As part of its decision to push modified self-government, the British authorities encouraged the experiment in confederation. The idea had been discussed in the Colonial Office since the later nineteenth century, but it was brought to new life with a regional conference held at Montego Bay, Jamaica, in 1947. The British were interested in administrative efficiency and centralization. The West Indians talked about political independence. At the conference, a compromise was worked out. The West Indian Meteorological Services and the University of the West Indies, as a College of London University, were set up, and plans were made for the creation of a political federation that would unite the various territories and eventually culminate in the political independence of the region. These new regional organizations joined others already in existence, such as the Caribbean Union of Teachers, established in 1935; the Associated Chambers of Commerce, organized in 1917; and the Caribbean Labour Congress, inaugurated in 1945.

The federation began inauspiciously with the leading politicians in Jamaica--Norman Manley (then prime minister) and Alexander Bustamante--and in Trinidad and Tobago--Eric Williams-- refusing to contest the federal elections. This uneasy federation of ten island territories (Jamaica, Trinidad and Tobago, Barbados, Grenada, St. Kitts-Nevis-Anguilla, Antigua and Barbuda, St. Lucia, St. Vincent and the Grenadines, Dominica, and Montserrat) lasted from 1957 to 1961, when Jamaica opted to leave. Doomed from the start by lukewarm popular support, the federation quickly foundered on the islands' uncompromisingly parochial interests, especially those of the principal participants, Trinidad and Tobago and Jamaica. The former would not accept unrestricted freedom of movement; the latter would not accept a binding customs union. On September 19, 1961, some 54 percent of the Jamaican electorate voted to end their participation. It was the lowest popular vote in any Jamaican election, but the government accepted the decision and initiated the plans to request complete independence for the state. Attempts by Trinidad and Tobago and Barbados to salvage the federation after the withdrawal of Jamaica failed.