This work explores the rise and fall of proposals, which were current between 1945 and 1977, for an inner suburban radial freeway network in Sydney. Conceived in terms of the planning process operating in New South Wales during this period, the focus throughout is on the inner western suburbs of Sydney where the most significant local opposition to the proposals emerged. When the proposals were first formulated by the Department of Main Roads in the late 1940s, ushering in the era of fixed grand plans for entire regional areas, freeways promised a safe, fast, efficient means of private travel which would provide the solution to all the city's transport needs. As Sydney underwent decentralisation in the 1950s and 1960s, however, and as car numbers rapidly increased, important questions emerged about whether freeways were appropriate forms for the urban environment. The first half of the work identifies the complex range of attitudes towards urban freeways taken by the participants in the planning process, and shows how the DMR and its proposals remained unchallenged in the state political arena until the 1970s. The second half discusses the emergence and operation of external political forces - in the form of the Whitlam labor government, the New South Wales Builders' Labourers Federation, and residents' groups - which opposed the freeways. It describes how they were able to make an impact on the state planning process and gives an account of process which led to most of the radial proposals being abandoned by the state government in 1977. The closing section gives a short review of current freeway and tollway schemes in Sydney and draws out some of the lessons of the earlier period.