As community benefits agreements (CBAs) become more common in urban redevelopment, they are generating conceptual confusion and political controversy. Planners who encounter CBA campaigns in practice have limited means of evaluating CBAs’ desirability and likely impact without a more complete understanding of how they interact in practice with municipal government leadership and policy. This paper examines four urban redevelopment projects in which community benefits agreements have been enacted by some combination of community organizations, legislators and developers. While much of the expository literature on community benefits agreements is focused on the inclusivity and political moxy of local organizing coalitions, I find that three additional factors influence a CBAs’ likelihood of delivering promised benefits and opportunities to low and moderate-income families affected by urban redevelopment: the health of the real estate market in the city where the agreement takes place, the role of organized labor in the development politics of the locality, and the extent to which local government participates actively in implementing CBAs and institutionalizing their goals in the public sector.