How urban economies evolve has a rich literature. The impulse to discern longitudinal patterns of development can be seen in the body of work on path dependence. However, it has been noted that the drivers of path dependence are under-specified. In this paper we seek to make an association between real estate development in England and the longer term path dependence that has bequeathed an extremely geographically unequally pattern of economic development. In so doing we present empirical research from a major study of ‘developer contributions’ that associates behavioural aspects of the planning process through which developer contributions are determined and the creation of virtuous/vicious circles of development. It is our contention that these virtuous and vicious circles represent an important but under-researched aspect of the highly varied path dependencies observed in settings such as England that we describe here as poverty and affluence traps.