The urban studies and planning literatures largely conceive of community organizations as either clients of neoliberal regimes or the advocates of marginalized communities. Whereas the first emphasizes structural constraints, the latter focuses on the conditions that permit organizations to exercise agency in planning arenas. This theoretical paper suggests that both frameworks reveal important mechanisms but belie the contradictory pressures facing community organizations. We turn to organizational and social movement literatures to argue that community organizations face two competing forces stemming from resource needs. First, they need money to maintain a staff and finance basic operations. As these are nonprofit organizations, money typically comes from external private and public grants. Second, for communities to support organizations and delegate them representative functions, the organizations need to be considered legitimate by the community. Though community organizations need both money and legitimacy, these resources conflict with one another. Too much dependency on external funders can undercut an organization’s legitimacy to represent community interests in an autonomous and unconflicted way. Too much autonomy from external funders can enhance the legitimacy of organizations, but it can also result in financial destitution. Thus, rather than conceive of community organizations as structural puppets or the voice of the people, we suggest that most are positioned in a contradictory field that pulls them in conflicting directions.