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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?

Geopolitical FuturesPolitics8 People mentioned4 Glossary terms
Video length: 32:26·Published May 22, 2026·Video language: English
7–8 min read·4,670 spoken wordssummarized to 1,409 words (3x)·

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Key Takeaways

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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.

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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.

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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.

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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.

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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.


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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.


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The Army as Criminal Enterprise

Cuba's government is no longer ideological but a cartel-linked military organization.

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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.


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Why Islands Matter in Geopolitics

🇬🇧
Britain and Ireland
England fought extended wars over Ireland because a hostile power controlling the island could block British naval access and threaten a maritime empire that controlled territories worldwide.
🇨🇳
China and Taiwan
Taiwan sits directly in the gap between Japan and the Philippines. If controlled by a hostile power, it blocks Chinese access to the Pacific Ocean and threatens Beijing's naval projection.
🇺🇸
United States and Cuba
Cuba controls the Straits of Florida through which half of US trade flows. A hostile foreign power using it as a base—as the Soviets did with nuclear missiles—poses an existential threat to American security and economic access.

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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.


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Strategic Options and Constraints

Washington prefers economic collapse and internal uprising over costly invasion.

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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.

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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.

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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.

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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.


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The Real Threat: Foreign Occupation, Not Cuba Itself

Cuba's weakness makes it vulnerable to exploitation by hostile great powers.

CUBAN MILITARY CAPABILITIES
No Offensive Threat to the United States
The Cuban army functions essentially as an internal police force and criminal enterprise. It can suppress the Cuban population but cannot project power against the United States. Cuba itself poses no direct military danger to American security or interests. The army's primary function is domestic control and cartel partnership, not external military operations.
FOREIGN POWER EXPLOITATION
Strategic Vulnerability to Outside Occupation
The danger lies in Cuba's potential as a base for hostile foreign powers—as happened with Spain in the 19th century and the Soviet Union during the Cold War. China could theoretically deploy troops or missiles to Cuba, transforming a manageable problem into an existential threat. This is why the Monroe Doctrine focused on Cuba and why the missile crisis nearly triggered nuclear war.

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Cuba's Catastrophic Reality

The economy has collapsed into third-world conditions with mass suffering.

Straits of Florida Width
90 miles
The narrow passage between Key West and Cuba through which roughly half of US imports and exports flow from the Gulf Coast.
Cuba's Length
Distance between New York and Chicago
Though thin, the island is long enough to effectively block Gulf access if controlled by a hostile power with modern naval capabilities.
Raúl Castro's Age
94 years old
The Cuban president now being indicted by the US Department of Justice for incidents from decades ago, part of symbolic pressure campaign.
Potential Cuban Refugees
Half a million
Estimated number of Cubans who might flee to Florida if economic and political conditions deteriorate further under US pressure.

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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.

George Friedman


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People

George Friedman
Chairman and Founder, Geopolitical Futures
guest
Christian Smith
Host
host
Donald Trump
President of the United States
mentioned
Raúl Castro
President of Cuba
mentioned
Marco Rubio
US Secretary of State
mentioned
Fidel Castro
Former Cuban Leader
mentioned
Theodore Roosevelt
Former US President
mentioned
Nicolás Maduro
Former President of Venezuela
mentioned

Glossary
Monroe DoctrineAn 1823 US policy declaring that European powers should not interfere in the Western Hemisphere, issued largely with Cuba in mind.
Straits of FloridaThe 90-mile-wide passage between Key West and Cuba through which roughly half of US Gulf Coast trade flows.
Bay of PigsA failed 1961 CIA-backed invasion of Cuba by Cuban exiles attempting to overthrow Fidel Castro.
Cuban Missile CrisisA 1962 confrontation between the US and Soviet Union over Soviet nuclear missiles deployed in Cuba that nearly triggered nuclear war.

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