This qualitative study investigated the perceptions of masculinity and fatherhood of male school leaders and their perceptions associated with leadership practice. We used purposive sampling to recruit male Israeli school leaders for participation in the study. We collected the data by semi-structured interviews, which we then subjected to thematic analysis. The results indicate that the participants were divided between hegemonic and caring views of masculinity. By contrast, two-thirds of the leaders held an emotional view of fatherhood, and only one-third had an instrumental view. The results shed light also on the perceived connection of leaders’ masculinity and fatherhood views with their leadership practice. The findings and contributions of the study are discussed.