This paper situates recent school-to-work transition policy in Ontario, Canada, within the historical context of secondary school reform in the past 50 years. This understanding informs our analysis of interviews with representatives from government, business, organised labour, education and partnership brokers. Data suggest tensions between the rhetoric of corporatism and the reality of a market model, the rhetoric of enhancing opportunities for all students and the reality of lower graduation rates associated with new curriculum. We argue that these tensions reflect historical and continuing struggles around education and training and the adoption of neo-liberal policy approaches that decrease rather than enhance opportunities for non-college-bound students.