A Caribbean Diaspora has emerged worldwide after 500 years of European colonial exploitation of the Caribbean geopolitical region. This exploitation has a two-tiered social legacy: the ‘haves'; and the ‘have-nots', characterised by poor educational achievement, underdevelopment and unemployability of the many. The Caribbean Diaspora is a product of ever-increasing fantasies of escape from poverty by migration to greener ‘First World’ pastures. The complex, contradictory Caribbean society generates a crucible of misery and violence amid opulent wealth and luxury, which requires a burgeoning private and public police and military apparatus for its containment, and an ever-increasing health, mental health and penal correctional system to buttress the casualties of this conflict that is spiralling out of organisational and economic control. This two-tiered society was inherited from the hierarchical legacy of European colonialism. The colonisers existed in a system of high productivity and order, which imposed its will on the colonised, who lived in relative disorganisation and need. The resultant vector of this unequal yoke is the virtual anarchy of present-day Jamaica and other Caribbean territories, characterised by a subculture of violence and increasingly violent crime. The physical, psychological and economic costs of this seeming conundrum are bewildering and unaffordable.