This Article addresses the extent to which public officials can or should attempt to settle constitutional claims and concerns by privatizing, taking, or otherwise disposing of public properties. The practice, which the Article calls settlement-by-disposition, raises fundamental questions regarding the nature of constitutional liberties and the scope of governmental control over public properties that are critical to their effective exercise. Settlement-by-disposition has gained considerable attention recently, in large part owing to efforts by local and federal officials to settle Establishment Clause controversies by selling, taking, and otherwise disposing of public properties. But settlement-by-disposition is a much broader concern. It has also affected speech and assembly rights, as officials have increasingly privatized or otherwise disposed of public forum properties such as streets, sidewalks, and parks. Although the historical connection has not generally been made by courts or commentators, settlement-by-disposition was actually a central tactic in the campaign of massive resistance to racial integration. During the civil rights era, public officials disposed of public parks, pools, and schools, often in an effort to thwart desegregation. The Article applies the lessons of the civil rights era to settlement-by-disposition in contemporary First Amendment contexts. It develops a framework for assessing the constitutionality and propriety of settlement-by-disposition. The framework is based on a quasi-public property metaphor. The subject properties are critical constitutional assets held in trust for the benefit of the public. The Article argues that public officials (and, in some cases, their successors in interest) owe duties under the trust of fair dealing, preservation, and compliance with constitutional covenants that attach to and run with the land. Ultimately, they are obligated to enter constitutional rather than nakedly political settlements.