This article presents a phenomenological study of teacher-assistant principals (teacher-APs) in Catholic elementary schools. Drawing from player manager and role theories, this article describes the lived experiences of these individuals, particularly how they perceive the benefits and constraints of their unique role in both faculty and administration. Analysis of participant interviews reveals three heuristic models of the teacher-AP experience: boundary teachers who ally more closely with faculty; boundary administrators who take on a more executive identity; and player-managers who equally participate in, and perceive to bridge, the administrative and faculty spheres. Findings also suggest that the experiences of these teacher-APs are highly dependent on the current principal and his/her perceived administrative needs.