21st-Century Geopolitics Of The Caribbean

The Caribbean Sea is commonly thought of as a “US lake” separating the two American continents, and it’s pretty much been under Washington’s exclusive influence since the beginning of the 20th century. Cuba is of course the exception to this state of affairs, but even that seems to be slowly changing. Although the Obama-era rapprochement with the island has been somewhat scaled back by the Trump Administration, President Raul Castro nevertheless showed his hand a couple years ago by agreeing to better ties with the US in the first place. The wisdom of that decision remains to be seen, and in hindsight, it may not have been the best idea considering that Cuba of all countries should know that the US can’t be trusted, as later events have proven with the Trump Administration. Nevertheless, the 21st-century geopolitics of the Caribbean are about a lot more than just Cuban-American relations, which is why they deserve to be studied in depth. 
The first chapter will take a look at how the Caribbean figures into China’s strategic calculus, and then explain some of the basics about this region’s geography and chokepoints. The next part will pick up where the first one left off and expand upon the geostrategic significance of the Caribbean islands-countries, ending with a brief description of the prevailing trends that are expected to unfold across the coming years. Finally, the third chapter discusses the various regional integrational organizations, while the fourth and last one ends with a forecast about how a successor state to the pre-independence West Indies Federation could realistically be created.  

China’s Strategic Thinking On The Caribbean 

The Caribbean connects the East Coast of the US with the Pacific Ocean via the Panama Canal, which accordingly also makes it the transit area for Chinese trade to and from that part of the country. This sea had a much more substantial geostrategic significance at the beginning of the 20th century than it does today, but the legacy from that period still shapes modern-day geopolitics in this region. The Caribbean Sea used to be America’s version of the “South China Sea”, in that the US had a pressing imperative to safeguard its trade and naval routes in this southern-abutting waterway much as China feels with its own southern namesake sea today. The difference, however, is that the US employed a policy of unapologetic and brutal (neo-)colonialism in order to do this, while China is aiming to cut “win-win” partnerships with all of the regional states in its neighborhood. 
Granted, the geopolitical situation is and always has been markedly different in the Caribbean Sea than in the South China Sea, whether in the early 20th century or the opening decade of the present one, but the point here is to draw attention to the comparative importance that both Great Powers place on establishing and sustaining leadership in their southern seas. The relevance in reflecting on this is that the same imperatives guiding American policy toward the Caribbean in the last century still endure in the current one, and that this could interestingly become a liability of sorts which could masterfully be exploited by China to pull a “reverse-South China Sea” against the US. What’s meant by this is that the US’ attitude to the Caribbean is similar to China’s in the South China Sea, and it’s that both Great Powers are uncomfortable with their rivals exerting any pronounced military-strategic influence in their naval underbellies. China actually has the chance to do just that in the coming decade, and it’s – as usual – proceeding silently in pursuit of this goal. 
There’s no foreseeable or realistic chance that China would exert anywhere near the military presence in the Caribbean as the US does in the South China Sea, but that’s not what Beijing is aiming for. Instead, China wants to build a new transoceanic canal in Nicaragua, closely cooperate with regional institutions, and ultimately flex its economic muscle to the extent that the Caribbean becomes a smaller scale version of Africa for the People’s Republic. The Nicaraguan Canal initiative is technically a “private” endeavor by a wealthy Chinese businessman, so there aren’t any formal policy pronouncements publicly available about the direction of this initiative, though there’s a lot of information about China’s desire to work with Caribbean institutions on the political and economic levels, which is clearly expressed through the China-CELAC Forum and China’s latest 2016 Policy Paper on Latin America and the Caribbean. 
The present research won’t dive deep into the specifics of what this entails since there aren’t any concrete New Silk Road projects that have been agreed upon other than the Nicaraguan Canal, but the primary takeaway is that the successful completion of the former coupled with the continued use of the Panama Canal will eventually lead to a surge of Chinese influence in the Caribbean so long as the present trajectory stays on course. If these comprehensive and far-sighted policies are carried out to their fullest and China is ultimately able to project its power into the Caribbean, then it would amount to an epic pivot of world-changing proportions by throwing the US on the strategic defensive in its own backyard, thereby expectedly facilitating accelerated multipolar gains elsewhere across the globe in the meantime for as long as this strategic window of opportunity remains open. 
That being said, there’s a very high chance that the US will employ Hybrid War against Nicaragua in order to disrupt, control, or influence the canal project through its mainland or maritime territory (the latter through a potential re-aggravation of the Nicaraguan-Colombian island dispute), which in that case would leave China entirely dependent on the Panama Canal for its engagement with the Caribbean states. Even so, however, it’s extremely unlikely that the US would ever act to close the Panama Canal to Chinese shipping, so it’s essentially caught in a Catch-22 of sorts which will probably lead to it uneasily monitoring the growing Chinese strategic presence in the Caribbean just as the Chinese are doing to the American one in the South China Sea. 
That’s actually what China is hoping for; to make the US feel uneasy in its own backyard and potentially encourage it to take rash actions there which end up doing more harm than good to its regional hegemonic standing. China’s track record of responses to American aggression have always been asymmetrical, so it’s natural that this will also be the case in terms of Beijing’s grand strategy towards the Caribbean. China expects that its expanding influence there will eventually sway some of the remaining 20 holdouts “recognizing” Taiwan (over half of which are in the Western Hemisphere) to recant their positions just as Panama pivotally did in mid-June 2017. The symbolism behind Panama City’s dramatic move was powerful enough that it prompted observers to question whether a domino effect of “de-recognition” was imminent. While that might not turn out to be the case anytime soon, it’s still instructive that the world was seriously considering this, and it serves as a relevant lead-in to discussing the 21st-century geopolitics of the Caribbean. 

Geographic Basics

Before going any further in carrying out the study, the reader needs to be introduced to the region’s geography:
Lucayan Archipelago: 
Although not geographically part of the Caribbean, it’s commonly grouped together with the larger region for historic-demographic reasons and consists of the Bahamas and the UK colony/”dependency” of the Turks and Caicos Islands. 
This term refers to all of the Caribbean islands, whether large or small. 
Greater Antilles:
As the name suggests, this describes the large islands of Cuba, Jamaica, Hispaniola/Haiti (original native name), and Puerto Rico/Borikén (indigenous name), as well as the much smaller British holding of the Cayman Islands for geographic purposes.
Lesser Antilles:
These are all the smaller islands of the Caribbean and are divided into three chains which comprise a combination of over 20 sovereign states and colonies/”dependencies” (also known as “overseas territories”):
* Leeward Islands
The very small islands located in the northeast of the Caribbean and bordering the Atlantic are the Leeward Islands:
- Anguilla (UK)
- Antigua and Barbuda 
- Dominica (sometimes classified as part of the Windward Islands)
- Guadeloupe (FR)
- Montserrat (UK)
- Saba (ND)
- Saint Kitts and Nevis
- Sint Eustatius (ND)
- Saint Barthélemy (FR)
- Saint Martin/Sint Maarten (island divided between FR and ND)
- Virgin Islands (US and UK)
* Windward Islands
These islands are comparatively larger than the Leeward Islands and are located to their south closer to South America:
- Dominica (sometimes classified as part of the Leeward Islands)
- Grenada 
- Martinique (FR)
- Saint Lucia 
- Saint Vincent and the Grenadines 
* Leeward Antilles 
Geographically disconnected from the Greater and Lesser Antilles chains, the Dutch “ABC” island holdings of Aruba, Bonaire, and Curaçao, and over a dozen Venezuelan islands, constitute what is referred to as the Leeward Antilles 
* Atlantic Exceptions
Barbados and the nation/islands of Trinidad and Tobago are not usually grouped together with any of the two Lesser Antilles island chains or the Leeward one due to their location, and are pretty much geographically “Atlantic” islands which nonetheless have an inseparable Caribbean historical-demographic heritage. 
Here’s what each of these island chains more or less look like on a map:
Red: Lucayan Archipelago 
Blue: Greater Antilles
Pink: Leeward Islands (Lesser Antilles)
Green: Windward Islands (Lesser Antilles)
Gold: Leeward Antilles 
Brown: Atlantic Exceptions


There are six main chokepoints in the Caribbean Sea which control access to and from the region:
Nicaraguan and Panama Canals: 
The first one isn’t completed yet and might very well end up falling victim to the US’ Hybrid War intrigue, but even so, the point is that there is at least one transoceanic access route (and perhaps eventually two) connecting the Pacific and Atlantic by means of the Caribbean Sea. Panama is rightly regarded as a stronghold of American influence in the Western Hemisphere, but Washington’s formerly dominant control over the country appears to be mildly weakening following its peaceful cessation of the canal to Panama City at the turn of the century and the latter’s recognition of Beijing in June 2017. 
Florida Strait: 
Although technically only linking the Atlantic Ocean and the Gulf of Mexico, control over the Florida Strait was an important determinant impacting American grand strategic thought on the Caribbean in the late-19th and early-20th centuries. The US gained uncontested control over the strait following the 1898 Spanish-American War and the subsequent occupation of Cuba. Afterwards, Washington was able to project its imperialist power all across the Caribbean Basin and more credibly enforce the “Monroe Doctrine” through the interlinked “Big Stick” policy, “Roosevelt Corollary”, “Dollar Diplomacy”, and resultant “Banana Wars”. 
Yucatán Channel: 
The US’ control over Cuba paired well with the weakened state that it kept Mexico in for decades to enable Washington to dominate the narrow access route connecting the Gulf of Mexico with the Caribbean Sea. This secured the energy and commercial trade routes between the (then-)prosperous northern coast of South America and the US’ regional energy and commercial centers in Houston and New Orleans, respectively.  Moreover, it also made the US the gatekeeper of Mexican-South American maritime trade across the Caribbean, further enfeebling Mexico City from a strategic standpoint. 
Windward Passage:
The narrow distance between Cuba and Haiti (or otherwise perceived of as the island of Hispaniola) forms the so-called Windward Passage, which is somewhat misnamed because it doesn’t directly connect to the Windward Islands at all. This waterway forms the quickest route linking the Panama (and possibly one day, Nicaraguan) Canal to the US’ East Coast, and it’s for this reason why the US still retains its imperial-era Guantanamo Bay holding on the southeastern coast of Cuba in order to monitor and control traffic passing through this channel. 
Mona Passage:
The last important chokepoint in the Caribbean Region is the Mona Passage between the Dominican Republic (which can also be conceptualized as the eastern coast of Hispaniola) and Puerto Rico. Not as important as the Windward Passage, it does serve a purpose when it comes to energy exports from Venezuela, of which the US is the largest consumer. Vessels moving to and from the East Coast of the US can traverse through the Mona Passage, but in recent decades, however, the Mona Passage has taken on a different significance by becoming a favorite human smuggling route for Cuban and Haitian migrants eager to make it to the US territory of Puerto Rico before finding a way to the mainland. 
Crucial Cuba:
Reflecting on the geostrategic importance of the aforementioned Caribbean chokepoints, it should become obvious why the US is so obsessed with controlling Cuba. The island nation sits at the crossroads of three separate chokepoints, and the US fears that Havana’s partners in Moscow (during the Old Cold War) and Beijing (during the New Cold War) could leverage this to their advantage in pivotally undermining Washington’s interests in its own backyard. This explains why the US has done everything that it could to prevent Cuba from exercising its sovereign right as an independent state in conducting the foreign policies that best promote its national interests, and also why it took such a hard line during the 1962 Caribbean Crisis (also known as the Cuban Missile Crisis in the West). 
To make everything easier to understand, here’s a cartographical representation of the Caribbean chokepoints:
Gold: Panama and Nicaraguan Canals
Red: Florida Straits
Green: Yucatán Channel
Blue: Windward Passage
Purple: Mona Passage