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The Central Artery/Tunnel (CA/T) project in Boston is the most expensive highway project in the history of the United States and it is being built in the heart of a region that was at the forefront of the anti-highway movement in the late 1960s and early 1970s. This case examines how the more than $5 billion project came about, with a particular focus on several controversies that beset the carefully designed project in late 1990, as its proponents tried to obtain required state and federal environmental permits. The epilogue discusses how a lame-duck administration tried to resolve these disputes before it left office and how these efforts created a host of new controversies for an incoming administration that in general was the ideological opposite of its predecessors. The case allows students of transportation, urban politics and economics, and of politics generally to consider the political strategies necessary to move major projects from conception to construction and to analyze whether those strategies produce benefits commensurate with their costs.