Executive Summary
The strategic landscape of the Caribbean has undergone a foundational and potentially irreversible shift during the final week of January 2026. This period marks the convergence of a total collapse in Cuba’s external energy security with the most aggressive posture from the United States in the post-Cold War era.1 Following the successful kinetic intervention in Venezuela on January 3rd, 2026, known as “Operation Absolute Resolve”, the Trump administration has pivotally transitioned its “maximum pressure” campaign toward the Cuban archipelago, framing the Havana regime as the ideological and security architect of the deposed Maduro government.1 This policy shift is codified in the “Trump Corollary” to the Monroe Doctrine—the so-called “Donroe Doctrine”—which asserts a proactive right of the United States to eliminate the influence of extra-regional adversaries such as Russia, China, and Iran from the Western Hemisphere.2
The defining event of the current reporting period is the January 29th Executive Order, “Addressing Threats to the United States by the Government of Cuba,” which declared a National Emergency and established a novel tariff-based secondary sanctions mechanism.6 This mechanism effectively mandates a global blockade of oil supplies to Cuba by threatening ad valorem tariffs on any nation providing petroleum products to the island, either directly or indirectly.6 This has placed immediate and severe pressure on the government of Mexico, which remains one of Cuba’s final energy lifelines.2
Internally, the Cuban state is navigating a poly-crisis of unprecedented proportions. The loss of the Venezuelan oil subsidy—amounting to approximately 30,000 to 35,000 barrels per day—has resulted in a catastrophic failure of the national electrical grid, with blackouts now persisting for 12 to 20 hours daily.1 The Cuban Communist Party (PCC) has responded with ideological entrenchment, utilizing the 173rd anniversary of José Martí’s birth and the centennial of Fidel Castro’s birth to mobilize the “War of the Entire People” doctrine.14 The National Defense Council has formally met to analyze “State of War” transition measures, signaling that the regime views the current U.S. posture as an imminent existential threat.16
Demographically, the island is facing an existential hollow-out. Population estimates suggest the total number of inhabitants has fallen below 8 million, a 25% decline in just four years, driven by the mass exodus of the productive-age population.19 As the U.S. Coast Guard intensifies maritime interdictions in the Florida Straits, the likelihood of a managed migration crisis—historically used by Havana as a “safety valve”—is increasing, even as the Trump administration signals it will no longer tolerate such asymmetric statecraft.20
Strategic Threat Assessment: The Donroe Doctrine and Hemispheric Hegemony
The overarching strategic framework governing the current crisis is the re-assertion of U.S. hemispheric hegemony through the “Trump Corollary” to the Monroe Doctrine.3 This doctrine, reinforced by the release of the 2025 National Security Strategy, represents a shift from containment to active rollback of authoritarian regimes in the Western Hemisphere.3 National security analysts note that the administration views the capture of Nicolás Maduro not as an end in itself, but as the necessary precondition for the dismantling of the “Bolshevik-Castroite” axis that has defined regional anti-Americanism for two decades.1
The primary architect of this hardened policy, Secretary of State Marco Rubio, has explicitly linked the survival of the Cuban regime to its provision of “Security Services” for regional dictators.2 The administration’s rhetoric emphasizes that the era of strategic immunity for Havana—where the U.S. relied on diplomatic isolation and limited sanctions—has ended.3 The operational success of the raid in Caracas has served as a “strategic shock,” demonstrating that the United States possesses the political appetite and the kinetic capability to target heads of state directly within their fortified compounds.3
This shift has profoundly altered elite risk calculations within Havana. Intelligence indicators suggest that the Cuban Revolutionary Armed Forces (FAR) and the Ministry of the Interior (MININT) are currently engaged in a massive reassessment of their own internal security protocols.3 The destruction of the Cuban praetorian guard in Venezuela, which resulted in 32 combat deaths, has shattered the myth of the Avispas Negras (Black Wasps) as an insurmountable deterrent against U.S. special operations.1
| Strategic Indicator | Pre-2026 Baseline | Current Status (Jan 31, 2026) | Strategic Implication |
| U.S. Intervention Threshold | Diplomatic/Economic Sanctions | Kinetic/Regime Change Operations | High Risk of Direct Intervention 3 |
| Regional Alliance Structure | Strong Havana-Caracas Axis | Axis Severed; Maduro Captured | Cuba Isolated Energy-wise 2 |
| Energy Subsidy Volume | 35,000 bpd (Venezuela) | Zero bpd from Venezuela | Total Grid Instability 2 |
| Diplomatic Engagement | Limited/Intermittent | Zero/Hostile (National Emergency) | Path to Conflict Escalation 6 |
The Geopolitical Shock of Operation Absolute Resolve
The psychological impact of the January 3rd raid on Caracas continues to reverberate through the Cuban military establishment. The precision of the Delta Force operation, which facilitated the capture of Maduro while neutralizing his Cuban security detail, has created a sense of vulnerability within the Cuban leadership that has not been seen since the 1962 Missile Crisis.1
Foreign affairs analysts identify the repatriation of the 32 Cuban military remains on January 15th as a watershed moment in the domestic narrative.1 The public ceremony at José Martí International Airport, attended by President Miguel Díaz-Canel and General Raúl Castro, was intended to project “deep pride” and national resolve, but intelligence assessments suggest it has also fueled anxiety among the rank-and-file of the FAR.1 These were the first direct combat deaths of Cuban personnel at the hands of the U.S. military since the invasion of Grenada in 1983.1
The tactical failure of the Cuban-advised defense systems in Caracas—where air defenses were caught out in the open and surveillance networks were bypassed—has forced the Cuban National Defense Council to reconsider the “War of the Entire People” strategy.4 This strategy relies on the mass mobilization of the civilian population to make any occupation of the island prohibitively expensive.16 However, the speed and technological superiority demonstrated by U.S. follow-on forces in Caracas suggests that a “surgical” regime-change operation might be attempted in Havana without a large-scale conventional invasion.3
The January 29 Executive Order: Anatomy of the Tariff Weapon
The signing of the Executive Order “Addressing Threats to the United States by the Government of Cuba” on January 29th, 2026, represents the most significant escalation of economic warfare against the island in decades.6 This order utilizes the International Emergency Economic Powers Act (IEEPA) to declare the actions of the Cuban government an “unusual and extraordinary threat” to U.S. national security.6
The mechanism of this order is structurally unique. Rather than relying solely on traditional “blocking” sanctions, it establishes an “ad valorem tariff” system targeted at third-party countries that provide oil to Cuba.6 This is designed to force a zero-sum choice for nations like Mexico, Russia, and Algeria: continue supplying the Cuban energy market or face punitive duties on their entire export volume to the United States.6
Section 2 of the Executive Order provides the Secretary of Commerce with the authority to determine if a country is providing oil to Cuba, either “directly or indirectly”.6 The inclusion of the word “indirectly” is a critical legal lever, as it covers the resale of petroleum products through intermediaries or third-party refineries where the original seller has “knowledge that such oil may be provided to Cuba”.6 This creates a massive legal liability for international energy trading firms and national oil companies (NOCs).7
Multi-Agency Enforcement Framework
The enforcement architecture for this National Emergency is highly decentralized, involving several key cabinet-level departments:
- Department of Commerce: Responsible for the initial finding that a foreign country is providing oil to Cuba.6
- Department of State: Responsible for recommending the specific tariff rates to the President after consulting with the Treasury and the U.S. Trade Representative.6
- Department of the Treasury: Provides technical guidance on financial transactions and “indirect” ownership structures.6
- Department of Homeland Security (DHS): Charged with monitoring the potential for “asymmetric retaliation” via migration or cyber activity.6
This framework effectively establishes a “maritime oil quarantine” without the need for a kinetic naval blockade, as the economic cost of non-compliance is so high that most commercial carriers will likely self-select out of the Cuban market.2
Macroeconomic Collapse: The Energy Cliff and Monetary Instability
The cessation of Venezuelan oil shipments has pushed the Cuban economy into a state of “uncontrolled descent”.3 For nearly two decades, the Cuba-Venezuela axis provided Havana with roughly 50% of its oil needs in exchange for human services (medical and security personnel).1 This barter arrangement allowed the regime to generate hard currency by reselling surplus oil to China, a practice that has now been completely terminated.1
The current energy deficit is estimated at 30,000 to 35,000 barrels of oil per day.1 This shortfall has catastrophic ripple effects across the entire economic matrix:
| Sector | Impact of Oil Cutoff | Observable Metric |
| Power Grid | Chronic fuel shortages for thermal plants | 20-hour daily blackouts 12 |
| Transportation | Total cessation of public bus services | Multi-mile fuel queues 12 |
| Agriculture | Lack of fuel for transport/pumping | 60% increase in food prices 13 |
| Healthcare | Failure of vaccine/medication refrigeration | Increased reliance on foreign donations 2 |
| Water | Failure of treatment and pumping stations | Water-borne illness risk 2 |
National security analysts emphasize that this is not a temporary shortage but a structural cliff. Even if Cuba attempted to buy oil on the world market, it lacks the necessary hard currency and creditworthiness to do so.1 The island’s economy contracted by 15% between 2018 and 2024, with an additional 4% decline in 2025 alone.20
Currency Devaluation and Stagflation
The monetary landscape is equally unstable. On January 5th, the Central Bank of Cuba (BCC) announced a managed floating exchange rate system to combat the soaring black-market value of the US Dollar.28 The launch of a third “floating” rate at 410 CUP to 1 USD was intended to bring liquidity back into the formal banking system, but as of late January, the rate has already depreciated further, with Cadeca rates reaching 466 CUP to 1 USD.28
Independent economists such as Pavel Vidal and Pedro Monreal describe the current situation as the worst year of “stagflation” (stagnant growth combined with hyperinflation) since the 1959 Revolution.30 While the government claims an official inflation rate of 14.07% for 2025, analysts suggest the “real-world” figure, which includes informal market prices where most citizens acquire food, is closer to 70%.30 This massive erosion of purchasing power is a primary driver of social discontent and the “universal aspiration” for emigration.19
Internal Security and Military Posture: The State of War Transition
In response to the U.S. National Emergency declaration and the kinetic precedent in Venezuela, the Cuban Communist Party has shifted the country to a defensive footing.16 This involves both ideological mobilization and tactical military exercises.
Ideological Entrenchment
The regime has leveraged the 173rd anniversary of José Martí’s birth (January 28th) to rally the population.14 The “March of the Torches,” a tradition dating back to 1953, saw tens of thousands of participants, primarily university students and youth organizations, marching through Havana in a show of defiance.14 During these events, speakers—including President Díaz-Canel—framed the U.S. “maximum pressure” campaign as “genocidal” and “fascist”.12
The state media apparatus has also launched a campaign to commemorate the centennial of Fidel Castro’s birth (1926-2026), using his historical resistance against the United States as the template for current policy.14 This narrative is designed to suppress internal dissent by labeling any domestic opposition as “mercenaries” or “annexationists” working for Washington.6
The National Defense Council and “State of War” Plans
Intelligence reports confirm that the National Defense Council met during the final week of January to “analyze and approve plans and measures for transitioning to a State of War”.16 While the 2019 Constitution allows for several extraordinary states—including General Mobilization and State of Emergency—the formal discussion of a “State of War” indicates that the regime believes kinetic military aggression is a distinct possibility.16
Tactical military exercises were supervised by Díaz-Canel and General Alvaro Lopez Miera, the Minister of the Armed Forces.16 These drills included tank maneuvers and air defense coordination, though analysts note that much of the equipment remains technologically inferior to U.S. capabilities.3 The regime’s strategy remains “War of the Entire People,” which focuses on:
- Asymmetric Deterrence: Making the “cost of aggression” too high for the U.S. through civilian mobilization.16
- Hardening of Targets: Attempting to protect command-and-control centers from surgical drone or SOF strikes.4
- Internal Control: Using the Revolutionary Defense Committees (CDR) to monitor neighborhoods for signs of a U.S.-backed uprising.35
Foreign Relations: The Fragile Authoritarian Nexus
Cuba’s foreign policy during this crisis period is focused on securing emergency lifelines from extra-regional powers, specifically China and Russia.38
The Chinese Strategic Partnership
Beijing has reiterated its “firm support” for Cuba in the face of U.S. threats, condemning the blockade and the “State Sponsor of Terrorism” designation.38 This support is both rhetorical and material. On January 20th, the first part of a 60,000-ton shipment of rice arrived in Havana, providing critical food aid at a moment of acute shortage.39
However, intelligence analysts note that China’s engagement is carefully calibrated to avoid a direct military confrontation with the United States over the island.3 While China has expanded its signal intelligence (SIGINT) facilities in Cuba to monitor U.S. communications, it has not shown a willingness to underwrite the Cuban economy with the same level of subsidy that Venezuela once provided.3 Beijing’s primary interest appears to be the maintenance of a strategic surveillance platform on the U.S. doorstep rather than the long-term survival of the Communist Party of Cuba.3
The Russian Security Guarantee
Moscow has also maintained a high-level presence in Havana. On January 21st, Russian Interior Minister Vladimir Kolokoltsev led a delegation of officials and military personnel to meet with Díaz-Canel.39 This visit followed a statement by Vladimir Putin affirming that Russia will “continue to provide assistance” to defend Cuba’s sovereignty “by all means”.39
The State Duma ratified new agreements on military cooperation with Cuba in late 2025, providing a legal framework for joint training and potentially the basing of Russian assets on the island.43 For Moscow, Cuba remains a critical piece of “strategic depth”—a counter-weight to NATO’s presence in Eastern Europe.43 Nevertheless, like China, Russia’s ability to provide massive energy subsidies is limited by its own ongoing involvement in the Ukraine conflict and the logistical challenges of transporting large volumes of oil across the Atlantic under a U.S. tariff threat.38
Sociological Indicators: The Migration Crisis and State Legitimacy
The most profound threat to the Cuban state is not external invasion, but internal demographic and social collapse. The “poly-crisis” of energy, food, and medicine has eroded the “social contract” established in 1959.19
Demographic Hollow-Out
The population of Cuba is shrinking at an alarming rate. Demographics experts report that the population has dropped by 1.4 million since 2020, with recent estimates placing the total population below 8 million.19 This represents a 25% decline in the total population in just four years.19
| Demographic Metric | Value/Trend (Jan 2026) | Societal Impact |
| Total Population | < 8 Million | World’s fastest population decline 19 |
| Age of Emigrants | 15–59 (77% reproductive age) | Accelerator of economic/social decline 19 |
| Fertility Rate | Below replacement since 1978 | Long-term labor shortage 19 |
| Elderly Population | 1 in 4 Cubans over age 60 | Severe strain on health/pension systems 19 |
For young Cubans, emigration is no longer a choice but an “almost universal aspiration”.19 Those who remain face a daily struggle for survival. Public services, including waste collection, have largely collapsed, with “piles of garbage” accumulating in Havana’s streets, fueling both public health concerns and localized protests.19
Migration as Asymmetric Statecraft
Historically, the Cuban government has used “migration crises” as a weapon of statecraft. By facilitating the departure of thousands of citizens—as seen during the Mariel Boatlift (1980) or the Rafter Crisis (1994)—Havana creates a domestic political crisis in the United States, forcing the White House to the negotiating table.19
Intelligence analysts suggest that Díaz-Canel may be preparing for a similar move in early 2026. However, the current U.S. administration has signaled it will view a managed migration surge as a “hostile act” under the new National Emergency.6 The U.S. Coast Guard (USCG) Seventh District has intensified its presence in the Florida Straits, conducting frequent interdictions and repatriating migrants “without incident” as a deterrent.22
Intelligence Assessment: Foreign Surveillance and Counter-Intelligence
A critical component of the national security threat posed by Cuba is its role as a regional intelligence hub for U.S. adversaries.6 The January 29th Executive Order explicitly cites Cuba’s cooperation with “hostile countries” and “transnational terrorist groups”.6
SIGINT and Surveillance Infrastructure
The U.S. government has expressed “deep concern” regarding Chinese-funded signals intelligence facilities across the island.6 These sites are reportedly capable of monitoring:
- U.S. Military Operations: Specifically those originating from Southern Command and Florida-based bases.6
- Commercial Shipping: Monitoring of the vital sea lanes of the Caribbean and the Florida Straits.6
- Space Launches: Intercepting telemetry and communication data from Cape Canaveral.42
- Sensitive Communications: Stealing national security information via Russian SIGINT facilities.6
The presence of these assets suggests that Cuba is being used as a “forward operating base” for electronic warfare and espionage.42 The administration has indicated that the removal of these facilities is a non-negotiable condition for any future “deal” with Havana.2
Ties to Transnational Terrorist Groups
The Executive Order also designates Cuba as a “safe environment” for groups such as Hamas and Hezbollah.6 While independent analysts debate the extent of this cooperation, the U.S. intelligence community asserts that the Cuban regime provides logistical support and a diplomatic platform for these groups to “build economic, cultural, and security ties” throughout Latin America.6 This “destabilization” effort is seen as a direct threat to the safety of the American people and the stability of the Western Hemisphere.6
Strategic Conclusions and Risk Forecast
The confluence of events in January 2026 has brought Cuba to a critical strategic inflection point.3 The “Venezuela Precedent” has overturned the assumption of U.S. restraint, while the “Tariff Weapon” has created a terminal threat to the island’s energy security.3
Short-Term Risk Forecast (February 2026)
- Total Grid Collapse: There is a high probability of a “Black Start” failure of the national electrical grid if Mexico halts oil shipments in response to U.S. tariffs.11 A total blackout lasting more than 48 hours could trigger localized unrest that the security forces may struggle to contain without lethal force.26
- Elite Fragmentation: If the U.S. continues to target the military-run conglomerate GAESA and the Castro family nucleus with personalized sanctions, we may see a “splintering” of the Cuban elite.3 Security and military actors may seek a “negotiated transition” to preserve their own economic interests, despite the official “State of War” rhetoric.3
- Migration Flotilla: As the economic situation hits “subsistence mode,” the likelihood of a mass migration attempt—either spontaneous or state-facilitated—is high.19 This would test the limits of the USCG’s interdiction mission and the administration’s “zero tolerance” policy.6
- Diplomatic Escalation: Expect Havana to seek an emergency session of the UN General Assembly to condemn the “energy blockade”.15 Russia and China will likely use this forum to challenge the “Donroe Doctrine” as a violation of international law.38
In conclusion, the Cuban regime is more vulnerable today than at any time since 1959.1 The loss of the Venezuelan lifeline is a “strategic shock” from which the current economic model cannot recover.3 The Trump administration appears committed to a policy of regime change by economic asphyxiation, banking on the theory that sustained pressure will either force the leadership to “make a deal” or trigger a popular uprising.1 The enduring ideological resilience of the PCC and the support of extra-regional adversaries remain the primary hurdles to this objective.2
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