1990s – Cuba endures the “Special Period,” a severe economic contraction after the Soviet Union collapses, a backdrop that resurfaces as fuel shortages re‑emerge in 2026 [14].

2015 – The United States restores diplomatic relations with Cuba, sparking a tourism boom and classic‑car tours that later vanish amid the 2026 energy crisis [3].

Late 2024 – Cuba experiences five nationwide blackouts, a pattern that intensifies after Venezuela halts oil shipments in early 2026 [20].

Jan 3, 2026 – U.S. forces raid Caracas, capture Nicolás Maduro and his wife, and kill 32 Cuban security personnel, cutting off a major source of subsidized Venezuelan oil to Havana [1].

Jan 11, 2026 – President Donald Trump posts that “there will be no more oil or money going to Cuba” and warns the island is “very close to failing,” linking the threat to the Maduro capture [9][1].

Jan 12, 2026 – Cuban President Miguel Díaz‑Canel tweets “No one dictates what we do,” rejecting Trump’s ultimatum and asserting Cuban sovereignty [6].

Jan 12, 2026 – Díaz‑Canel announces Cuba is “open to serious dialogue on sovereign equality, mutual respect and international law,” while noting no talks exist beyond migration issues [8].

Jan 12, 2026 – China’s foreign ministry calls on the United States to lift the blockade and sanctions on Cuba, framing U.S. actions as counter‑productive [8].

Jan 12, 2026 – Cuba’s foreign ministry states there are “no talks with the United States” beyond migration, emphasizing conditions of sovereign equality [17].

Jan 28, 2026 – Trump tells reporters in Iowa that Cuba will “fail pretty soon” and urges Havana to strike a deal before it is “too late,” emphasizing an imminent economic collapse [7].

Jan 29, 2026 – U.S. diplomats warn “nothing is getting in” and that “no more oil is coming” to Cuba, and the White House mulls the first naval blockade of the island since 1962 [5].

Jan 30, 2026 – Trump signs an executive order imposing tariffs on any goods from nations that supply oil to Cuba, targeting Mexico as the primary source of remaining shipments [15].

Jan 30, 2026 – U.S. policy shifts, including the tariff order, threaten to cripple Cuba’s oil supply, prompting officials to label the regime “tottering” after 67 years [13].

Jan 30, 2026 – Cuban activists report mass torch‑march protests and growing unrest, while citizens adopt solar power and farming to survive the deepening shortages [14].

Jan 31, 2026 – Deputy Secretary of State Christopher Landau publicly denounces the “Castro regime” as failing, and Secretary of State Marco Rubio calls for a “change in dynamic” with Cuba [13].

Feb 1, 2026 – On Air Force One, Trump declares the United States “is starting to talk to Cuba,” though he gives no details on timing or substance [12].

Feb 1, 2026 – Mexican President Claudia Sheinbaum pledges to send humanitarian food aid to Cuba within days, despite U.S. pressure to halt oil shipments [11].

Feb 4, 2026 – A fault at the Holguín 220 kV substation triggers a massive outage, darkening eastern Cuba’s provinces and highlighting the island’s fragile grid after years of blackouts [20].

Feb 4, 2026 – UN Secretary‑General Antonio Guterres warns the power failure could precipitate a humanitarian collapse if U.S. tariff decree proceeds [20].

Feb 5, 2026 – Deputy Foreign Minister Carlos Fernández de Cossío says Cuba is ready for “meaningful” dialogue but will not discuss its constitutional system, rejecting U.S. regime‑change demands [4].

Feb 5, 2026 – The U.S. tariff decree on oil‑related goods threatens further deterioration of Cuba’s energy crisis, as analysts link the measure to the recent eastern blackout [20].

Feb 14, 2026 – Mexico launches a nationwide drive, collecting food and medicine for Cuba; volunteers pack supplies in a white tent on the Zócalo and ship them nightly by navy trucks [19].

Feb 18, 2026 – Cuba’s economy crumbles under the U.S. oil cutoff and a collapse in tourism, forcing school closures, hotel shutdowns and a surge in self‑sufficiency measures [3].

Feb 18, 2026 – Cuban Foreign Minister Bruno Rodríguez meets Russian Foreign Minister Sergey Lavrov and President Vladimir Putin in Moscow; Lavrov urges the U.S. to abandon blockade plans and Putin pledges continued Russian support for Cuba [10].

Feb 24, 2026 – Canada announces it is formulating an assistance plan for Cuba amid a deepening fuel crisis, while the United Nations warns that unmet energy needs could trigger a full‑scale humanitarian disaster [2].

Feb 24, 2026 – The UN human‑rights office declares the U.S. raid that captured Maduro illegal, labeling it a violation of international law [2].