This dissertation follows the trajectory of two football programs, the University of Wisconsin and the University of Pennsylvania, primarily from the perspective of administrators. It spans roughly forty years, from 1930 to the early 1970s. At first glance, these two schools may seem unlikely points of comparison, but viewed together they provide valuable insight into the history of intercollegiate football. Prior to 1950, they fielded teams that were very similar in size and stature. In fact, they often played each other. After the Ivy League officially formed in 1954 the programs were clearly on different trajectories, but neither path was predetermined nor without surprising detours. By comparing the two universities' programs a number of themes emerge, including the importance of institutional branding and identity formation, alumni relations, conference building, and the evolving role of university presidents. It is clear that while administrators during this period had more latitude in determining the course of their football programs than they do today, they were largely constrained by institutional and cultural factors. Individual skill at navigating the rocky terrain of college athletics was also important and could mean the difference in whether a president flourished or was cast aside as a result of his athletic policies. [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.]