One of the largely undocumented dimensions of public housing transformation in the United States is the multi-sector, multi-organizational collaborations whose charge is to manage the local implementation of mixed-income developments. In Chicago, private real estate developers entered into partnerships with the Chicago Housing Authority to finance, design, build, and manage the new developments. Key topics considered in this paper include the structures and processes of new organizational working relationships that have been established, how they are evolving over time, and the key operational challenges confronted in creating and sustaining them. We argue that these cross-sector collaborations within the context of the privatization of public housing generate complex organizational roles and dynamics that would benefit from far greater intentionality, clarity, and support to promote effectiveness and accountability.