Oct 1962 – The United States and the Soviet Union confront each other in the Cuban Missile Crisis, the last major Cold‑War showdown over Cuba, a benchmark the Trump administration cites when warning of a possible naval blockade. [3]

Early 19th century – The Monroe Doctrine is invoked by the Trump administration to justify a new “Donroe Doctrine” that seeks to dominate the Western Hemisphere and pressure Cuba and its allies. [5]

Jan 3, 2026 – U.S. special‑operations forces capture Venezuelan President Nicolás Maduro and his wife in a Caracas raid, killing 32 Cuban security personnel who were protecting Maduro; the operation marks the deadliest U.S.–Cuban clash since the Cold War. [1][9]

Jan 5, 2026 – Senator Lindsey Graham warns Cuba aboard Air Force One that “you just wait for Cuba,” while President Trump denounces Colombian President Petro and demands “total access” from Venezuela’s Delcy Rodríguez, signaling a hardening U.S. stance toward Havana. [9]

Jan 5, 2026 – President Miguel Díaz‑Canel protests outside the U.S. Embassy, declares national mourning for the 32 Cuban casualties, and vows to defend the Venezuela‑Cuba alliance, underscoring Cuba’s perception of an existential threat. [5]

Jan 11, 2026 – Trump posts on Truth Social that there will be “no more oil or money” flowing to Cuba and urges Havana to “strike a deal before it is too late,” tying the ultimatum directly to the recent Maduro capture. [1][8][12]

Jan 12, 2026 – Díaz‑Canel tweets that Cuba is “open to serious dialogue” based on sovereign equality, yet later that day reasserts “no one dictates what we do,” rejecting any U.S.–imposed deal and emphasizing sovereignty. [7][11]

Jan 12, 2026 – Foreign Minister Bruno Rodríguez Parrilla declares Cuba’s absolute right to import fuel from any willing exporter and dismisses U.S. claims that Cuba traded security services for Venezuelan oil, framing Washington’s actions as criminal. [4]

Jan 28, 2026 – In Iowa, Trump tells reporters Cuba is “very close to failing” and warns of imminent economic collapse unless Havana negotiates, while Cuban ambassador Carlos de Cespedes calls the U.S. oil blockade “international piracy.” [6]

Jan 29, 2026 – U.S. diplomats in Havana warn staff that “nothing is getting in” and that the White House is considering the first naval blockade of Cuba since 1962, while Mexico’s President Claudia Sheinbaum announces Mexico will hold back a planned oil shipment to the island. [3]

Jan 29, 2026 – Energy analyst Jorge Piñón tells CNN that a full “oil valve” shutdown will trigger Cuba’s economic collapse, likening the scenario to an approaching hurricane. [3]

Jan 29, 2026 – Cuban state TV shows President Díaz‑Canel overseeing tank and helicopter drills, urging citizens to prepare for a “countrywide war” against imperialist aggression. [3]

Feb 1, 2026 – On Air Force One, Trump announces the United States “is starting to talk to Cuba” but provides no details; the administration simultaneously issues an executive order that tariffs any goods from nations exporting oil to Cuba, targeting Mexico’s shipments. [10]

Feb 1, 2026 – Mexican President Sheinbaum warns the new tariff could spark a humanitarian crisis in Cuba and says Mexico will seek alternative ways to assist the island. [10]

Feb 5, 2026 – Deputy Foreign Minister Carlos Fernández de Cossío tells CNN that Cuba is ready for “meaningful” dialogue but will not discuss its constitutional system, rejecting U.S. calls for regime change and blaming sanctions for blackouts and fuel shortages. [2]

Feb 5, 2026 – The Trump administration continues to threaten tariffs on nations exporting oil to Cuba and links any relief to the return of property confiscated from Cuban exiles after the 1959 revolution, outlining a conditional path toward easing the embargo. [2][1]