Since the mid-1900s, municipal parkland acquisition in North America has occurred largely through the development process. This paper asks how well Toronto’s existing acquisition tools and policies are meeting the needs of present and future populations in the downtown. Research was conducted through a review of the literature, policy and budgetary analysis, and twelve key informant interviews with municipal parks staff, councillors, developers, a planning consultant, and community advocates. The research finds that there are many factors that have impeded parkland acquisition in the downtown, including lack of a strong planning framework, historical disbursal of cash-in-lieu funds city-wide, governance challenges, underfunding of existing operations, limited land supply, a perception of land as overpriced, inability to purchase at market price and in a timely fashion, and limited knowledge of existing tools. The paper acknowledges what has worked and concludes with recommendations to improve the City’s parkland acquisition and development framework.