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Followers grant legitimacy to leaders whom they perceive to be a good fit for the role, yet the conceptual framework for this study illustrated how dominant discourses related to gender and leadership continue to negatively affect a woman's potential in achieving legitimacy as an academic president. This study examined the predominant discourses taken up by women during their inaugural addresses to legitimate their role as leaders of the colonial colleges - a unique sample of institutions because of their long legacies of male leadership and strong organizational sagas deeply rooted in masculine preferences and cultures. The inaugural address represents a celebration of the organizational saga while also being a challenge of discourse for any new leader in establishing legitimacy before becoming fully incorporated into the institution's community. By applying a feminist poststructural approach to discourse analysis, the methods of this study involved multiple phases of deductive and inductive coding of the speeches along with a parallel interrogation of the data which revealed gendered subjectivities that positioned the women in this study as relatively powerful or powerless in their quest for presidential legitimacy. The conceptual model that emerged from this analysis illustrated how the negotiation of gendered discourses and the accommodation of discourses related to institutional, environmental, and moral legitimacy positioned the women as relatively powerful in their speeches, and thus, charted a course for navigating the male preserve of higher education leadership. Perspectives provided from this study challenged the dominant discourses of gender differentiation and expanded the discourses available to those aspiring to the college presidency. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]