Large-scale redevelopment projects such as Boston’s “Big Dig” bestow numerous public benefits—often without charge—to nearby property owners. In the case of the Big Dig, these benefits include twenty-seven acres of newly created parkland, where once an elevated freeway stood. Beyond the immediate and obvious beneficiaries are nearby landowners seeking “better zoning” that might include a relaxation of maximum height or floor area ratios to enjoy the new view. This Article explores the often hidden impact of the nearby landowners’ means of accomplishing their desired result: bargaining with municipalities for private, derivative benefits. The Article compares legislative and judicial responses to land use bargaining in California and Massachusetts, states with dramatically different approaches to land use planning. The Article concludes that bargaining in the absence of a guiding land use plan—the Massachusetts “model”—results in a chaotic land use policy and unpredictable development.