Colonial-era administrative institutions and doctrines are fundamental to any analysis of Westminster's legacy in the Caribbean. Applying the lens of ‘Public Service Bargains’ (PSBs) – the formal and informal understandings of reward, competence and loyalty of public servants – we first examine constitutional and administrative doctrines regarding the public service of Crown Colonies, before analysing how these worked themselves out in Jamaica. Our analysis reveals a number of perceived deficiencies in the PSB in the pre-independence period that cast a shadow on future relations in the post-independence period.