This study sits at the nexus of American-based Israel education, supplementary education in congregational schools, and research on teachers and the beliefs that inform their practice. Focusing on four American-born teachers in two progressive congregational supplementary schools, the study employed three strategies to develop understandings about each teacher’s relationship with Israel: (1) life history, an examination of a teacher’s personal story, situating it within the social, political, cultural context in which the life story takes place; (2) intellectual biography, creating a record of what a teacher knows about an area of content or practice, how she came to know it, and how that shapes her current understanding of that content or practice; and (3) case studies. The blending of these strategies, along with the employment of multiple appropriate methodologies led to the creation of thick profiles of each informant.