This article explores the lack of diversity at the 8 Ivy League institutions using a Critical Race Theory lens. It includes a comprehensive literature review of the scholarship related to diversity in academe, but especially within the areas of elite institutions and administration. The article also provides data pertaining to the senior leadership at the Ivy League institutions juxtaposed with data on senior level administrators throughout the nation, using the American Council on Education's "On the Pathway to the Presidency" report. Lastly, the article provides recommendations to presidents and institutions for bolstering high-level diversity among high level administrators. The authors stress the importance of addressing the historical and current policies and practices that either facilitate or negate the goals of diversity. They also encourage Ivy League institutions to create internal committees or task forces that focus on racial and ethnic disparities in senior administration.