The global economic downturn and high youth unemployment have created a challenging context for Ontario secondary-school teachers to meet the compulsory half-credit career studies course objectives intended to support school-to-work (STW) transition. Bronfenbrener's (1979) ecological systems theory provided a clear framework to examine influences and knowledge one teacher used to support the teaching of career studies. The data showed that the teacher knew her local economy had been affected by the global economic downturn, and she described local business closures and the potential impact upon employment opportunities. The teacher understood the impact upon her students and explained the importance of students understanding these connections. The open level of the career studies course necessitated the meeting of diverse student needs, including students with disabilities, widely ranging academic levels, and those at risk. This study aids our understanding of how the GLC20 teacher might contribute to successful STW transition for all students in times of global high youth unemployment.