The contemporary trend of connecting airports and their surrounding regions with rail infrastructure is examined through a research case study of the recent extension of the Bay Area Rapid Transit BART) system to the San Francisco Airport SFO). These air-rail links represent the latest round of civic boosterism intending to competitively position cities within the global economy through transportation infrastructure investments. This case research examines one of the key tensions in contemporary planning: how to balance the provision of effective infrastructure for urban activity and growth while preserving the quality of life and the sustainability of places. As an attempt to better connect the regional transit system with the regions primary airport, the extension project represents the regions biggest single transit investment since the completion of the original BART system in the early 1970s. A mixed methods approach is utilized in assembling the evidence. Research methods include a review of historical documents and the existing secondary literature, an analysis of primary planning documents involved in the project, interviews with relevant officials, and a quantitative analysis of collected performance data. In examining the complex evolution of the 35-year planning process of building the BART extension to San Francisco Airport, several narratives of evaluation are assembled: 1) the historical context of the involved institutions and their inter-relationshipsï¼› 2) the tension between technically grounded decision-making and decisions based upon symbolic politicsï¼› and 3) the implications of an increasingly complicated planning process within multi-jurisdictional environments. Precisely because transportation infrastructure is durable and capital-intensive, the history of institutional decision-making regarding airports, transit networks, and other facilities is primary to an understanding of contemporary policy. Due to its strong promotional appeal, the symbolism of urban design plays a crucial role, and contemporary transportation projects must also be interpreted in this light. Decisions based upon symbolic politics greatly affected the functional integrity of the project and led to significant cost escalations. In particular, the decision to extend the BART system to the airports international terminal proved to be especially costly and resulted in an inefficient functional design.