Excerpt from Douglas Oswald’s “Annotated History of the American Revolution”, University of Michigan Press, 1932.
At the onset of the revolution, the legal status of much of the British Caribbean was suddenly thrown into considerable doubt. Before the war the British Caribbean was a hodgepodge of tropical outposts designed to gather resources (normally sugar but sometimes tropical lumbers) and counter France or Spain. For example the majority of British commerce centered on the incredibly profitable sugar plantations of the Leeward Islands and Jamaica. British outposts off the coast of Central America gathered lumber and hindered the Spanish. The Cayman Islands and the Bahamas were good strategic outposts but their sandy islets and shallow cays prevented the dominant sugar economy from, quite literally, taking root.
In addition, the nature of the Caribbean meant that control of the islands themselves was tenuous at best. Many islands were swapped back and forth between Britain and other European powers during the constant outbreak of wars that occurred from the 16th century until the American Revolution. Several islands (Dominica, Grenada, and St. Vincent) were eager to join the American cause as they had been recently conquered during the French and Indian War and had sympathetic French populations. In addition, the Caribbean islands were especially vulnerable to slave uprisings, disease, hurricanes, and piracy, which made their situations extremely unstable. This led to a continuous parade of colonial governors sent from London and constant reorganizations in an attempt to manage the ever changing mess. At the time of the Revolution, the Cayman Islands and British holdings and protectorates in Central America were administered from Jamaica. Anguilla was administered from Antigua and Antigua itself was administered as part of the British Leeward Islands which itself was divided into northern and southern groupings.
Lastly, by the time of the Revolution the settled white population of townsfolk, overseers, and resident plantation owners were at odds with incompetent colonial administrators and landowners who were happy to manage their estates from Britain via proxies. This cultural divide combined with the uncertainty of the situation on the mainland made the Caribbean ripe for joining the revolutionary cause which is exactly what happened over the course of 1775 and 1776. Simply put, the pent up animosity and potential for economic gain by keeping profits at home instead of shipping them back to Britain outweighed the tenuous strategic position of the various islands allowing rebellion to foment.
While Commodore William Briggs made his legend known countering the mighty Royal Navy and keeping the Caribbean as safe as he could, the legal complexities of the region continued to unfold. At first, as the islands began to throw off colonial yokes, they organized based on territory itself. The Second Continental Congress saw delegations arrive from the individual islands themselves. The only British North American territories to not be represented in Philadelphia were the Central American outposts, East and West Florida, and the vast Hudson’s Bay Company holdings in Canada. The delegations to the Congress actually worked together quite well even if the authority they acted upon was questionable. Many of the smaller islands had unique free populations, all dwarfed by massive slave populations, and only a handful had pre-established colonial assemblies. Many islands had to create assemblies from scratch to vote on delegates. Sometimes this occurred with the actual formation of a new assembly as was the case in St. Christopher  and the Bahamas. On the smaller islands the assembly was little more than a majority of free landowners meeting at a church. Anguilla has no record of a colonial assembly meeting to discuss the revolution at all, this despite sending (allegedly) a representative to the Congress!
As the revolution played out the legalities and politics of the era spilled into the Caribbean. Assemblies in the Bahamas, Barbados, St. Vincent, and Grenada were all interrupted by British occupation. Several leading politicians, including John Adams, doubted the patriotic loyalties of several islands that had only recently become British. In a famous spat while the Congress executed its work under great stress while exiled in Fredrick, Henry Perdue of Dominica called Roger Sherman of Connecticut an adulterer to which he retorted that Perdue was nothing more than a “French parasite”. In the meantime, the local assemblies and governments began to understand where their British overlords had been coming from all those years when they tried to coordinate war efforts themselves. It was with much humility that several islands realized their small populations and isolation were stronger united than apart. In 1778 the Cayman Islands and Jamaica agreed to merge and to this day the Cayman Islands remains a county of Jamaica. In 1779, Antigua, Barbuda, Anguilla, Montserrat, St. Christopher, and Nevis all merged to form the Leeward Islands. To make matters more confusing, St. Christopher and Nevis would go on to secede from the Leeward Islands during the Civil War, opting to form their own neutral state which remains separate to this day. Early discussions for a merger between Dominica, Grenada, St. Vincent and Barbados were held but the subsequent British occupation derailed these plans. Talks briefly resumed after the war ended but the cultural gap between French Dominica, Grenada, and St. Vincent and British Barbados brought these to a halt. The Dominica Crisis of 1782 stemmed from this organizational failure but set the United States up for far greater achievements.
: St. Christopher being the old name for modern day St. Kitts.