High Stakes, High Hopes tracks the building of urban theorizing in a decade-long urban research and teaching partnership in Cape Town, South Africa. An argument for collaborative urbanism, this book reflects on what was at stake in the partnership and its creative, and at times, conflictive, evolution. High Stakes, High Hopes explores what changed in learning when teaching and assessment occurred in university classrooms, township streets, and ordinary people's households. Oldfield explores how research and assessment were reshaped when framed in neighbourhood questions and commitments, and what was reoriented in urban theorizing when community activism and township struggles were recognized as sites of valid knowledge-making. Oldfield traces the multiple personal and political relationships at play, exploring the shifting patterns of power in this productive, yet always negotiated, collaboration. This innovative methodology reveals the ways in which activists, residents, students, and the author experienced and reworked the differences between them. High Stakes, High Hopes shares forms of practice, grounded in teaching, to train a next generation of urbanists to engage the city embedded in multiple publics and politics across the city. The book builds upon an archive of alternative kinds of urban knowledges, experiments which work to inspire more varied forms of urban theorizing.