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Thursday, July 23, 2026

THE NEW RED SCARE: TRUMP SETS SIGHTS ON CUBA


THE NEW RED SCARE: TRUMP SETS SIGHTS ON CUBA

Or: How I Learned to Stop Worrying and Love the Embargo

"Nobody told me there'd be days like these / Strange days indeed / Most peculiar, mama…" — John Lennon

Strange days, indeed. While America cheerfully imports $500 billion worth of goods annually from Communist China — the actual, card-carrying, Mao-portrait-hanging, five-year-plan-writing Communist Party of China — the Trump administration has decided that the real existential threat to Western civilization is a Caribbean island of 11 million people whose most fearsome export is good cigars and world-class orthopedic surgeons. Welcome, America, to the New Red Scare — same as the old Red Scare, but with better social media and worse geopolitical logic.

The Ghost of McCarthy Wears a MAGA Hat

Here's the delicious irony at the heart of Trump's Cuba obsession: the United States currently trades enthusiastically with three communist nations — China, Vietnam, and Laos. We buy Chinese iPhones. We vacation in Vietnamese beach resorts. We source Laotian coffee for our artisanal Brooklyn cafĆ©s. Nobody in the Cabinet is losing sleep over the ideological purity of their supply chain.

But Cuba? Ninety miles of warm Caribbean water away? That's where freedom goes to die.

Secretary of State Marco Rubio — a man who approaches Cuba policy with the barely-contained enthusiasm of a golden retriever spotting a tennis ball — released a 99-page State Department dossier grandly titled "Cuba: The Capital of 21st Century Communism." Ninety-nine pages. To put that in perspective, the U.S. intelligence community's assessment of China's military buildup runs shorter. Apparently, a crumbling island nation experiencing rolling blackouts and a mass emigration crisis poses a more urgent documentation challenge than a nuclear-armed superpower with a $19 trillion economy.

The document accused Havana of cultivating left-wing groups on American soil and building a "revolutionary infrastructure" in the United States. Critics — including most historians who've read a book published after 1965 — called it McCarthyism with a glossy cover page. Senator McCarthy, at least, had the decency to do his red-baiting in person. The modern version outsources it to a 99-page PDF.

The Maximum Pressure Maximally Confused Policy

The Trump administration's Cuba strategy — branded with the militaristic panache of a Tom Clancy novel as "Maximum Pressure 2.0" — involves a naval oil blockade, expanded sanctions, asset freezes, and the occasional presidential musing about a "friendly takeover" of Havana.

A friendly takeover. Of a sovereign nation. That didn't ask.

Executive Order 14380 threatens secondary tariffs on any foreign energy company — including Mexico's state oil giant Pemex — that dares supply petroleum to Cuba. The result has been predictable: nationwide blackouts, food production collapse, and medicine shortages for ordinary Cubans who, it bears repeating, did not personally design the Cuban Missile Crisis.

The policy logic, such as it is, runs roughly as follows:

Cuba is communist → Communism is bad → Therefore, making Cuban grandmothers unable to refrigerate insulin is a blow for freedom.

Meanwhile, Apple's latest quarterly earnings report shows record profits from its Chinese manufacturing partnerships. The Communist Party of China sends its regards.

Rubio's Revenge Fantasy and the Florida Factor

To understand the emotional engine driving this policy, one must understand Marco Rubio — Secretary of State, Florida senator emeritus, and a man for whom Cuba policy is less a diplomatic portfolio than a deeply personal psychodrama.

Rubio's political identity was forged in the crucible of Miami's Cuban exile community, where the 1959 revolution is not ancient history but a living wound. His hawkish Cuba stance isn't merely calculated electoral positioning — though it certainly is that, given Florida's powerful Cuban-American voting bloc — it appears to be genuine, visceral, and occasionally alarming in its intensity.

When Trump floats the idea of military intervention in Cuba, Rubio does not appear to be the voice of restraint in the room. This is a man who, confronted with the prospect of regime change in Havana, reportedly has the energy of someone who just found out the restaurant still has the special.

The Cuban-American political machine — built over six decades by organizations like the Cuban American National Foundation, modeled deliberately on AIPAC's lobbying playbook — has been extraordinarily effective. It helped pass the Helms-Burton Act in 1996, which codified the embargo into statutory law so thoroughly that no president can lift it without an act of Congress. It has elevated Cuban Americans to the Senate, the House, and now the Cabinet. It has, in effect, allowed the politics of a 90-mile island to reshape the politics of the world's largest superpower.

Not bad for a country whose GDP is smaller than the city of Tampa's.

The Geopolitical Whiplash World Tour

Trump's foreign policy, viewed from sufficient altitude, resembles nothing so much as a man navigating a maze by walking directly into every wall. Consider the ideological consistency on display:

CountryPolitical SystemTrump Policy
ChinaCommunist (1.4 billion people)Trade war, then trade deal, then golf diplomacy
VietnamCommunist (97 million people)Preferred manufacturing partner
CubaCommunist (11 million people)Naval blockade, regime change rhetoric
Saudi ArabiaAbsolute monarchySword dances and arms deals
North KoreaNuclear-armed dictatorship"Beautiful letters," "great chemistry"
NATO AlliesLiberal democracies"Pay up or we leave"

The pattern, if one squints philosophically, is not actually anti-communism. It is something more primal: Trump likes strongmen who flatter him and dislikes governments that don't. Cuba's sin is not Marxism-Leninism. Cuba's sin is that Havana has never sent a delegation to Mar-a-Lago bearing gifts and compliments.

Kim Jong-un sent a letter. He got a summit. Xi Jinping invited Trump to the Forbidden City. He got a trade deal. Cuba sent nothing. Cuba gets a blockade.

The foreign policy doctrine, stripped of its ideological dressing, appears to be: "Be nice to Donald, or suffer." It's less Kissinger, more kindergarten.

Hiding Iran's Failure Behind the Malecon

There is, of course, a more cynical reading of the Cuba escalation — and in Washington, the cynical reading is usually the correct one.

The Iran negotiations, launched with considerable fanfare and presidential self-congratulation, have produced results ranging from inconclusive to embarrassing. The nuclear program continues. The regional proxy network persists. The Revolutionary Guard remains unimpressed. When a foreign policy initiative fails to deliver the promised triumph, the time-honored Washington solution is to find a different foreign policy initiative to talk about instead — preferably one that involves a smaller, weaker adversary who cannot meaningfully retaliate.

Cuba, conveniently, cannot shoot back. Cuba cannot impose counter-sanctions that damage the American economy. Cuba cannot threaten American cities with ballistic missiles — or rather, it could in 1962, but that required Soviet hardware and ended rather badly for everyone involved. Cuba is, in the language of geopolitical bullying, a safe target: loud enough to generate headlines, weak enough to absorb the pressure without consequence.

It is the foreign policy equivalent of picking a fight with someone half your size because the person your own size just embarrassed you.

The Ghost of Bay of Pigs Past

Before the current administration gets too excited about Caribbean regime change, it might be worth reviewing the historical record — which is, to put it diplomatically, not encouraging.

The Bay of Pigs invasion (1961): 1,400 CIA-trained Cuban exiles. Three days. Complete catastrophe. Castro's forces captured nearly 1,200 men. JFK was humiliated on the world stage. The operation so thoroughly backfired that it arguably accelerated Soviet nuclear deployment to Cuba, producing the Cuban Missile Crisis — the closest humanity has come to thermonuclear annihilation since the invention of thermonuclear weapons.

The CIA then spent the better part of a decade trying to assassinate Fidel Castro. The Church Committee documented at least eight distinct plots, including: poison pills slipped into milkshakes, a diving suit dusted with lethal fungus, an exploding seashell planted at his favorite dive site, and — this is real — a ballpoint pen rigged with a hypodermic needle filled with deadly poison, delivered to a Cuban official on the same day JFK was assassinated in Dallas. The universe, apparently, has a sense of irony.

Castro died in 2016. Of old age. At 90.

The lesson of six decades of American covert action against Cuba is straightforward: the Cuban government is significantly better at this than we are. The DGI — Cuba's intelligence service — ran double agents so effectively that when a senior Cuban intelligence officer defected to the CIA in 1987, he revealed that virtually every Cuban asset the CIA had recruited since 1961 was actually a double agent. Decades of intelligence reports fed to Washington had been carefully crafted Cuban disinformation. The CIA had been, in essence, paying for its own manipulation.

The Ana Montes case — a senior Defense Intelligence Agency analyst who spied for Cuba for 17 years, memorizing classified documents and transmitting them home via shortwave radio — suggests that Cuban intelligence's penetration of American institutions did not exactly end with the Cold War.

Perhaps, before launching Maximum Pressure 2.0, someone in the administration might read the manual from Maximum Pressure 1.0 through 1.9 and note the consistent outcome.

Insanity as Foreign Policy: A Brief Taxonomy

The Trump administration's approach to the world can be summarized in a simple framework:

  • Dictators who compliment Trump: Beloved. Invited to dinner. Described as "very smart" and "strong leaders."
  • Democratic allies who question Trump: Freeloaders. Threats. Subjected to tariffs and public humiliation.
  • Small communist nations: Existential threats requiring naval blockades.
  • Large communist nations with nuclear weapons and $500 billion in trade: Complicated. Let's do golf.

The philosopher Immanuel Kant proposed that a rational foreign policy should be guided by universal principles consistently applied. The Trump Doctrine proposes something different: foreign policy as mood ring, reflecting whatever combination of personal grievance, electoral calculation, and cable news cycle happens to be dominant on a given Tuesday morning.

Strange days, indeed. Most peculiar, mama.

EPILOGUE: A Bedtime Story for Warmongers

With sincere apologies to the estate of Theodor Seuss Geisel — and to the Cuban people, who deserve better from their 90-mile neighbor.



I Do Not Like That Island Cuba!

A Tale by Donald-I-Am

I am Donald. Donald-I-Am. That Donald-I-Am! That Donald-I-Am! I do not like That Donald-I-Am!

Do you like That island Cuba?

I do not like it, Donald-I-Am. I do not like That island Cuba!

Would you like it With some trade? Would you like it If a deal was made?

I would not like it With some trade. I would not like a deal that's made. I do not like that island Cuba! I do not like it, Donald-I-Am.

Would you like it With a boat? Would you like it If their oil's afloat?

Not with a boat! Not if it floats! Not with their oil! Not on their soil!

I do not like it with some trade. I do not like a deal that's made. I do not like that island Cuba! I do not like it, Donald-I-Am.

Would you like them In the West? Do you think Their cigars are best?

Not in the West! Not with their best! Not with a boat! Not if it floats!

I do not like them near or far, I do not like a single cigar! I do not like that island Cuba! I do not like it, Donald-I-Am.

Could you, would you, With Marco R.? Could you, would you, In a golf cart car?

I would not, could not, With Marco R.! I would not, could not, In my golf cart car!

Not in the West! Not with their best! Not with a boat! No fuel afloat!

I do not like them here or there. I do not like them ANYWHERE!

I do not like That island Cuba! I do not like it, Donald-I-Am!

The End.

— Though history suggests it never really is.

"Strange days indeed / Most peculiar, mama." — John Lennon, who also understood that the most dangerous men are the ones who confuse belligerence with strength, and noise with policy.

The author notes that the United States and Cuba are 90 miles apart, have been neighbors for centuries, and that ordinary Cubans — who did not personally design the 1962 missile deployment — are the ones living without electricity, medicine, and food as a result of policies crafted by comfortable men in air-conditioned offices in Washington and Miami. History will have opinions about this. History usually does.


SOURCES & REFERENCES

The New Red Scare: Trump Sets Sights on Cuba

šŸ”“ The New Red Scare & Rubio's Cuba Dossier

šŸ›¢️ Executive Order 14380 & The Naval Oil Blockade

šŸ· The Bay of Pigs Invasion (1961)

šŸŽ­ Operation Northwoods (1962)

šŸ“– Additional Recommended Reading

(From the article's historical background — well-established sources)

šŸ’” Note: All links were verified as active as of July 23, 2026. The White House EO link, State Department report, and Baker McKenzie sanctions analysis are primary or legal sources and carry the highest evidentiary weight for the policy claims made in the article.



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