The purpose of this concurrent, nested, mixed-methods case study was to trace the evolution of the multigenerational success of the winningest college football coach of all time, John Gagliardi, to identify potential leadership styles, characteristics, and coaching effectiveness methods that others in a multigenerational leadership role may use. The goal of the study was to identify and examine the leadership characteristics of this exemplary coach, who has continued to succeed in coaching college football for six decades, across four generations, with the intent of identifying characteristics of successful leadership. Sixteen participants took part in interviews and a survey: two players and one assistant coach from each decade starting in the 1950s. To gain the breadth and rich description desired, standard qualitative research methods, semi-structured interviewing, and the Revised Leadership Scale for Sport survey were utilized to collect data to assess the leadership characteristics and assist in the interpretation and emergent theme development of the data. Based on the analysis across generations, four distinct leadership themes emerged: coaching efficacy, effective communication, the professional will to win, and empowerment. All four traits carried relatively equal importance, based upon the collected data across the participant generations. The leadership characteristics witnessed over time by the players and assistant coaches, coupled with the data analysis from the interviews and surveys, provided an indication of how the coach might have achieved such success. [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.]