Drawing on the history of four independent transportation agencies, this essay suggests models for place-based systems that promote urban mobility. It accounts for the adversarial relationship between contemporary champions of automobile-oriented infrastructure and mass transit advocates by tracing the political and institutional history of passenger transport in America. It also points out several significant exceptions to the overall pattern of modal separation and competition, describing how revenue from bridges and tunnels in New York City and the San Francisco Bay Area was harnessed to finance and support complementary mass transit. The author notes how tolls and fees paid by drivers subsidized transit that reduced traffic congestion and supported urban vitality. Observing that regime change and economic stimulus spending now presents a rare window of opportunity for change, the author calls for reconceptualizing policy and reconstructing institutions to support efficient, equitable transportation systems that transcend modes and promote sustainable urban development.