This dissertation aims to work at the intersection of political theory and policy while it considers the interaction between technology and democratic practices located in disputes regarding the construction of urban interstate freeways in the Twin Cities of Minneapolis and St. Paul, Minnesota. Although many issues, ranging from the safety of toys to complex matters regarding health care, are considered appropriate arenas for citizen participation, transportation remains largely in the realm of decision making handled by professionals removed from interaction with citizens. Although this claim to privilege via apolitical expertise persists, decades of dissonance have unmasked it and dramatically modified its effects. As we face the realities of global warming, the tensions surrounding the relationship between technical experts and citizens will only become more significant because road transport accounts for 25 percent of global carbon dioxide emissions. The politics surrounding urban interstates is one of many areas in American life in which it is clear that democracy and the requirements of complex technologies are ill-suited for each other, yet they are inextricably bound. The discussion in this paper is based on consideration of seven cases of citizen protest of interstate construction through urban areas. Analysis is structured around three eras which reflect a dramatic change in the expectations of the public regarding interstates as they relate to the environment, the citizenry's articulation of its vision and values via direct participation and through elected representatives, and the adaptation by experts and institutions. Incipient forms of deliberative democratic political practices broke through a previously exclusionary bureaucracy via the citizen protests of urban interstates in Minneapolis and St. Paul in the two decades from 1970 to 1990. For a complex array of reasons, including greater competition among scarce resources, anti-tax sentiments, and a vague disillusionment with government, public support for transportation investments waned after this period even as the costs continued to increase dramatically. While citizens had moved further into the design process, opening new possibilities for transportation politics, further development of structures for meaningful citizen engagement was halted due to lack of funds, lack of commitment, and lack of vision.