The New York metropolitan region is a geographically complex, politically fragmented and economically powerful place. To date, few formal partnerships at the regional scale have emerged, and even fewer have proved durable. Because of this, intergovernmental cooperation is vital to keeping New Yorkers moving. In order to build new transportation infrastructure, actors have engaged in an ongoing process of negotiating space, power and scale. This chapter explores scale construction (or its absence) through an analysis of six transit-oriented development projects attempted within the NY metropolitan region: the Hudson and Manhattan tunnels, the North River tunnel, the Holland and Lincoln vehicular tunnels, the George Washington Bridge, and Access to the Regions Core. Using a process of reverse engineering, we use these cases instrumentally to build an understanding of the nature scalecraft in this region, highlighting it as a dynamic and changing process rather than one which is static and unidirectional. Despite the obvious benefits of regional governance in the NY metropolitan area, these projects all reveal that the divided and competitive political system is simply not conducive to developing a regional scale. This analysis highlights the major tensions within regional transportation policy and demonstrates that the roles of key actors have remained consistent over time.