Caribbean Cold War: Great Man Theory
- cepmurphywrites
- Sep 5
- 9 min read
By Gary Oswald.

This is the eighth article in the Caribbean Cold War series and in the previous seven, Fidel Castro, the Cuban dictator, has been a prominent figure as an inspiration and a warning, somebody who radicals and conservatives alike used as justification for their actions. But in none of the incidents I talk about does Castro himself really do much. He lent some aid to the Grenadian communist government, offered a loan to Cheddi Jagan that was turned down, and armed some, largely useless, rebels operating in Haiti and the Dominican Republic but, within the events I talk about, his reputation vastly outstrips his actual actions in terms of impact.
That isn't really an accurate representation of one of the most important figures in Caribbean history. There is a reason why Eric Williams' history of the region is called From Columbus to Castro. The man was a big deal.
Castro is a deeply controversial figure, who different people view as either an angel or a devil and whom it is hard to nail down all the facts about. Even as something as simple as 'when did he become a communist?' is impossible to answer. During the Cuban Revolution he repeatedly denied being a communist, despite his brother Raul being one, and described himself simply as a nationalist. After forming an alliance with the USSR, he declared however that he had always been a communist in his heart. Was he? Had he been radicalised, was this a pragmatic man lying, or had he always been a secret communist? It's impossible to know, but lots of people are happy to assume they do.
When talking about his legacy, let us start with the undeniable truth that Castro's Cuba was an undemocratic state with very little freedom of expression of any kind, and which would lock up dissidents in insane asylums for saying things that disagreed with the regime line. Arbitrary arrests, forced labour, torture, and summary executions are relatively well documented. Moreover, the Cuban state remained deeply racist and homophobic with Afro-Cubans disproportionately punished and disproportionately liable for the draft and gay people targeted with public humiliation and imprisonment in labour camps.
Having said that, it is very rare for Latin American dictators to actually achieve things and Castro did. Partly this is because he inherited a country in an incredibly bad position, thanks to the corrupt and brutal dictator he overthrew, Fulgencio Batista, who had sold the country to foreign interests.
By the late 1950s, U.S. financial interests owned 90% of Cuban mines, 80% of its public utilities, 50% of its railways, 40% of its sugar production, and 25% of its bank deposits—some $1 billion in total. With the doors open, American crime families like the Mafia used Cuba as a base. They funnelled dirty money into Cuba to build casinos and hotels, hoping to create a criminal empire outside the United States where they had influence over local politics but could not be affected by U.S. law enforcement. This environment, where an oppressive brutal dictator armed with US guns was selling his country's economy to American criminals, meant that there was a lot of room for improvement.
And Castro did take advantage of that to actually make things better. There is a reason why anti-revolutionary forces in Cuba had so little luck and that is because he was genuinely very popular among the Cuban peasantry. Living standards unambiguously improved under him, in terms of education, healthcare, infrastructure, land ownership, and a reduction in extreme poverty. The average Cuban is still poor (though how much of that is the fault of the government versus the embargo by the USA is debatable) but they are doing a lot better than neighbouring Haiti. He also did reform to some limited extent, for example homosexuality was decriminalised in the late 1970s.
Now personally, I expect more from my governments than just being no more brutal than the last guy. Being better that Batista is a low bar and any undemocratic state with very little freedom of expression of any kind and a history of arbitrary arrests and summary executions has serious room for improvement, regardless of the economy. But you do not stay in government for decades while sending most of your army on foreign adventures without genuine popularity, and any serious look at Cuba must account for why that exists.
Because not only was Castro a rare Latin American dictator who actually made the trains run on time, he was a rare self-declared anti-imperialist who actually was a hindrance to imperialism or at least an ally to newly independent countries. Cuban doctors and medical advisors were sent all over the Global South, and so without that numerous countries in Polynesia, Africa, and Latin America have less access to medicine. This certainly can be critiqued in moral grounds in terms of those medical workers being drafted by the Cuban government and having little choice in their destination, but it unambiguously saved lives. Likewise Cuban soldiers and military advisors were sent to the Third World in their hundreds of thousands, where they fought in many wars, often decisively. Regimes such as Apartheid South Africa and Siad Barre's Somalia probably fell sooner because of that intervention, whereas other regimes such as MPLA in Angola, the DERG in Ethiopia, or the Chávez/Maduro Regime in Venezuela were propped up. Again, morally this is a mixed bag, but in terms of sheer influence it is striking.
Cuban military intervention in Africa was often seen as directed by Moscow but government papers have indicated that it was largely a personal decision by the Cuban Government to invest in these missions. It was not something that another Soviet satellite state would have done instead. A world where Castro does not rule Cuba is a world where in all likelihood there is a lot less communist soldiers fighting in Africa.
This means a lot of things, I'll quickly run through some of the big ones:
There are no reinforcements coming to help Algeria in the Sand War against Morocco, so Hassan II possibly makes another offensive against Tindouf rather than accepting peace.
The Somali attack on Ethiopia might well be successful without Cuban reinforcements, which would mean the Ogaden joins Somalia.
As a result of that, the Eritrean Liberation Front could defeat Ethiopia during the Ogaden War, meaning Eritrea gains independence earlier and with Afwerki's more radical Peoples Liberation Front still side-lined, as they only rose to prominence in OTL because the Eritrean Liberation Front had lost to a Cuban-Ethiopian force. This might mean Ahmed Mohammed Nasser is the first leader of Eritrea instead of Isaias Afwerki.
With these major losses, the Ethiopian government under Mengistu Haile Mariam probably collapses earlier, though I'm unsure what would replace it. Probably not a monarchist restoration but the Tigray People's Liberation Front is still in its infancy at this point.
In Angola, without Cuban support UNITA have a much bigger chance of winning the Angolan Civil War; and without fighting Cuban soldiers in the Border War, Apartheid South Africa has less motive to push for peace. That probably means the regime lingers for a few more years and it certainly delays the independence of Namibia, which was only offered in return for the Cubans leaving Angola.
That is far from a complete or detailed look at the effect of a no-Castro scenario in Africa, but just that outline shows how influential the Castro regime was. Normally the POD's I talk about in this series effect only the country in question. It mattered to the people of Granada, Guyana, and Dominica who ruled them, but the outside world wouldn't be changed much at all. This isn't true with Castro. You have to go back to Dessalines and the role the Haitian Revolutionaries had in ending the Atlantic Slave Trade to find a Caribbean leader with such global influence and even across of all Latin America, there's few figures whose removal has such drastic effects.
For a start, we haven't talked about the most dramatic moment to come from the Cuban Revolution, the Cuban Missile Crisis. That crisis, over secret attempts of the USSR to put nuclear missiles in Cuba, is probably the moment where the world has come the closest to nuclear holocaust, with Castro himself writing a letter to Nikita Khrushchev telling him to launch a nuclear strike. Without a communist state in Cuba, this event doesn't happen and so the diplomatic results of that crisis, in terms of the removal of American nuclear missiles from Turkey and the establishment of the Moscow-Washington hotline, also don't happen. This might mean that a later nuclear scare goes worse as the tools aren't in place for the sides to back down.
In terms of that great power politics, both USSR and USA are very differently politically without a communist Cuba. The right-wing Cuban exiles have had an oversized influence on American politics and played a major role in the CIA's operations in Latin America. American Cold War politics were not created in reaction to Castro, Eisenhower had already overthrown the socialist government in Guatemala before this, but his presence certainly fuelled it and effected how they treat over Caribbean governments. Even American Organised Crime is very different if they don't get kicked out of Cuba and lose so much money as a result. And in the USSR, no Cuban Missile Crisis probably means Khrushchev gets a stay of execution.
So having argued that Castro was a hugely influential figure, both in the Caribbean and throughout the world, how likely is it for him to not come to power?
The Marxist argument would be that given the brutality of Batista, there would always be rebels against that. And given the obvious unfairness of the foreign domination of the Cuban economy, any successful rebel would need to nationalise those industries and redistribute land to gain support and that inevitably would mean they'd lean Marxist. In the Cold War era, they'd be unable to gain US support as a result and so would inevitably have to turn to the Soviet Union for protection. Thus if there wasn't a Castro, there'd be a Castro like figure who'd do the same sort of thing.
This, I think, is incomplete. The Cuban level of commitment to foreign conflicts is so rare among other countries of comparable size and influence that it is hard to write that off as inevitable result of any left leaning government rather than a particular quirk of a government highly influenced by figures like Castro and Guevara who had fought in foreign wars (Castro had volunteered to fight in the Dominican Republic against Trujillo).
And I think it is worth considering exactly how Castro won his war against Batista. Because he didn't win any truly decisive battles, he never had any more than a few hundred men in arms at any time. He just held on, staying alive even in moments early on in the revolution where he lost encounters badly. By the end of the war, the rebels certainly began to see victories, at La Plata, at Guisa, and most notably at Santa Clara where the rebels derailed a train bringing reinforcements to the city, but they were relatively minor encounters. The vast majority of the government’s army was intact. What Santa Clara showed was a lack of cohesion and desire to fight from the government's forces. Troops lost even when they had a large advantage in numbers and equipment because they had no will to fight, they instead surrendered quickly or fled. That is why ultimately the rebels won, because Batista simply didn't have the support of the population and as a result lost faith in his army and so fled the country long before he was defeated militarily.
Castro didn't win a conventional war, Batista's regime was just too unpopular and so couldn't survive the existence of a serious alternative. That probably would happen regardless but Castro being the universally accepted person to invite in to take control is much less certain. The early days of his guerrilla campaign were fundamentally unsuccessful, he only gained as much notoriety as he did because he lied to journalists (marching the same eight guys repeatedly past gullible cameramen to show how many men he had) and it suited both the government and the rebels to play up their threat. This became a self-perpetuating prophecy but in those early days, it's entirely possible for Castro and his men to just be killed in one of those early battles, before the turning point at La Plata.
In which case some other Cuban notable, whether that's the Catholic progressive student José Antonio Echeverría, Batista's General Eulogio Cantillo, or even Carlos Prío, the former Cuban President who had helped fund Castro, becomes the next president instead. In all those cases, it's very likely that the world will be very, very different.
Gary Oswald is the editor of the Grapeshot and Guillotines, Emerald Isles, and If We'd Just Got That Penalty anthologies.




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