Thanks to the riches to be had in spices, sugar, bananas, and rum, the Caribbean was the site of near-constant warfare, piracy, and flag-exchanging, and some islands changed hands many times over the 19^thcentury.  Spain named many of the islands and groups thereof, including Trinidad, the Bahamas, and Jamaica, while France retained some of the most economically important sites in the region, but control over the bulk of the archipelago ultimately settled in British hands.  One wouldn’t know it from the place names, but the United Kingdom was the overwhelming winner of the Caribbean conqueror’s game.  The latecomers to the Age of Imperialism, such as Sweden and Latvia, didn’t stand a chance.

Whatever the history of conquest, Britain did not settle the Caribbean the way it settled the North American mainland.  Each island territory was run primarily as a business venture, and only a small number of Britons made their homes there.  Instead, the islands were populated with thousands of African slaves and Irish indentured servants (not slaves, despite similar living conditions) and, after the abolition of slavery in the British Empire, indentured servants from India.  Indigenous Caribs and Arawaks, on the islands that had such populations, were enslaved, exterminated, or forced to flee, and persist mainly as isolated pockets on a few islands and as part of Belize’s Garifuna community.  In their absence, the black inhabitants of the various islands in particular found themselves in an interesting position.

The slave populations of the Caribbean were taken from throughout Britain’s highly multiethnic West African colonies.  In most cases, English was a necessary intermediary language, enabling speakers of Yoruba, Igbo, Hausa, Fulani, and other highly dissimilar Niger-Congo and Afro-Asiatic languages to communicate with one another.  This isolation from their distant homelands, forced proximity to one another, and externally imposed language and culture led the Afro-Caribbean populations to become a distinct ethnicity all their own, much like African-Americans.  Creole languages developed on most of the islands, with English continuing to serve as a lingua franca.  This gives the Caribbean islands, and similarly settled mainland sites such as Belize, Guyana, and Suriname, a particularly unusual postcolonial narrative.  The islands, collectively, retain only a tiny fraction of their original Carib and Arawak inhabitants, and most of their populations came from elsewhere in the world.  Yet they do not fit the “settler state” narrative that defines the US, Canada, Australia, and New Zealand, and this shows in the manner of their subsequent development.  In a sense, the Afro-Caribbean and Indo-Caribbean islanders are “new indigenous,” populations quite distinctive to their Neotropical homes but nonetheless not “original” to them.

The nature of the colonial regimes in the Caribbean cements the comparison to Africa rather than to the settler states.  Perhaps even more so than the United States and Canada, the people of the Caribbean islands were under unfair economic and social arrangements with their colonial power.  Britain ended slavery in its lands long before the United States did, but its attitude toward its Caribbean colonies remained essentially exploitative, much like its attitude toward similarly situated Newfoundland and Bermuda.  Institutional racism held down the aspirations of the vast majority of the islands’ inhabitants.  Before the establishment of the regional assemblies of Jamaica and its dependencies, the British Windward Islands, and the British Leeward Islands, the colonies were run in an exaggerated version of the same non-representative government that partly incited the American Revolution.

The Caribbean islands faced a difficulty that the much larger and more ecologically diverse United States and Canada did not, however.  Most of them were conceived as little more than facilities for extracting a single resource for export, like Britain’s African colonies.  The United States and Canada had burgeoning populations with growing manufacturing and other sectors and land to spare, but the Caribbean islands were, for the most part, intensive monocultures of spices, bananas, sugarcane, salt, and similar commodities with little room for diversification.  Since the islands received whatever industrial products they required from elsewhere in the British Empire, there was no incentive to cultivate such industries on-site.  Likewise, since the Caribbean spent most of its colonial history not as a place where people lived (despite its millions of people), but where they worked, it was short on educational institutions and other paths to an educated governing class.  This dependence made the prospect of breaking free of Britain difficult to sustain until nearly 200 years after the United States’s independence and 100 after Canadian confederation.

In an intentional mirror to the Canadian and American unifications that made those countries the nigh-instant successes that they were, in 1958 Britain attempted to organize most of the British Caribbean territories into a single large entity.  This West Indies Federation combined the existing territories of Jamaica and its dependencies, the British Windward Islands, and the British Leeward Islands under a single overarching government, while breaking up those older groups.  Other possessions, such as the Bahamas, Belize, British Virgin Islands, and Guyana, either saw their future in association with other nearby states or had too much internal strife to consider a union at the time. Thus, Jamaica (with the Cayman and Turks and Caicos Islands), Montserrat, Antigua and Barbuda, St-Kitts-Nevis-Anguilla, Dominica, St. Lucia, St. Vincent and the Grenadines, Barbados, and Trinidad and Tobago entered the Federation as separate, nominally equal constituent parts.  And that’s where the trouble began.

But that was trivial compared to the Federation’s internal politics.  A truism about federations is that they begin to self-destruct when individual constituents are powerful enough that they don’t need their fellows, but their fellows need them.  The West Indies Federation consisted of three large, populous, increasingly wealthy parts—Jamaica, Barbados, and Trinidad and Tobago—and a whole series of smaller, weaker entities.  Most of those smaller entities were already riven with divisions, usually related to smaller islands (such as Nevis and Barbuda) complaining of neglect by their larger government seats (St. Kitts and Antigua, in this case).  The creation of an overarching Federation did nothing to assist with this problem, nor did it dampen the rivalry that many of these island nations, accustomed to competing with one another like businesses, felt for one another.  Such was the fear that the economies of the larger islands would overwhelm the smaller that the West Indies Federation was not a single customs union, and commerce between islands required tariffs and duties.  Likewise, movement between islands was not as free as one would expect within a single country, in an effort to prevent the population of the smaller islands from fleeing en masse to the larger ones.

This internal wariness played out in a much more overt manner in the federal budget.  The Federation’s overall budget was quite small, limiting the Federation’s reach even in the matters over which it was to have sole jurisdiction.  Jamaica and Trinidad provided 85% of it and faced constant calls from the other islands to contribute more, building resentment among their populations.  Jamaica in particular rapidly grew hostile to the idea of the Federation, since it was severely underrepresented in the Federation’s parliament and was snubbed as the site of the Federation’s capital in favor of Trinidad.

In the end, this resentment led Jamaica and then Trinidad and Tobago to leave the Federation, and it collapsed altogether four years after its founding.  Most of its constituents became independent countries within a decade of that collapse, spending the interim as separate British possessions.  A few—the Cayman Islands, the Turks and Caicos, Montserrat, and Anguilla—separated from their parent colonies to become separate British overseas territories, status that they currently retain.

Despite the failure of the political union, the common culture and language across the former and current British West Indies make the prospect of future ties strong.  In particular, the islands’ pursuit of tourism, financial services, light manufacturing, and oil exploration has lifted most of their fortunes considerably compared to what they were in the late 1950s.  While most of them still face economic challenges that keep them much less developed than Canada and the United States, and sometimes even than Colombia and Venezuela, all are significantly better off and less of a burden on a hypothetical new federation than they might have been the first time around.  Conversely, Jamaica has enough problems of its own that it is unlikely to intentionally involve itself in any union that the former British Windward and Leeward Islands might attempt.

Another important variable is the existing web of supranational organizations that covers the Caribbean.  The most important of these is the Caribbean Community, or CARICOM.  Based in a now-independent Guyana, this organization includes most of the English-speaking Caribbean islands and has some input from neighbors of other languages.  Like the European Union, CARICOM has already implemented a single market, common passport, and common stock exchange for various combinations of its members, and has plans for a currency union, greater freedom of movement, and other unifying efforts.  Since much of the eastern Caribbean already uses the shared East Caribbean Dollar as its currency and the entire region pegs its currency to or flat-out uses the US dollar, a currency union would be less difficult to implement here than it was in Europe.  CARICOM includes discussions of political mergers between its member states, keeping that possibility alive.

Guyana’s role as the center of CARICOM makes the question of future political unions particularly interesting.  Despite being on South America’s North Atlantic coast, Guyana is culturally part of the British Caribbean, differing mainly in that it has unusually high indigenous and Indian populations compared to most of the island states.  While small by South American standards, Guyana’s size compared to the Caribbean island nations, similar culture, geographic proximity, and role as the seat of their unifying organization make it a natural choice to form the core of a new Caribbean federation.  The resources available to develop and improve the smaller Caribbean islands, such as Grenada and St. Lucia, would massively increase with such a union, while the diversity of economic activity across the new nation would keep it safer from recessions and vagaries of sugar, nutmeg, and banana sales that currently hamper the region’s development.