Crisis in Cuba: George Friedman on the Return of US Pressure
Cuba stands at a crossroads as the Trump administration ramps up pressure on the island nation, indicting President Raúl Castro and offering Cubans a new relationship with Washington. But this isn't a new story—it's the latest chapter in a geopolitical drama stretching back to the Monroe Doctrine of the 1820s. With Cuba's economy in collapse, its army essentially a criminal cartel, and the CIA director making mysterious visits to Havana, the question looms: will the US finally resolve its 200-year-old Cuban problem? And if so, how—through economic strangulation, covert action, or outright invasion?
Key Takeaways
Cuba's strategic location—controlling the 90-mile-wide Straits of Florida through which half of US imports and exports flow—has made it a central geopolitical concern for every American president since the Monroe Doctrine.
The Cuban government is no longer ideological but essentially a criminal enterprise: the army controls the country, enriches itself through cartel partnerships, and maintains order through force rather than popular support.
The US strategy is economic strangulation and covert pressure rather than invasion—allowing Cuba's catastrophic economic collapse to potentially trigger internal uprising or regime fracture without the cost of ground war.
The real threat isn't Cuba itself, but the possibility that a hostile foreign power—historically Spain and the Soviet Union, potentially China in the future—could use the island as a base to threaten US interests.
Trump has learned from Iran that even overwhelming US military power faces limits in specific situations, making him cautious about committing to a Cuban invasion despite the island's strategic importance.
In a Nutshell
The US views Cuba not as a direct military threat, but as a dangerous vulnerability—a strategically located island that foreign powers could exploit to threaten American sea lanes and Gulf Coast trade. Trump's strategy appears to be economic pressure and covert destabilization rather than invasion, banking on internal collapse rather than costly military intervention.
Two Centuries of American Obsession
Cuba has dominated US strategic thinking since the 1820s Monroe Doctrine.
The US-Cuba relationship stretches far beyond the Cold War imagery of Castro and the Bay of Pigs. From the early 19th century, Cuba occupied American strategic thinking—the Monroe Doctrine was issued largely with Cuba in mind, as Washington distrusted Spanish control of an island so close to its shores. The US offered to purchase Cuba from Spain, and when that failed, fought the Spanish-American War in 1898 partly to seize it. Theodore Roosevelt's famous charge up San Juan Hill took place in Cuba, not on the American mainland.
After winning the war, serious discussion occurred about making Cuba a US state. Instead, it became a quasi-protectorate until the Castro revolution. The fundamental geographic reality never changed: the Straits of Florida, just 90 miles wide between Key West and Cuba, channel roughly half of all US imports and exports from the Gulf Coast. Any hostile power controlling Cuba could potentially block this vital artery. This fear drove US policy through Spanish control, the Soviet alliance, and now the cartel-linked military regime.
The Cuban Missile Crisis nearly triggered nuclear war precisely because the Soviets attempted to base nuclear weapons on the island. When the Soviet Union collapsed, Cuba lost its patron and its economy began a decline that has accelerated into the current catastrophic conditions. Yet the strategic geography remains unchanged, and with it, Washington's concern about who controls the island and what foreign powers might use it as a base of operations against American interests.
The Army as Criminal Enterprise
Cuba's government is no longer ideological but a cartel-linked military organization.
The Army as Criminal Enterprise
Cuba has evolved far from Fidel Castro's revolutionary ideals. Today, there is no government of Cuba but the Cuban army—no longer ideological but essentially a criminal organization. The military controls the country through domination and enriches itself through partnerships with drug cartels operating throughout the region. This is why Cuban forces, not Venezuelan troops, protected Maduro when US Delta Force operators moved against him. The army lives well while ordinary Cubans face starvation, blackouts, and third-world conditions.
Why Islands Matter in Geopolitics
The CIA Director's Mysterious Visit
An operational intelligence chief in Havana signals deep penetration and covert options.
The CIA director's recent visit to Cuba defies normal diplomatic protocol—intelligence chiefs don't typically conduct open negotiations with foreign governments. Friedman speculates this was a calculated signal rather than traditional diplomacy. The director, an operational officer rather than a diplomat, may have been demonstrating just how deeply US intelligence has penetrated Cuban operations, assets, and cartel relationships.
The message would be clear: Cuba won't be fighting the conventional US Army but rather a covert force that knows everything about their operations, locations, and vulnerabilities. This represents a different kind of pressure than economic sanctions or public indictments. It's psychological warfare aimed at the military leadership, letting them know that nothing they do is invisible to American intelligence. The hope would be that this knowledge, combined with economic collapse, might fracture the army's cohesion or willingness to resist regime change without the US firing a shot.
Strategic Options and Constraints
Washington prefers economic collapse and internal uprising over costly invasion.
Economic Strangulation Continue blocking oil access and tightening sanctions, allowing Cuba's already catastrophic economic conditions to worsen until even the army's position becomes untenable.
Covert Destabilization Use CIA assets to support internal uprising, leveraging deep intelligence penetration to weaken military cohesion and enable Cubans themselves to overthrow the regime.
Symbolic Pressure Indict aging leaders like 94-year-old Raúl Castro, issue video addresses to the Cuban public, and demonstrate willingness to prosecute regime figures—building psychological pressure without military commitment.
Military Invasion (Last Resort) Direct military action remains possible but undesirable—Cuba is large, the army could fight effectively despite being mercenary in nature, and Trump has learned from Iran that US power has limits in specific situations.
The Real Threat: Foreign Occupation, Not Cuba Itself
Cuba's weakness makes it vulnerable to exploitation by hostile great powers.
Cuba's Catastrophic Reality
The economy has collapsed into third-world conditions with mass suffering.
What History Says About Cuba's Future
Friedman sees internal collapse more likely than US invasion.
“The more pressure we put on them both in terms of access to oil, their economy, and everything else, the weaker they become. The weaker they become and the worse the standard of living is in Cuba. Well, the army is a very powerful tool against civilians. They may or may not rise up. They may rise up with American help. So, there are a number of options the Americans can take. One is covert, sending CIA to have an uprising. The other is to strike militarily. And the other is simply to stand back and let them sweat it out if they can and likely go down in long term.”
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