In this chapter, focus is directed towards the political dimensions of a paradigm to sustainable transport. This is explored through a case study of 30 years of transport policy and planning in Stockholm, Sweden, with a specific focus on key initiatives, policies and plans for the development of the transport system in the city and the region and the conflicts and tensions that have arisen around these initiatives. Examples discussed in the text include the Dennis package, the Congestion charging trial and recent initiatives for sustainable transport, which are implemented in parallel to conventional road development. The text leads to a principal discussion about the role of politics and the political in the continuous work for a more sustainable transport system.