The enactment of Jamaica’s independence in Kingston on 6 August 1962 did not sweep away the colonial structures that had been put in place for the previous three centuries. Constitutional change had been taking place since 1944, but unemployment and dependence on the informal sector of the economy, coupled to poor housing and slum formation, could not be put right in short order. This chapter focuses on employment/unemployment and housing issues in Kingston in the first decades after independence, and makes a direct comparison with conditions in the last years of colonialism. A major new policy introduced after sovereignty was structural adjustment, which began to be implemented in a systematic way in the 1980s, and has had a substantial—and negative—impact on the lower class. Academic opinion suggests that the Latin American and Caribbean city has been doubly undermined during the last half century: first, by massive population increase following 1950, as the balance of the population has shifted from predominantly rural to overwhelmingly urban; and, secondly, by structural adjustment, which, since the late 1970s, has undone or undermined many of the solutions to urbanization previously achieved by grassroots endeavour in the face of labour-intensive capitalism—for example, the provision of shelter through self-help housing of the squatter kind. In short, whatever benefits late twentieth-century globalization has brought to Latin American and the Caribbean, there have been massive losers among the urban poor (Clarke and Howard 1999). This chapter modifies many, but not all, of these generalizations in the case of Kingston. While its formerly protected economy has been turned inside out by structural adjustment, Jamaica’s economy, even prior to independence, was small, open, and therefore potentially vulnerable; and Kingston was already a classic example of an overcrowded metropolis with a weak industrial base. The introduction of structural adjustment in Jamaica has increased unemployment or withdrawal from the labourforce, and impacted on the housing situation among the lower class, without—in the case of Jamaica—increasing economic growth. However, in Kingston, once the immediate impact of structural adjustment was over, a static or slowly declining urban economy has gone hand in hand with a gradual reduction (so the data show) of the highest levels of unemployment and a substantial improvement in housing provision and quality, despite the fact that more than half the labourforce is in the informal sector.