The West Indies Federation was an experiment in unity for the English Speaking Caribbean and should have resulted in an independent West Indian nation.. After long discussions it came into being in 1958. Elections took place that year but Jamaica and Trinidad did not join the new political unit with the same commitment as the other islands. Economic prosperity meant that these two islands did not feel the need to be part of a larger grouping to achieve independence. The fact that the Federation did not have a source of funds for its own use also damaged its longevity.

The end came in 1962, barely four years after it had been launched. The idea of Federation was not abandoned by the smaller islands. A Little Eight grouping with Barbados was discussed, but when that island chose to seek independence on its own, Grenada soon followed and the remainder attempted a smaller union which eventually emerged as the OECS.
For those that needed more preparation to move towards independence, the concept of Associated State with Great Britain was created. St. Kitts-Nevis-Anguilla was the first to take the new status. Under this constitution the State of St. Christopher, Nevis and Anguilla had the authority to make decisions on internal affairs while Britain retained responsibility for external affairs. The Premier now presided over Cabinet meetings and the Cabinet was collectively responsible for the actions of individual ministers in the execution of his/her work. The new state was responsible for all internal matters. That same year Anguilla chose a different destiny.