This paper uses Social Contract Theory to (re) examine attempts to establish leadership roles in the East Midlands, Corby, Leicestershire and Northamptonshire between 1998 and 2015. In doing so, it makes a unique contribution to the study of place leadership by drawing on classical political theory to explore a contemporary issue in regional debate. To do this, the paper explores three stages of leadership development in the East Midlands of England, cutting across scale and place to argue that in order to establish and embed a contract with the locality leaders must take into account both the territorial and relational characteristics of their place. Where the territory had little cohesion, or did not cover a single area of economic functionality it was difficult to establish, or justify, leadership roles in those territories. In areas of economic functionality leadership required the involvement of the Local Government to demonstrate the legitimacy of the contract on offer.