This paper attempts to examine some of the broad political aspects of the preservation process in Chicago by recounting a number of significant historic preservation controversies that have arisen over the past decade. The preservation of historic resources has taken on increasingly greater importance as Chicago is seen by City officials, residents, business leaders, and tourists as a world class city. Over the past decade downtown has expanded and evolved into a 24/7 area complete with residential, retail, service, and office uses and the neighborhoods both near and far have undergone redevelopment. During the same period many of the City’s neighborhoods have undergone a treat deal of revitalization, while others have declined or remained stagnant due to unfavorable demographics, inertia, and lack of an identifiable constituency and political will. Preservation efforts have in many ways mirrored these successes and failures, though in some cases, redevelopment results in demolition and failure in benign neglect or worse. So why are some efforts successful and some not? There appears to be no consistent resolution to some preservation controversies.