The degree to which health planning and management functions are decentralised has been one of the key questions in developing countries from when they first gained independence. This paper's aim is to examine the question of the historical distribution of responsibilities within the health sector of four territories, Trinidad and Tobago, the Bahamas, Martinique, and Suriname, in order to identify the roles of the different levels, changes over time and recent reform trends, and to seek to explain the reasons for changes. These territories were selected deliberately, on the grounds of their different colonial backgrounds. Common features included identification over several decades of management structures and skills as key problems; proposals for regionalisation and greater hospital autonomy as desirable solutions; and in three of the four territories, recent implementation of major structural reforms. Important influences on the timing and nature of decentralisation reforms included political and economic factors, the attitudes of the public service unions and the medical profession, and external funders who were particularly important in financing reforms and supporting the development of detailed implementation plans. The bureaucratic inheritance of the two English-speaking countries provided major barriers to structural change, which they have addressed through reforms involving the creation of agencies with delegated authority.