This paper explores the role of urban planning policy, urban housing policy, and urban design on master planning. Though master planning as a concept has historically been tied to urban design, this paper argues that this notion is fundamentally flawed, and that urban planning policy and housing policy play an equally important role. This topic is explored through a case study analysis of Stuyvesant Town and Regent Park, master-planned affordable housing projects in New York City and Toronto, Ontario. With a focus on process, policy, and design, this paper will discuss how interpretations of master planning in New York and Toronto influenced the development of both housing projects. A comparative analysis of both projects highlights the multi-faceted nature of master planning, and demonstrate the importance of urban planning policy, housing policy, and urban design ideologies to master planning.