Colonial period 1627–1816 Under the
Carlisle proprietorship of 1627,
Barbados and the Leewards were grouped together. In practice, this arrangement was difficult to administer, and
Thomas Warner governed the Leeward Islands only. In 1660
Lord Willoughby, as Governor of Barbados, also governed all of the Eastern Caribbean, then under English rule. This scheme was approved by the Leewards as they needed the military aid of Barbados at the time during the
Second Anglo-Dutch War. Otherwise, the planters on the Leewards competed with those in Barbados as rivals for the greatest share of the
sugar trade with England. After the war, England gave in to the demands of the Leewards for a separate government. In 1671, the Crown assigned a governor-in-chief to manage
St. Kitts,
Nevis,
Anguilla,
Montserrat,
Antigua and
Barbuda.
Sir William Stapleton established the first federation in the BWI in 1674. Stapleton set up a General Assembly of the Leewards in St. Kitts. Antigua, Montserrat, Nevis and St. Kitts sent two representatives each. One governor had responsibility for the Leewards and a lieutenant governor was appointed for each island. Stapleton's Federation was active from 1674 to 1685, during his term as governor; the General Assembly met regularly until 1711. Afterwards, it only met once more in 1798. The federation was unpopular, and in 1683 the islands rejected a government proposal for one government and set of laws. By the 18th century, each island had kept its assembly and made its laws, but continued to share one governor and one attorney-general. Although unpopular, Stapleton's Federation was never really dissolved but was simply replaced by other arrangements.
Colonial period 1816–1869 Between 1816 and 1833 the Leewards were divided into two groups, each with its governor: St. Christopher-Nevis-Anguilla and Antigua-Barbuda-Montserrat (including Redonda). In 1833, all the Leewards were brought together again under the pre-1816 and
Dominica was added to the grouping until 1940. In 1869, Governor Benjamin Pine was assigned to organize a federation of Antigua-Barbuda, Dominica, Montserrat, Nevis, St. Kitts, Anguilla, and the
British Virgin Islands. St. Kitts and Nevis, however, opposed sharing their government funds with Antigua and Montserrat, which were bankrupt. Governor Pine told the
Colonial Office that the scheme had failed due to "local prejudice and self-interest". Thus the only achievement was giving the Leewards a single governor. All laws and ordinances, however, had to be approved by each island council.
Federal colony 1871–1956 In 1871, the British government passed the
Leeward Islands Act through which all the islands were under one governor and one set of laws. Each island was called "
Presidency" under its administrator or commissioner. Like earlier groupings, this federation was unpopular but was not dissolved until 1956 to make way for the Federation of the West Indies. The Federal Colony was composed of all islands organized under Governor Pine's previous attempt. == Windward Islands ==