Photo via Washington Examiner

Cut the oil, leak the secrets, feed the people: Trump’s blueprint to break Havana

Read the original at Washington Examiner ↗
Cite

Wargotz, E. (2026, September 23). Cut the oil, leak the secrets, feed the people: Trump’s blueprint to break Havana. Washington Examiner. https://www.washingtonexaminer.com/op-eds/4735707/us-gray-zone-strategy-cuban-regime-collapse/

Dated when The Aporia collected the article, usually within hours of publication. Check the original for its exact date and byline.

Washington Examiner · collected 2026-09-23 · by Eric Wargotz

Quick Summary

The Trump administration is employing a sophisticated strategy to destabilize the Cuban government by combining economic pressure with psychological warfare. This approach includes cutting off Cuba's supply of oil from Venezuela, causing widespread power outages and economic hardship, while simultaneously leaking classified information about covert operations aimed at undermining the regime's security apparatus internally. The article frames this tactic as a strategic alternative to traditional military intervention or embargoes, highlighting its effectiveness in destabilizing the Cuban government without direct military engagement.
Written by AI on 2026-09-23, from this article's own text only (the story summary below draws on all the coverage).

AI analysis

Story summary

The Trump administration is reportedly employing a sophisticated two-track strategy against Cuba, aiming to destabilize its 67-year-old communist regime without resorting to direct military action. This approach involves cutting off oil supplies crucial for Cuba's infrastructure while secretly leaking classified information to undermine the government's operational security and credibility. The U.S. is funneling aid through independent, faith-based organizations like Caritas Cuba and the Catholic Church, bypassing state authorities to distribute resources and prevent a humanitarian crisis. This strategy aims to avoid the complexities of direct military intervention while maximizing pressure on Havana, potentially preventing mass migration from the island just 90 miles off the coast of Florida.

Written for “Cuba Us Sanctions_policy” on 2026-10-31, grounded in this article and the 0 other(s) covering the same event.

Story

📰 Cuba Us Sanctions_policy
Politics · 1 article(s) covering the same event.

Compared with similar articles

This article reads leans strongly right and hedges 3% of its claims. Each row says how that neighbour differs.
The Straits Times
Hedges 5 of 27 claims Outlet record 66/100
“The articles describe different actions and strategies by President Trump involving distinct issues: one about national security related to a planned arch, and another about a sophisticated gray-zone campaign near Havana.”
Washington Examiner
⚖️ Leans strongly right Hedges 0 of 42 claims Outlet record 70/100
“The articles discuss different policy shifts under the Trump administration: one about evicting China from the Panama Canal and the other about a campaign against Havana, Cuba.”
CBS News
Hedges 1 of 3 claims Outlet record 66/100
“The articles describe different actions and timeframes related to U.S. strategy around Cuba.”
Al Jazeera
⚖️ Leans left further left than this Hedges 0 of 18 claims Outlet record 60/100
“The articles describe different aspects and stages of a broader conflict between the US and Cuba, not a single specific incident.”
The Straits Times
Hedges 0 of 9 claims Outlet record 66/100
“While both articles discuss Trump's stance on Cuba during his UN speech, they describe different aspects of the situation and are not clearly reporting on the same specific incident or occurrence.”
Euronews
⚖️ Centre further left than this Hedges 3 of 12 claims Outlet record 60/100
“The articles discuss related geopolitical actions against Cuba but describe different aspects of the situation (a deliberate leak vs. military preparation).”
How this article was measured signals, leaning charts, publisher record, byline, topics and claims

Signals How these are calculated →

Claims extracted
39
sentences that state something as happening or true
Uncertain
3%
1 of 39 hedged ("reportedly", "may", "according to")
Leaning
Leans strongly right
of the writing, not the subject · beta estimate
Publisher signals
70/100
Washington Examiner's corrections and hedging, across everything collected from it. Not a measure of accuracy.
Outlets on this story
1
Politics
Same framing elsewhere
1
articles that frame the event the way this one does
Analyzed 2026-09-23 · how these are computed

How this is being covered How these are calculated →

Article leaning vs. publisher reliability
Source leaning vs. consistency

Publisher

Washington Examiner · 3814 article(s) · 7 correction(s) detected
Running correction rate · 7 correction(s)

Who wrote this

Eric Wargotz
44 article(s) here · 1 carrying a prediction
🔮 The timing of this rapidly unfolding development could not be more dangerous.
🔮 But right now, all these conflicting voices in his ear, the domestic polling, and the foreign pressure might just be clouding his judgment.
🔮 A highly active, independent 85-year-old with multiple risk factors might experience significant, long-term survival benefits from continuous lipid management.
🔮 When we — whether ordinary citizens or high-level officials — flirt with systemic collapse simply because we despise the current administration, we play with a fire that will consume everyone.
🔮 National surveys published by the Pew Research Center Climate Pessimism Study document that roughly 60% of Americans express deep anxiety that global actors will fail to mitigate the worst environmental impacts due to political division.
2026-10-09 · assertive framing · The climate war’s dumbest lie: Jobs vs. nature
🔮 If your only window into the American soul is the nightly cable news broadcast, you would assume we are a nation completely irreconcilable, locked in a permanent cultural cold war.
🔮 Meanwhile, Trump boldly cut through the bureaucratic panic, signaling that the White House has no appetite for heavy-handed domestic regulations that would cripple our edge and stating that our primary guardrails remain the rule of law and the Department of Justice.
🔮 When we look at this disparity under the microscope, we find that it is neither a failure of individual willpower nor a consequence of an isolated genetic pool.
🔮 Every single time I hit “send” on a new draft, a cynical voice in my head asks the exact same questions: Will the editor accept this, as they’re overwhelmed with tons of these a day?
🔮 You cannot hide behind an ideological playbook or an army of insulated advisers when a budget needs balancing or a project stalls; your neighbors will call you out at the local hardware store.
Also by Eric Wargotz
Nothing else under this byline is closely related to this article, so these are simply their most recent.
All 44 articles by Eric Wargotz →

Topics

American Cuba Cuban Florida Washington

Subjects

Washington GPE · 5× Cuba GPE · 3× American NORP · 2× Cuban NORP · 2× the White House GPE · 2× Florida GPE · 1× Havana GPE · 1× Trump PERSON · 1× U.S. GPE · 1× the United States GPE · 1×

Narrative

By bypassing state authorities and funneling resources exclusively through independent, faith-based networks like Caritas Cuba and the Catholic Church to distribute the resources, the U.S. is providing a vital safety valve to prevent a chaotic mass-migration crisis.
framing: assertive · carried by 1 article(s) · first seen 2026-09-23
🔮 This realistic strategy achieves maximum leverage while completely avoiding the operational and humanitarian quagmires that a direct military conflict would inevitably trigger in our own backyard.
2026-09-23 · Washington Examiner
Cut the oil, leak the secrets, feed the people: Trump’s blueprint to break Havana · assertive framing

Claims (39 extracted, 1 hedged)

In the realm of modern geopolitics, a secret is rarely exposed by accident. asserted
secret → expose → accident
When granular details of classified American operations suddenly flood national headlines, it is almost always the result of a deliberate, calculated leak designed to serve as a weapon of psychological warfare. asserted
it → flood → warfare
This is the exact playbook the Trump administration is currently deploying just 90 miles off the coast of Florida. asserted
administration → deploy → Florida
While the legacy press remains utterly transfixed by the geopolitical aftershocks in Eastern Europe, Washington has quietly initiated a highly sophisticated gray-zone campaign aimed at forcing the total collapse of the 67-year-old Cuban communist regime. asserted
Washington → remain → regime
By masterfully orchestrating a two-track strategy of total infrastructure denial and deep-cover backchannel diplomacy, the administration is using weaponized media disclosures to shatter Havana’s operational security from the inside out. asserted
administration → orchestrate → inside
From an analytical standpoint, this is precisely the right strategy for the United States to pursue. asserted
States → pursue → standpoint
For decades, American foreign policy toward Cuba has been trapped in a rigid binary between passive embargoes and the politically fraught temptation of direct military intervention. asserted
policy → trap → intervention
The administration’s current approach wisely discards both options. asserted
approach → discard → options
By favoring asymmetric economic pressure and psychological subversion over the immense, unpredictable costs of a kinetic military invasion, Washington is executing a masterclass in modern power projection. asserted
Washington → favor → projection
This realistic strategy achieves maximum leverage while completely avoiding the operational and humanitarian quagmires that a direct military conflict would inevitably trigger in our own backyard. asserted
conflict → achieve → backyard
The baseline of this geopolitical squeeze is a brutal economic vise that has successfully paralyzed the island’s domestic infrastructure. asserted
that → paralyze → infrastructure
The pressure point was engineered under the dark of night when U.S. forces successfully removed former Venezuelan dictator Nicolas Maduro from power, a sudden maneuver that instantly severed Cuba’s primary lifeblood of subsidized crude oil. asserted
that → engineer → oil
To ensure the regime could not adapt, the White House immediately executed a de facto maritime blockade, leveraging aggressive tariff threats to freeze alternative petroleum shipments from secondary suppliers. uncertain
House → ensure → suppliers
Deprived of fuel, the island’s fragile electrical grid has recently suffered total, catastrophic failures, plunging the entire population into prolonged blackouts. asserted
grid → deprive → blackouts
The Cuban government now finds itself trapped in emergency triage, shuttering state offices and rationing power just to maintain a baseline of civil order. asserted
itself → find → order
Yet the true theater of consequence is unfolding far from public view, marked by an intentional pattern of administration leaks that have exposed Washington’s deep-cover operations. asserted
that → unfold → operations
In August, the CIA quietly established a highly specialized Cuba task force, surging cyber-analysts, case officers, and localized spy networks into the country. asserted
CIA → establish → country
This intelligence apparatus is actively probing the mid-level military officer corps, hunting for internal dissent to exploit as the civilian infrastructure crumbles. asserted
infrastructure → probe → dissent
By letting the existence of this covert cell slip to national newsrooms, Washington achieved a massive psychological victory without firing a single shot, forcing the regime’s leadership to realize that its internal communications are entirely compromised. asserted
communications → let → leadership
This calculated pressure is perfectly mirrored in the administration’s highly unorthodox backchannel diplomacy, which entirely sidesteps state structures. asserted
which → mirror → structures
The White House has initiated exclusive, secret talks with Raul Guillermo Rodriguez Castro, the 41-year-old grandson and close confidant of the 94-year-old revolutionary, Raul Castro. asserted
House → initiate → revolutionary
As a pragmatic business operator who currently manages the military-controlled enterprises driving 40% of the island’s economy, this young dynasty scion represents the ultimate point of leverage. asserted
scion → manage → leverage
Rather than angling for a bloody and unpredictable kinetic conflict, Washington’s envoys are utilizing these unpublicized channels to float a transition road map, offering protected economic concessions and personal immunity in exchange for real structural reform. asserted
envoys → angle → reform
When independent media outlets first broke the story of these backdoor meetings, senior administration officials notably refused to issue a denial. asserted
officials → break → denial
Instead, leadership publicly asserted that Washington will listen to anyone within the Cuban system who is open to making moves. asserted
who → assert → moves
This deliberate validation of the leak serves a brilliant strategic purpose: it sows deep, crippling paranoia within the upper echelons of the Communist Party. asserted
it → serve → Party
Mid-level officials are left wondering who has already flipped, effectively freezing the regime’s decision-making capabilities. asserted
who → leave → capabilities
Furthermore, these publicized maneuvers signal to global adversaries such as Russia and China that the administration views a regime alteration in Havana as an absolute inevitability. asserted
administration → publicize → inevitability
To completely disarm Havana’s anti-American propaganda machine during this collapse, the administration has paired its covert squeeze with an unprecedented humanitarian maneuver. asserted
administration → disarm → maneuver
In a historic logistical pivot, the State Department authorized a massive $100 million humanitarian aid package, utilizing weekly cargo flights from Miami to deliver vital food staples and medical gear directly to the population. asserted
Department → authorize → population
Crucially, the administration has completely boxed the communist regime out of the distribution chain. asserted
administration → box → chain
By bypassing state authorities and funneling resources exclusively through independent, faith-based networks like Caritas Cuba and the Catholic Church to distribute the resources, the U.S. is providing a vital safety valve to prevent a chaotic mass-migration crisis. asserted
U.S. → bypass → crisis
Ultimately, this two-track strategy represents a fundamental departure from the failed, rigid isolation policies of the past 50 years. asserted
strategy → represent → years
On the surface, the fuel blockade is grinding the regime’s infrastructure to absolute dust, while behind closed doors, a quiet intelligence surge and backchannel statecraft are actively preparing the terrain for a managed transition of power. asserted
surge → grind → power
By trading the temptation of a direct military invasion for a sophisticated campaign of infrastructure denial and unyielding humanitarian subversion, Washington is successfully rewriting the rules of engagement in our hemisphere. asserted
Washington → trade → hemisphere
This realistic, gray-zone methodology is precisely how a superpower should flex its muscles. asserted
superpower → flex → muscles
The high-stakes dance with Havana is well underway, and by avoiding military overreach, the administration is forcing the communist regime to stumble to a halt entirely on its own terms. asserted
administration → avoid → terms
Eric Wargotz, M.D., is a geopolitical analyst and policy commentator who has held leadership roles across government and medicine. asserted
who → hold → government
, he is a former U.S. Senate nominee and elected county commission president. asserted
he → elect → ?
💬Give feedback
🕘History 🎫Support