The purpose of this study was to examine, understand, and describe the life, leadership, and influence of Dr. James Edward Scott on higher education and more specifically student affairs; as one of the most well-known and respected African American male chief student affairs officers in the late 20th and early 21st centuries. Using a qualitative research approach as the method of research, this study utilized elements of inquiry to illuminate the experiences of Dr. James Edward Scott. For its biographical components, this study employed a narrative approach to qualitative research methodology to determine the realities that existed within Scott's leadership journey. A narrative approach was also utilized to frame chronologically the experiences and stories presented through the data collection process. In an effort to reveal Scott's leadership journey, this study examined leadership theories, philosophies, and development. Theories and philosophies--such as transformational leadership, authentic leadership, and learning leadership--were reviewed and analyzed as the main theoretical framework for leadership within this study. Leadership and management experiences of African Americans as well as the barriers, challenges, and organizational dynamics that influence their professional journey or career matriculation were also explored. The executive position of chief student affairs officer was also examined for its characteristics, role, and function, along with an overview of collegiate student affairs. Because Scott was a member of an historical African American Greek organization, literature emphasizing the leadership influence of African American Greek letter organizations was reviewed. Critical race theory (CRT) was also reviewed for its role in analyzing this study to understand Scott's experiences and stories. For Scott, his leadership was not a formality of his profession; it was a way of life demonstrated in his day-to-day interactions with people--not just with students and staff members, but individuals--within the communities in which he lived. When considering Northouse's (2010) trait versus process leadership, Scott's skill for goal-setting and planning for the future was not a biological imperative; it was mindset expressed in his words and translated through his actions (pp. 4-5). Scott's true leadership journey was not one of managerial idiosyncrasies that are often defined by paper pushing, budget calculation, and performance evaluation; it was one of the heart, with relationship ties and commitments that bind individuals and celebrate the accomplishments and innermost attributes of others, which in many cases were students, staff members, and colleagues. As an inspirational leader, Scott's legacy lives through many of the organizations for which he bestowed his talents: the University of Florida, Omega Psi Phi fraternity, and NASPA. In spite of Scott's awards and honors, his achievements in student affairs as a professional are only masked by his character and willingness to be in service to others. Ultimately, though Scott rose to a position of leadership and authority, his legacy lives beyond it and continues through the passion of others. [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://www.proquest.com/en-US/products/dissertations/individuals.shtml.]