Small, private colleges provide an essential element to the landscape of higher education, offering intimate class sizes and high touch experiences for traditional college populations. The president of a small, private college must wear many hats, both to the internal campus and external community. Presidents set the tone for leadership and communication, devise strategic plans, and select staff to accomplish those initiatives. With fewer layers of administration, the president of a small, private college also has greater influence on day-to-day operations than their counterparts at larger institutions. Athletics at the small, private college is an important component for enrollment, campus life, and budget. At institutions that do not provide athletic scholarship money, student-athletes account for significant portion of undergraduate populations. NCAA Division III institutions, mostly small, private colleges, incorporate athletics into campus life and position the student before the athlete. The presidents of these institutions are poised to thoroughly understand how athletics influences the small, private college landscape. This research was designed as a multiple case study, examining five presidents of small, private colleges. Each president served as a case, and research was conducted through two semi-structured interviews and document collection. Following individual case analysis, cross-case analysis occurred where three overlapping themes emerged: the president’s influence over managing tension with faculty, winning builds a foundation for success, and agility is necessary to respond to changes. The implications of the research project demonstrated that small, private college presidents must make decisions about athletics in alignment with institutional missions and the strategic plan, allowing a strong connection to the organization’s culture.