In this chapter, the author offers some themes that emerged from a set of conversations that he had with six student affairs leaders. The leaders faced an array of challenges involving athletics, academic discipline, cultural identity, institutional image, personal attributes, policy, residence life, and state politics. Their challengers were trustees, presidents, politicians, and students. The author hoped to construct a small case study about challenges to the integrity of student affairs leaders from those conversations. As with any qualitative case study, the purpose was to generate hypotheses rather than to test them.