Simmering / Americas
Venezuela Political Crisis
Twin earthquakes expose Venezuela's hollowed state capacity as Washington deepens its protectorate grip over the transition.
The United States and Cuba have been locked in a standoff since 1959, when Fidel Castro's revolution overthrew the Batista government and nationalized American assets.
Washington answered with a trade embargo in 1962, and the two countries have been stuck there ever since. A brief Obama-era thaw was reversed under Trump, who redesignated Cuba a state sponsor of terrorism in 2021. Russia and Venezuela keep the island's economy on life support, with Chinese solar parks now plugging gaps in a collapsing grid. The US coordinates human rights pressure with the EU.
The embargo has outlasted ten US presidents and the Soviet Union itself, and neither side has a theory for how it ends.
Cuba crossed a threshold held for 67 years in June 2026, rushing through 176 emergency economic reforms including private banking and foreign sale of state assets, a move that signals the depth of regime distress rather than a credible recovery path.
It matters because the frozen conflict continues to tie down the main belligerents, pull in outside backers, and shape the security balance across Americas.
Weekly net escalation pressure, last 90 days
Cuba's 176-measure economic overhaul is the clearest indicator yet of regime distress: permitting private banks and foreign sale of state assets crosses a threshold the Castro government held for 67 years.
The death of Ramiro Valdes Menendez removes the last foundational pillar of the revolutionary coercive apparatus at the moment of maximum external pressure.
Washington's pressure campaign has no articulated endgame: Trump's 'taking Cuba' rhetoric, Hegseth's Guantanamo visit, criminal indictments of Raúl Castro.
Amid economic collapse, blackouts, and scarcity, Cuba records its highest emigration levels in history, with over 300,000 Cubans fleeing to the United States in a single year.
On July 11, tens of thousands of Cubans take to the streets in the largest anti-government protests since 1959; the government responds with mass arrests of hundreds of demonstrators and activists.
The Trump administration reverses much of the Obama-era opening, reinstating and expanding sanctions and redesignating Cuba as a state sponsor of terrorism in 2021.
Presidents Obama and Raúl Castro announce a historic diplomatic thaw, restoring embassies and easing some travel and trade restrictions — the most significant shift in relations in over 50 years.
The collapse of the Soviet Union ends Cuba's main economic lifeline, triggering the "Special Period" of severe shortages and spurring the first major post-revolution internal protests in 1994.
The US imposes a full trade embargo following Cuba's nationalization of American assets; the embargo becomes the central mechanism of US pressure and a defining grievance of the Cuban government for decades.
The US-backed Bay of Pigs invasion fails catastrophically, hardening the Castro government's posture toward domestic dissent and cementing the exile diaspora as a permanent opposition force.
Fidel Castro's revolution overthrows the Batista government, establishing a one-party socialist state and triggering the first wave of Cuban exiles fleeing to the United States.
Venezuelan petroleum supply chain: Cuba's primary subsidized fuel lifeline, effectively severed since January 2025 under U.S. blockade pressure.
Russian sanctioned tanker fleet: attempted alternative petroleum deliveries to Cuba as a secondary supply vector after the Venezuelan cutoff.
Vanguard Energy: attempted a 250,000-barrel fuel transaction with Cuba via direct access to government storage facilities.
Cupet (Cuban national oil company): sanctioned by U.S.
Treasury to close the legal perimeter around unauthorized energy transactions.
PRC state-linked SIGINT infrastructure: the completed Bejucal circularly disposed antenna array, linked to Chinese support by CSIS.
Cuba sustained economically by Venezuela and Russia; US coordinates with EU on human rights pressure
Jun 27, 2026
De-escalating
Diplomatic
Trump Administration Targets Cuba After Venezuela and Iran Interventions
Following the U.S.-backed ouster of Venezuela's Nicolás Maduro in January and the elimination of Iran's senior leadership in February, the Trump administration has turned pressure toward Cuba through an oil blockade now in its fifth month.
Jun 26, 2026
Escalating
Diplomatic
U.S. Disaster Response Deepens Influence Over Post-Maduro Venezuela
Washington organized a 250-person disaster-assistance response to Venezuela's earthquakes, layered atop a broader consolidation of influence since U.S. forces removed Maduro.
Jun 24, 2026
De-escalating
Other
7.1-Magnitude Earthquake Strikes Central Venezuela
A 7.1-magnitude earthquake struck central Venezuela with an epicenter near Montalbán in Carabobo state, shaking buildings and knocking out electricity in Caracas and other areas.
Jun 17, 2026
Escalating
Cyber
Construction of New Antenna Array Completed at Bejucal SIGINT Site in Cuba
New commercial satellite imagery shows completed construction of a large circularly disposed antenna array at the Bejucal signals-intelligence site near Havana, one of several Cuban SIGINT facilities CSIS has linked to possible Chinese support.
Jun 2, 2026
Mixed
Sanctions
Russia Delivers Oil to Cuba Amid US Blockade Reversal Signal
A Russian tanker, the Anatoly Kolodkin, delivered approximately 100,000 tonnes of crude oil to Cuba's Matanzas terminal, breaking a de facto US fuel blockade imposed since January 2026.
May 13, 2026
Escalating
Military
U.S. Escalates Visible Surveillance Campaign Against Cuba
U.S. Navy and Air Force assets — including P-8 maritime patrol aircraft, RC-135 Rivet Joint electronic-eavesdropping planes
May 10, 2026
De-escalating
Political
Venezuelan Diaspora Non-Return Following Maduro Capture
Following the U.S. capture of Nicolás Maduro in January 2026, no quantifiable spike in Venezuelan migrant returns has materialized.
Apr 19, 2026
Escalating
Political
Delcy Rodríguez Purges Maduro Network Under U.S. Backing
Following Nicolás Maduro's January removal, Delcy Rodríguez has replaced ministers, military commanders and diplomats while detaining or sidelining businessmen and relatives tied to the former regime.
Apr 11, 2026
Escalating
Institutional
United States Establishes State Department Humanitarian Bureau After USAID Dissolution
Following the dissolution of USAID, the United States created a Bureau of Disaster and Humanitarian Response within the State Department to retain some emergency assistance capability.
Apr 3, 2026
Escalating
Other
Trump Administration Unveils FY2027 $1.5 Trillion Defense Budget Request
The Office of Management and Budget released a FY2027 request seeking $1.15 trillion in national defense discretionary funding plus $350 billion through reconciliation, producing the largest single-year U.S. defense request since World War II.
Mar 30, 2026
Escalating
Sanctions
Russia Delivers Sanctioned Oil Tanker Cargo to Cuba Amid U.S. Blockade
Russia deployed the sanctioned tanker Anatoly Kolodkin to deliver 730,000 barrels of crude to Cuba, the first shipment since Venezuela's supply chain collapsed following the U.S. seizure of Nicolas Maduro in January 2026.
Mar 28, 2026
Mixed
Institutional
Castro Dynasty Reasserts Control During U.S.-Cuba Negotiations
Amid a U.S. oil blockade and secret negotiations with the Trump administration, multiple Castro family members have resurfaced in prominent official roles: Raúl Guillermo Rodríguez Castro (Raúlito) as a back-channel messenger to U.S. officials, Alejandro Castro Espín as a lead negotiator, and Óscar Pérez-Oliva Fraga as the public face of Cuba's new exile investment policy.
Feb 15, 2026
Mixed
Sanctions
Russian Oil Tanker Delivers First Shipment to Cuba Since January
A Russian tanker delivered the first oil shipment to Cuba since January 2026, ending a period of acute energy deprivation triggered by the US seizure of Venezuelan President Nicolás Maduro.
Jan 1, 2026
Mixed
Diplomatic
Pope Leo XIV Publicly Challenges U.S. War Policy and Iran Military Campaign
Pope Leo XIV, beginning in January 2026, issued a sustained series of public challenges to U.S. foreign policy — including the war on Iran, deportation of Catholic immigrants, and dismissal of multilateral institutions — through papal addresses, encyclicals, and diplomatic channels.
Jan 1, 2026
Mixed
Military
Russia Breaks U.S. Naval Blockade of Cuba via Fuel Tanker Dispatch
Russia dispatched the tanker Anatoly Kolodkin to Cuba under a humanitarian fuel aid framing, directly testing the U.S. de facto naval blockade imposed as part of the Trump administration's broader coercive campaign against Havana.
Aug 4, 2025
Escalating
Diplomatic
United States Expands Third-Country Deportation Deals
The United States has made third-country deportation agreements a cross-government diplomatic priority, offering financial transfers, sanctions relief, visa flexibility and reputational concessions to states willing to accept migrants who are not their nationals.
Jul 18, 2025
De-escalating
Legal
U.S. Federal Indictment of Raúl Castro for Murder
The United States Department of Justice issued a federal murder indictment against Cuban President Raúl Castro, replicating the legal coercion strategy previously deployed against Venezuelan President Nicolás Maduro.
Jul 18, 2025
De-escalating
Legal
Trump Administration Prepares Criminal Prosecution of Raúl Castro
The Trump administration intends to bring criminal charges against Raúl Castro, the former Cuban head of state and revolutionary figurehead, now nearly 95 years old and holding no formal office.
Jul 17, 2025
Mixed
Sanctions
Russia Deploys Sanctioned Tankers to Break U.S. Fuel Blockade of Cuba
Russia is actively circumventing U.S. sanctions by dispatching sanctioned tankers to supply Cuba with oil amid a U.S.-imposed fuel blockade that has produced widespread blackouts.
Jul 16, 2025
Escalating
Legal
Federal Grand Jury Indicts Raúl Castro for 1996 Shootdown of U.S. Civilian Aircraft
A federal grand jury in Florida indicted 94-year-old former Cuban President Raúl Castro on charges of murder and conspiracy to kill U.S. nationals for ordering the 1996 shootdown of two civilian aircraft, killing three U.S. citizens and one permanent resident.
Jul 16, 2025
De-escalating
Legal
US Federal Charges Filed Against Raúl Castro Over 1996 Brothers to the Rescue Shootdown
The United States charged former Cuban leader Raúl Castro and five co-defendants with conspiracy to kill US nationals, stemming from Cuba's 1996 military shootdown of two civilian aircraft operated by the Cuban-American group Brothers to the Rescue, which killed four people including three US citizens.
Jul 13, 2025
De-escalating
Cyber
US Intelligence Report Alleges Cuban Attack Drone Acquisition as Intervention Pretext
US classified intelligence, leaked to Axios, alleges Cuba has acquired 300 attack drones — reportedly Iranian-supplied — and is considering strikes on Guantanamo Bay, US naval vessels, and Key West.
Jul 10, 2025
Mixed
Sanctions
Russia Dispatches Second Oil Tanker to Cuba Under US Fuel Blockade
Russia announced a second oil tanker bound for Cuba days after the first Russian-flagged vessel delivered approximately 700,000 barrels of crude — the first significant oil delivery to the island in three months.
Jul 1, 2025
De-escalating
Legal
U.S. Federal Indictment of Raúl Castro on Murder Charges
The U.S. Department of Justice indicted former Cuban President Raúl Castro on charges of murder and conspiracy related to the 1996 Cuban Air Force shootdown of two Brothers to the Rescue aircraft
Jul 1, 2025
De-escalating
Sanctions
Cuba Oil Reserve Exhaustion Following Venezuelan Supply Cutoff
Cuba's government confirmed its oil reserves have been fully depleted, a direct consequence of the Trump administration severing Venezuelan oil shipments to Havana following the collapse of the Maduro-aligned government in Caracas.
Jun 10, 2025
Escalating
Diplomatic
Hegseth Visit to Guantanamo Bay Naval Station
U.S. Defense Secretary Pete Hegseth flew to Guantanamo Bay Naval Station, the second high-profile U.S. military visit in under two weeks.
Jun 4, 2025
De-escalating
Sanctions
U.S. Treasury Sanctions Cuban President Diaz-Canel and Military Ministry
The U.S. Treasury Department designated Cuban President Miguel Diaz-Canel, four affiliated individuals, and five entities — including the Ministry of the Revolutionary Armed Forces — under sanctions authority.
Jun 4, 2025
De-escalating
Sanctions
U.S. Secondary Sanctions Force Mass Foreign Business Exodus from Cuba
U.S. secondary sanctions targeting GAESA, Cuba's military conglomerate controlling roughly half the national economy, triggered the withdrawal of Iberostar (12 hotels), Meliá (15 hotels), Blue Diamond (dozens of hotels), Archipelago International, and a Visa/Mastercard processing bank.
May 29, 2025
De-escalating
Sanctions
U.S. Blocks Vanguard Energy-Cuba Fuel Deal and Sanctions Cupet
The State Department halted a 250,000-barrel fuel shipment from Vanguard Energy to Cuba, declaring no license had been issued for the transaction.
May 23, 2025
Escalating
Sanctions
US Escalates Multi-Vector Pressure Campaign Against Cuba
The United States has simultaneously deployed an oil blockade, targeted sanctions on senior Cuban officials, military surveillance flights near Cuban airspace, and a federal murder indictment against former President Raúl Castro — the symbolic apex of Cuba's revolutionary hierarchy.
May 23, 2025
Escalating
Institutional
Trump Administration Staffing of Federal Security Agencies with Loyalty-Based Appointments
The Trump administration is restructuring federal law enforcement agencies — particularly ICE and the FBI — by prioritizing political loyalty over professional qualification, mirroring a documented autocratic staffing pattern.
May 22, 2025
De-escalating
Diplomatic
CIA Director Ratcliffe Delivers Regime-Change Ultimatum to Havana
CIA Director John Ratcliffe traveled to Havana to personally deliver a Trump administration ultimatum demanding 'fundamental changes' in exchange for economic and security engagement.
May 21, 2025
Escalating
Diplomatic
Russia Reaffirms Cuba Solidarity After U.S. Charges Against Raúl Castro
Russia's Foreign Ministry publicly pledged 'most active support' to Cuba following U.S. murder charges against former President Raúl Castro, framing the charges as illegal interference and sanctions escalation.
May 21, 2025
De-escalating
Legal
U.S. Indicts Former Cuban President Raúl Castro
The U.S. Justice Department filed criminal charges against former Cuban President Raúl Castro for murder and conspiracy to kill U.S. citizens, tied to Cuba's 1996 shootdown of two Brothers to the Rescue civilian aircraft.
May 20, 2025
De-escalating
Legal
DOJ Indictment of Raúl Castro for 1996 Brothers to the Rescue Shootdown
The US Department of Justice unsealed a federal indictment against former Cuban President Raúl Castro, charging him with conspiracy to murder US nationals, destruction of aircraft, and murder in connection with the 1996 Cuban Air Force shootdown of two Brothers to the Rescue planes.
May 20, 2025
De-escalating
Diplomatic
Cuba-U.S. Diplomatic Standoff Amid Escalating U.S. Pressure Campaign
Cuba's UN ambassador granted a rare on-the-record interview signaling openness to broad negotiations while publicly rejecting U.S. good faith, as the Trump administration simultaneously escalated its coercive campaign through an oil blockade, criminal charges against Raúl Castro, and CIA Director Ratcliffe's direct demands in Havana.
May 14, 2025
De-escalating
Diplomatic
CIA Director Ratcliffe Delivers Conditional Engagement Ultimatum to Cuba
CIA Director John Ratcliffe traveled to Havana to deliver a direct message from President Trump that the U.S. would engage seriously on economic and security issues only if Cuba undertakes fundamental changes.
May 14, 2025
De-escalating
Sanctions
US Reiterates $100M Cuba Aid Offer Amid Fuel Crisis and Expanded Sanctions
The US State Department repeated a $100m humanitarian aid offer to Cuba conditioned on 'meaningful reforms to Cuba's communist system,' while simultaneously maintaining a sanctions regime that has severed Cuba's fuel supply chain.
May 7, 2025
De-escalating
Sanctions
Russian Fuel Tanker Diverts Away from Cuba Under U.S. Blockade Pressure
A Russian tanker carrying 242,000 barrels of diesel turned away from Cuba and redirected toward South America, denying the island a critical fuel lifeline.
May 1, 2025
De-escalating
Sanctions
U.S. Maximum Pressure Campaign Against Cuba Escalates to Ultimatum Phase
The Trump administration escalated its coercive campaign against Cuba through a May 1 executive order authorizing secondary sanctions on foreign firms operating in Cuban strategic sectors, a CIA director visit to Havana delivering a security ultimatum, and a federal indictment of Raúl Castro.
May 1, 2025
De-escalating
Sanctions
U.S. Oil Blockade and Pressure Campaign Against Cuba Intensifies
The Trump administration has imposed an oil blockade on Cuba, producing near-total electricity and fuel collapse across the island — residents in Camagüey report two to three hours of electricity per day.
Apr 28, 2025
Escalating
Alliance
Russia-Nicaragua Military Cooperation Agreement Ratified
Russia's Federation Council ratified a military cooperation agreement with Nicaragua, formalizing a framework initially signed in Moscow in September 2024.
Apr 24, 2025
De-escalating
Sanctions
U.S. Sanctions GAESA and CIA Director Visits Cuba Amid Coordinated Pressure Campaign
The Trump administration launched a multi-vector pressure campaign against Cuba: an executive order expanding sanctions to target GAESA, the military conglomerate controlling an estimated three times Cuba's state budget; a CIA director visit demanding economic and security concessions; and federal prosecutors pursuing a drug trafficking indictment against Raúl Castro.
Apr 23, 2025
Escalating
Military
USS Nimitz Carrier Strike Group Deployed to Southern Caribbean as Cuba Pressure Campaign
The USS Nimitz carrier strike group entered the southern Caribbean on the same day the DOJ announced charges against Raúl Castro, a deliberate coordination of legal and military pressure against Cuba.
Apr 20, 2025
De-escalating
Sanctions
Post-Maduro Venezuela: U.S. Oil Deal Fails to Translate into Broad Economic Recovery
Following the U.S. capture of Nicolás Maduro in January 2025, the Trump administration began selling Venezuelan oil and remitting proceeds to Caracas, promising transparent reinvestment for the Venezuelan people.
Apr 19, 2025
Escalating
Diplomatic
United States Opens Coercive Humanitarian Negotiations with Cuba
A senior U.S. delegation traveled to Havana to press Cuba's government to accept economic liberalization, political concessions, and expanded U.S. access under conditions created by tightened fuel pressure.
Apr 18, 2025
De-escalating
Diplomatic
Cuba Attempts Direct Back-Channel Outreach to Trump
A senior figure in Raúl Castro's inner circle reportedly attempted to send President Trump a sealed message through a private courier rather than formal diplomatic channels.
Apr 17, 2025
Escalating
Diplomatic
Cuba Announces Release of 2,010 Prisoners Under US Coercive Pressure
Cuba's Communist government announced the release of 2,010 prisoners, framed domestically as a sovereign Holy Week gesture but occurring under direct US economic coercion including a near-total oil blockade.
Apr 10, 2025
Mixed
Political
Rodríguez Consolidates Post-Maduro Authority in Venezuela
Following Maduro's January 2025 capture by US special forces, Delcy Rodríguez has moved to consolidate power through symbolic de-Chavezification, selective prisoner releases, an amnesty law, and cabinet restructuring.
Apr 9, 2025
De-escalating
Sanctions
U.S. Fuel Blockade Intensifies Cuba's Systemic Breakdown Risk
The United States imposed and enforced a fuel blockade on Cuba by halting Venezuelan oil shipments and threatening other suppliers, sharply constraining the island's energy base.
Apr 7, 2025
Mixed
Sanctions
Trump Grants Humanitarian Exemption for Russian Oil Delivery to Cuba
The Trump administration granted a case-by-case exemption allowing a sanctioned Russian tanker to deliver 730,000 barrels of crude to Cuba, the first oil shipment to the island since January.
Apr 7, 2025
Escalating
Cyber
Rubio Denies US Culpability for Cuba Humanitarian Crisis Amid Escalating Pressure Campaign
Secretary Rubio publicly denied that US actions constitute punitive pressure on Cuba, framing the island's fuel collapse as a pre-existing governance failure.
Apr 1, 2025
Escalating
Diplomatic
PRC Green Energy Expansion Across Caribbean Basin
Between 2020 and 2025, Chinese green technology exports to the Caribbean grew over 570 percent to $280 million annually across 13 countries, with solar parks, electric bus fleets, microgrids, and technician training programs deployed across Barbados, Jamaica, Guyana, Suriname, and Cuba.
Apr 1, 2025
Mixed
Sanctions
Russia Delivers Humanitarian Oil Shipment to Cuba Amid US Pressure Campaign
Russia delivered 100,000 tons of oil to Cuba via the tanker Anatoly Kolodkin, framed as humanitarian cargo under international maritime law protections.
Apr 1, 2025
Mixed
Sanctions
Sanctioned Russian Tanker Delivers Crude Oil to Cuba Amid US Blockade
The Anatoly Kolodkin, a sanctioned Russian crude tanker, docked at Matanzas, Cuba, delivering 730,000 barrels — the first crude shipment since Venezuela's Maduro was removed, severing Cuba's primary energy lifeline.
Mar 31, 2025
Escalating
Military
U.S. Consolidates Post-Maduro Control Over Venezuela, Signals Cuba Pressure Campaign
Following the January U.S. military seizure of Venezuelan President Maduro — explicitly ordered by Trump — Washington has installed de facto oversight over Venezuelan governance through Maduro's former VP Delcy Rodriguez.
Mar 30, 2025
De-escalating
Sanctions
Trump Administration Permits Sanctioned Russian Tanker to Deliver Oil to Cuba
The Trump administration allowed a sanctioned Russian tanker carrying 100,000 metric tons of crude oil to deliver fuel to Cuba, citing humanitarian grounds, while officially denying any formal policy change.
Mar 30, 2025
Mixed
Sanctions
Sanctioned Russian Tanker Breaches U.S. Oil Blockade on Cuba
The sanctioned Russian-flagged vessel Anatoly Kolodkin entered Cuban waters carrying approximately 700,000 barrels of Russian Urals crude, ending a three-month oil supply vacuum caused by U.S. coercive pressure on Venezuela, Mexico, and other suppliers.
Mar 27, 2025
Mixed
Alliance
U.S. Builds Coercive Pressure Architecture Across Latin America via 'Shield of the Americas' Framework
The Trump administration is systematically constructing a coercive regional architecture in Latin America combining terrorist designations, joint military operations, and political realignment through selective multilateral forums.
Mar 25, 2025
Escalating
Sanctions
Russia Launches Fertiliser Diplomacy Amid Hormuz Disruption
Russia signaled readiness to redirect fertiliser exports to global south markets as Hormuz disruption raised fears of supply shocks, while linking access to support for Russian-led groupings and using the crisis to press for sanctions relief in the West.
Mar 5, 2025
Mixed
Other
FBI Deployment to Cuba for Speedboat Shootout Investigation
An FBI technical team deployed to Cuba to independently investigate a February 25 armed incursion in which five Cuban nationals were killed in a firefight with Cuban border guards.
Feb 18, 2025
Mixed
Sanctions
Russian Tanker Breaks US Oil Blockade on Cuba
The Anatoly Kolodkin, a Russian-owned tanker, docked at Matanzas port carrying approximately 730,000 barrels of crude oil, marking the first crude shipment to Cuba since early January 2025.
Feb 18, 2025
Mixed
Sanctions
Russia Delivers Oil to Cuba Under US Humanitarian Exemption
A sanctioned Russian tanker, the Anatoly Kolodkin, delivered approximately 700,000 barrels of crude oil to Matanzas, Cuba — the island's first shipment since January 9.
Feb 6, 2025
Mixed
Sanctions
Russia Dispatches Second Oil Tanker to Cuba Under US Fuel Blockade
Russia is loading a second oil tanker bound for Cuba after a US-imposed fuel blockade severed the island's supply chain following Venezuela's political collapse.
Feb 4, 2025
Escalating
Military
U.S. Military Intensifies Surveillance Flights Over Cuba
U.S. Navy surveillance aircraft based at NAS Jacksonville have conducted over 150 hours of ISR flights over Cuba since February 4, 2025, representing a significant concentration of intelligence collection activity against the island.
Jan 3, 2025
Mixed
Military
U.S. Capture of Maduro and Venezuelan Regime Co-optation
The United States conducted a covert military operation on January 3, capturing Venezuelan President Nicolás Maduro and replacing him with Vice President Delcy Rodríguez, converting Venezuela from a regional adversary into what the Trump administration frames as a compliant vassal state.
Jan 1, 2025
De-escalating
Diplomatic
Cuban Migration Redirects to Latin America Under U.S. Maximum Pressure
Since January 2025, the Trump administration's maximum pressure campaign against Cuba — including travel restrictions, visa freezes, termination of humanitarian parole, and an oil embargo — has reduced irregular Cuban border encounters with the U.S. by 99 percent while redirecting Cuban emigration to Brazil, Mexico, and Uruguay.
Jan 1, 2025
De-escalating
Legal
U.S. Federal Prosecutors Move Toward Raúl Castro Indictment Over 1996 Shootdown
Miami federal prosecutors are advancing toward a criminal indictment of Raúl Castro, Cuba's former president and current power broker, for his role as defense minister in ordering the 1996 shootdown of two Brothers to the Rescue Cessnas that killed four people, including three U.S. citizens.
Jan 1, 2025
De-escalating
Diplomatic
CIA Director Ratcliffe Visits Havana for Intelligence-Level Talks
CIA Director John Ratcliffe traveled to Havana for a direct meeting with Cuba's interior minister and intelligence chief — a rare and high-signal channel activation at the intelligence-to-intelligence level.
Jan 1, 2025
Unclear
Diplomatic
Trump Administration Signals Coercive Escalation Toward Cuba
President Trump declared 'Cuba is next,' signaling that the administration intends to apply coercive pressure on Havana following other foreign policy actions.
Jan 1, 2025
Mixed
Sanctions
US Grants Humanitarian Exemption for Sanctioned Russian Tanker to Deliver Oil to Cuba
The Trump administration permitted the sanctioned Russian Aframax tanker Anatoly Kolodkin to deliver 730,000 barrels of Urals crude to Cuba's Bay of Matanzas, ending a three-month oil supply gap.
Oct 1, 2024
De-escalating
Sanctions
Cuba Total Fuel Reserve Depletion and Nationwide Blackouts
Cuba's government confirmed complete depletion of fuel oil and diesel reserves, triggering nationwide blackouts and street protests lasting at least three days.
Apr 19, 2021
Stable
Political
Díaz-Canel Replaces Raúl Castro as Cuban Communist Party First Secretary
Miguel Díaz-Canel was elected First Secretary of the Cuban Communist Party at a party congress coinciding with the 60th anniversary of the Bay of Pigs defeat, formally ending over six decades of Castro-family rule.
Date unknown
De-escalating
Political
Deadly Earthquakes Strain Venezuela's U.S.-Backed Transition
Deadly earthquakes struck Venezuela, forcing newly installed president Delcy Rodriguez to declare a state of emergency while managing a fragile transition.
Date unknown
De-escalating
Institutional
Cuba Announces 176-Measure Economic Overhaul Loosening State Control
Cuba rushed through 176 measures expanding private enterprise, permitting private banks, multiple business ownership, and the sale of state assets to foreign and Cuban-emigre buyers, the first relinquishment of full commercial control since the 1959 revolution.
Date unknown
Stable
Political
Death of Cuban Security Architect Ramiro Valdes Menendez
Ramiro Valdes Menendez, founder of Cuba's Interior Ministry and architect of its Soviet-modeled surveillance and internal-security apparatus, died at 94.
Date unknown
De-escalating
Sanctions
U.S. Oil Blockade Collapses Cuban Education System
A Trump administration executive order prohibiting countries from delivering oil to Cuba has starved the island of fuel, halting transport and forcing schools onto half-days, remote learning, and an early end to the academic year.
Date unknown
De-escalating
Sanctions
US Pressure Pushes Cuba Toward a Breaking Point
The Trump administration has indicted senior Cuban officials and sanctioned the state oil company and military-linked entities that dominate Cuba's economy.
Date unknown
Escalating
Other
Proposal to Update Venezuela Democratic Transition Framework Post-Maduro
A working paper proposes updating the 2020 U.S. Democratic Transition Framework to guide a negotiated transition in Venezuela after Maduro's January 2026 capture and Washington's recognition of Delcy Rodriguez's interim government.
Date unknown
De-escalating
Sanctions
Trump Administration Escalates Multi-Instrument Pressure Campaign Against Cuba
The Trump administration has launched its most assertive Cuba policy in recent memory, combining criminal indictments of senior officials including Raúl Castro, new sanctions on regime leaders and state entities, expanded military and intelligence activity in the Caribbean, and high-level visits to Guantanamo Bay.
Date unknown
De-escalating
Other
Cuba Survival Economy Sustained by Miami Diaspora Cargo Flows
Cuban travelers departing Miami International Airport routinely carry suitcases packed with essential goods — food, medicine, hardware supplies — that are unavailable or unaffordable inside Cuba.
Date unknown
De-escalating
Diplomatic
Trump Administration Signals Possible Forceful Action Against Cuba
President Trump has publicly stated he will have the 'honor of taking Cuba,' and the administration has not ruled out military action following recent interventions in Venezuela and Iran.
Date unknown
De-escalating
Sanctions
International Business Exodus from Cuba Under U.S. Pressure
International firms are exiting Cuba as the Trump administration escalates economic pressure, accelerating the island's economic deterioration.
Date unknown
De-escalating
Diplomatic
China's Latin America Economic-to-Geopolitical Influence Gap Widens
Across multiple Latin American states — Panama, Venezuela, Cuba, Nicaragua, and Honduras — China's substantial economic footprint has failed to produce durable political alignment, as governments recalibrate toward Washington under domestic pressure and U.S. strategic competition.
Date unknown
Mixed
Diplomatic
Trump Second-Term Latin America Policy Posture Takes Shape
The incoming Trump administration is orienting its Latin America policy around three coercive levers — tariffs, sanctions, and potential limited military action — to extract cooperation on migration, fentanyl interdiction, and Chinese infrastructure exclusion.
Date unknown
De-escalating
Sanctions
Cuba Sanitation Collapse Amid Fuel Cutoff and Structural Economic Failure
Havana's sanitation infrastructure has effectively collapsed, with only 44 of 106 sanitation trucks operational and garbage accumulations reaching half a block in length in dense urban neighborhoods.
Date unknown
Stable
Political
Cuba Holds Approximately 1,200 Political Prisoners Amid U.S. Pressure
Cuba's communist government holds approximately 1,200 political prisoners, including dissident performance artist Luis Manuel Otero and an unnamed close collaborator.
Date unknown
De-escalating
Sanctions
Cuba Tourism Collapse Under U.S. Pressure Campaign
International arrivals to Cuba fell 48% in Q1 year-on-year, representing a severe contraction in the regime's primary hard-currency revenue stream.
Date unknown
Mixed
Political
U.S. Midterm Elections Forecast: Latin America Policy Implications
The November 2025 U.S. midterm elections present the most likely near-term structural check on the Trump administration's Latin America agenda, which has been defined by military boat strikes, mass deportations, tariffs, and Monroe Doctrine reassertion.
Simmering / Americas
Twin earthquakes expose Venezuela's hollowed state capacity as Washington deepens its protectorate grip over the transition.
Simmering / Americas
Venezuela rejected ICJ jurisdiction ahead of a binding Essequibo ruling while operating as a US-dependent client state.