This study aims to understand how Black educational leaders experienced colorism and how they perceive colorism affects Black students today. A lot of research has been conducted on colorism in the greater social system, but little has been done in the context of education. The study consisted of eight Black urban administrators who through their experiences spoke to how they see colorism in the educational setting. Through interviews the participants articulated their experiences that later would be categorized from the adult perspective or student perspective. This study sheds light on the issue through a qualitative, phenomenological case study using personal testimonies and experiences while creating scholarly dialogue to ensure the students of today and tomorrow have all of the opportunities to be successful in a modern-day classroom. With an increasing number of students of color entering the education system, educators need to understand what stereotypes and biases they might be carrying into the classroom. Educators also need to be aware of biases that might occur for students in their social interactions with each other. Furthermore, it is necessary to understand how these issues could impact student success and achievement. The study yielded five major themes: Educational Influence, Emotional Influence, Experience Based on Color, Historical Context, and Mentality Influence. Through these themes the participants experience with colorism was chronicled. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]