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Employing a theoretical lens that critically examined organizational culture and leadership, this paper summarizes ethnographic research conducted on the retention of first-time freshman cadets at a senior military college in 2019. The purpose was to explore whether the organizational culture and leadership styles influenced cadets to leave the corps of cadets. Hence, culture was used as the conceptual framework, and leadership as the theoretical framework. Thirteen narrative interviews, observations during new cadet orientation, and a review of official cadet program-related documents were used to conclude that the first-year experience for cadets consisted of a highly transactional leadership culture that influenced some cadets, including minorities, to drop out or to consider dropping out of the cadet program during their first year.