This study examines senior student affairs leadership through the diverse lenses of subordinates, administrative peers, presidents, and senior student affairs officers (SSAOs). Guided by an interpretive paradigm, a qualitative methodology was employed consisting of a six-case comparative analysis and grounded theory approach. The findings provide a comprehensive portrait of the key factors associated with developing and maintaining trust in SSAO leadership. (Contains 3 figures, 1 table, and 1 footnote.)