Discretionary planning supports the provision of public benefits when changes in zoning create additional value on private development sites. This paper draws on two case studies in Toronto, exploring how discretion shapes the broader political and planning policy context in which public benefits are secured from private development. The cases show that even within the same city planning department, variations exist in the application of discretion in planning decisions, which lead to different approaches to securing public benefits. Discretionary planning tools, such as density bonuses, are of consequence for political conflicts over local priorities, democratic accountability, and the built environment.