In this paper, I examine the desirability and effectiveness of appointing in predominantly White institutions of higher education diversity leaders who possess privileged social identities. I conclude that the desirability and effectiveness of such individuals depends on their ascribed identities (especially in terms of race, gender, class, and sexual orientation), the prospective leader's degree of understanding of the nature and functioning of oppression, the institutional history and context, and the broader sociohistorical context in which the institution is embedded. Thus, there will be some situations where appointing diversity leaders with privileged identities can be both desirable and effective. (Contains 1 footnote.)