This article examines the events leading up to, surrounding, and following UNESCO’s controversial removal of Germany’s Dresden Elbe Valley from the World Heritage List in 2009. At the heart of the controversy lay the construction of a new four-lane bridge, the Waldschlößchen Bridge, that would cut through scenic meadows, destroying long-protected vistas and changing the city’s cultural landscape. Although supported by German court decisions and local public opinion polls, the bridge has been denounced by many as an eyesore and an affront to the ideals of World Heritage. Yet despite the bridge, Dresden supposedly maintains World Heritage worthiness, even if it no longer enjoys that title. The author attempts to make sense of these contradictions in order to discover lessons applicable to the World Heritage program as a whole.