used to collect data on principals of elementary schools in Alabama (i.e., kindergarten through fifth grade). The principals in this study who are knowledgeable and skilled in special education place a high value on special education and provide students with varying levels of disabilities opportunities to acquire both functional and academic skills through authentic experiences within the natural environment. Principals who possess an average knowledge base and skill set in special education place a higher value on pre-referral interventions and instructional strategies.