This article presents an analysis of the limits of “power to” and agency through an examination of the Barry administration in Washington, DC. I begin by asking why this administration, born of the civil rights movement and tremendous optimism, was unable to live up to its expectations. I provide an in-depth examination of Barry's efforts at reform, his popular appeal, and his appeal to business within the context of Washington's local political history. I find that Barry's power was constrained by a combination of structural factors, personal choices, the legacy of racism and racist exclusion, and a failed identity-deployment strategy. The findings have broader implications for the use of identity-deployment strategies for minority political leaders generally.