High fee-charging non-government schools for boys comprise a small but significant sector of the Australian schooling market. In different ways in different historical periods these schools have represented themselves as being concerned with more than just an instrumental or utilitarian education, making both explicit and implicit claims about the kinds of values they work to instill in their students and the kinds of men they aim to produce. This article looks closely at one such school in order to gain an understanding of how it sought to shape a particularly classed, leadership-oriented masculinity, during a period of institutional change. The historical context for the study is the final decade of the twentieth century, a period that saw the approximate beginning of a "boys' crisis" in Australian education, which for schools like the one in this study meant a degree of reconceptualisation of practices and ideologies of masculinity. The article draws on a set of oral history interviews with former students and executive staff of the school. (Contains 3 notes.)