{"id":809,"date":"2026-05-20T19:04:32","date_gmt":"2026-05-20T19:04:32","guid":{"rendered":"https:\/\/bostonrelocationinsider.com\/?p=809"},"modified":"2026-05-20T19:04:32","modified_gmt":"2026-05-20T19:04:32","slug":"timeline-of-recent-us-cuba-relations-amid-heightened-tensions-in-trumps-second-term","status":"publish","type":"post","link":"https:\/\/bostonrelocationinsider.com\/?p=809","title":{"rendered":"Timeline of recent US-Cuba relations amid heightened tensions in Trump\u2019s second term"},"content":{"rendered":"<article>\n<div>\n<p><span>WASHINGTON (AP) \u2014 Wednesday\u2019s U.S. indictment of former Cuban President Ra\u00fal Castro is the latest salvo in the Trump administration\u2019s months-long pressure campaign against the Caribbean island\u2019s socialist-controlled government.<\/span><\/p>\n<p>Read more <a href=\"https:\/\/bostonrelocationinsider.com\/?p=807\">Pawtucket will extend school day and year to make up for shortfall in learning time<\/a><\/p>\n<p><span>Castro was charged for his alleged role in the 1996 shootdown of two planes operated by the Miami-based exile group Brothers to the Rescue. Castro was defense minister at the time.<\/span><\/p>\n<p><span>President Donald Trump has been escalating talk on regime change in Cuba after the military action in Venezuela early this year resulted in the capture of President Nicol\u00e1s Maduro. In addition, a White House-ordered economic blockade has led to blackouts, food shortages and a collapse in economic activity across Cuba.<\/span><\/p>\n<\/div>\n<div>\n<p><span>The indictment comes amid rising tensions between Trump\u2019s administration and Cuba\u2019s government. Meanwhile, the U.S. is in the midst of an uneasy ceasefire in the U.S. war against Iran.<\/span><\/p>\n<div>\n<div>\n<div><span>Get Starting Point<\/span><\/div>\n<div><span>A guide through the most important stories of the morning, delivered Monday through Friday.<\/span><\/div>\n<div>\n<div><label>Enter Email<\/label><\/p>\n<div><button>Sign Up<\/button><\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<p><span>Here\u2019s a closer look at developments over the year between Cuba and the U.S.<\/span><\/p>\n<div>\n<div>\n<h3>Jan. 4<\/h3>\n<\/div>\n<\/div>\n<p><span>A day after the operation in Venezuela that captured Maduro, Secretary of State Marco Rubio declared Cuba\u2019s government was \u201cin a lot of trouble,\u201d as the president renewed calls for an American takeover of the Danish territory of Greenland.<\/span><\/p>\n<div>\n<div>\n<h3>Jan. 11 <\/h3>\n<\/div>\n<\/div>\n<p><span>Trump fired off a warning to the government of Cuba as the close ally of Venezuela braced for potential unrest after Maduro was deposed. Trump called for the Cuban government \u201cto make a deal BEFORE IT IS TOO LATE.\u201d<\/span><\/p>\n<p><span>Cuba\u2019s president, Miguel D\u00edaz-Canel, responded, \u201cThose who turn everything into a business, even human lives, have no moral authority to point the finger at Cuba in any way, absolutely in any way.\u201d<\/span><\/p>\n<div>\n<div>\n<h3>Jan. 30<\/h3>\n<\/div>\n<\/div>\n<p><span>Trump signed an executive order to impose a tariff on any goods from countries that sell or provide oil to Cuba, a move that could further cripple the island.<\/span><\/p>\n<div>\n<div>\n<h3>Feb. 27 <\/h3>\n<\/div>\n<\/div>\n<p><span>A day before the war in Iran began, Trump said the U.S. was in talks with Havana and raised the possibility of a \u201cfriendly takeover of Cuba,\u201d though he didn\u2019t offer any details.<\/span><\/p>\n<p><span>Trump said Rubio was in discussions with Cuban leaders \u201cat a very high level.\u201d<\/span><\/p>\n<p><span>Trump didn\u2019t clarify his comments but seemed to indicate that the situation with Cuba, among Washington\u2019s bitterest adversaries for decades, was coming to a critical point.<\/span><\/p>\n<div>\n<div>\n<h3>Sometime in February <\/h3>\n<\/div>\n<\/div>\n<p><span>Ra\u00fal Guillermo Rodr\u00edguez Castro, the grandson of Castro known as \u201cRa\u00falito,\u201d secretly met with Rubio on the sidelines of a Caribbean Community summit in St. Kitts in February.<\/span><\/p>\n<div>\n<div>\n<h3>March 13<\/h3>\n<\/div>\n<\/div>\n<p><span>D\u00edaz-Canel said Cuba and the U.S. held talks, marking the first time the Caribbean country confirmed widespread speculation about discussions with the Trump administration amid an energy crisis.<\/span><\/p>\n<p><span>He said the talks \u201cwere aimed at finding solutions through dialogue to the bilateral differences between our two nations. International factors facilitated these exchanges.\u201d<\/span><\/p>\n<div>\n<div>\n<h3>March 31<\/h3>\n<\/div>\n<\/div>\n<p><span>A sanctioned Russian oil tanker arrived in Cuba, the first time in three months fuel reached the island.<\/span><\/p>\n<div>\n<div>\n<h3>April 9<\/h3>\n<\/div>\n<\/div>\n<p><span>Diaz-Canel said he would not resign.<\/span><\/p>\n<div>\n<div>\n<h3>April 10<\/h3>\n<\/div>\n<\/div>\n<p><span>Two senior State Department officials \u2014 Jeremy Lewin, who is in charge of all U.S. foreign assistance, and Michael Kozak, the top U.S. diplomat for Latin America \u2014 led a delegation to Havana and met with Rodr\u00edguez Castro, according to one U.S. official familiar with the meetings.<\/span><\/p>\n<div>\n<div>\n<h3>April 12<\/h3>\n<\/div>\n<\/div>\n<p><span>D\u00edaz-Canel said in an interview he would not step down and that the U.S. has no valid reason to carry out a military attack against the island or to attempt to depose him.<\/span><\/p>\n<p><span>Speaking in the interview on NBC\u2019s \u201cMeet the Press,\u201d the president said an invasion of Cuba would be costly and affect regional security.<\/span><\/p>\n<div>\n<div>\n<h3>April 16<\/h3>\n<\/div>\n<\/div>\n<p><span>D\u00edaz-Canel spoke during a rally that drew hundreds of people to commemorate the 65th anniversary of the declaration of the Cuban Revolution\u2019s socialist essence.<\/span><\/p>\n<p><span>\u201cThe moment is extremely challenging and calls upon us once again, as on April 16, 1961, to be ready to confront serious threats, including military aggression. We do not want it, but it is our duty to prepare to avoid it and, if it becomes inevitable, to defeat it,\u201d D\u00edaz-Canel said.<\/span><\/p>\n<p>Read more <a href=\"https:\/\/bostonrelocationinsider.com\/?p=805\">\u2018Giant of American politics\u2019: Markey, Warren, other Mass. politicians remember longtime congressman Barney Frank<\/a><\/p>\n<div>\n<div>\n<h3>April 17<\/h3>\n<\/div>\n<\/div>\n<p><span>News emerged that an American delegation recently met with Cuban government officials, marking a renewed diplomatic push. This was at least the third meeting with Rodr\u00edguez Castro.<\/span><\/p>\n<p><span>A senior State Department official met with Rodr\u00edguez Castro earlier in the month, according to a department official, who was not authorized to comment publicly and spoke on condition of anonymity to discuss the sensitive matter.<\/span><\/p>\n<p><span>The official did not say who from the U.S. met with Rodr\u00edguez Castro, whose grandfather is believed to play an influential role in the Cuban government despite not holding an official post. A second U.S. official said Rubio was not part of the delegation that visited Havana.<\/span><\/p>\n<div>\n<div>\n<h3>April 23<\/h3>\n<\/div>\n<\/div>\n<p><span>A Cuban diplomat speaking at the United Nations said Havana will not abide by any American \u201cultimatums\u201d to release political prisoners as part of new talks.<\/span><\/p>\n<p><span>In an interview with The Associated Press, Cuban Ambassador to the U.N. Ernesto Sober\u00f3n Guzm\u00e1n said internal issues regarding detainees \u201care not on the negotiating table.\u201d The release of political prisoners was a key U.S. demand as the longtime adversaries held discussions in Cuba for the first time in a decade.<\/span><\/p>\n<div>\n<div>\n<h3>April 28 <\/h3>\n<\/div>\n<\/div>\n<p><span>Senate Republicans rejected legislation from Democrats that would have required Trump to end the U.S. energy blockade on Cuba unless he receives approval from Congress.<\/span><\/p>\n<p><span>The vote on the war powers resolution showed how Republicans continue to stand behind Trump as he acts unilaterally to exert American force in a range of global conflicts, including Venezuela, Iran and Cuba \u2014 one of the U.S.\u2019s closest neighbors.<\/span><\/p>\n<div>\n<div>\n<h3>May 7<\/h3>\n<\/div>\n<\/div>\n<p><span>U.S. officials said the United States was not looking at imminent military action against Havana despite Trump\u2019s repeated threats that \u201cCuba is next\u201d and that American warships deployed in the Middle East for the Iran conflict could return by way of the island.<\/span><\/p>\n<p><span>The officials involved in preliminary discussions with Cuban authorities also told the AP that they are not optimistic the communist government will accept an offer for tens of millions of dollars in humanitarian aid, two years of free Starlink internet access for all Cubans, agricultural assistance and infrastructure support.<\/span><\/p>\n<p><span>But they said Cuba had not yet outright refused the offer, which came with conditions that the government has long resisted, even after the Trump administration imposed new sanctions on Havana.<\/span><\/p>\n<div>\n<div>\n<h3>May 14<\/h3>\n<\/div>\n<\/div>\n<p><span>U.S. and Cuban officials said CIA Director John Ratcliffe met with Cuban officials including Ra\u00fal Castro\u2019s grandson during a high-level visit to the island.<\/span><\/p>\n<p><span>Ratcliffe met with Rodr\u00edguez Castro, Interior Minister L\u00e1zaro \u00c1lvarez Casas and the head of Cuban intelligence services, and discussed intelligence cooperation, economic stability and security issues. A CIA official confirmed the meetings to the AP.<\/span><\/p>\n<div>\n<div>\n<h3>May 15 <\/h3>\n<\/div>\n<\/div>\n<p><span>The Justice Department was preparing to seek an indictment against Castro, three people familiar with the matter told the AP.<\/span><\/p>\n<p><span>One of the people said the potential indictment was connected to Castro\u2019s alleged role in the 1996 shootdown of two planes operated by the Miami-based exile group Brothers to the Rescue. Castro was defense minister at the time.<\/span><\/p>\n<p><span>All three people spoke on the condition of anonymity because they weren\u2019t authorized to discuss an ongoing investigation. The Cuban government did not respond to a request for comment on the potential indictment, which was reported earlier by CBS.<\/span><\/p>\n<div>\n<div>\n<h3>May 18<\/h3>\n<\/div>\n<\/div>\n<p><span>The State Department imposed a new layer of sanctions on several Cuban government agencies, including the Interior Ministry and National Police and Intelligence Directorate, as the Trump administration continued to ratchet up pressure against the island.<\/span><\/p>\n<div>\n<div>\n<h3>May 20<\/h3>\n<\/div>\n<\/div>\n<p><span>Federal prosecutors announced a grand jury indictment against Castro in connection with the shootdown of the two Brothers to the Rescue planes in 1996.<\/span><\/p>\n<p>Read more <a href=\"https:\/\/bostonrelocationinsider.com\/?p=803\">Officers who defended Capitol from rioters sue to block payouts from $1.8 billion \u2018anti-weaponization\u2019 fund<\/a><\/p>\n<\/div>\n<\/article>\n","protected":false},"excerpt":{"rendered":"<p>President Trump has been escalating talk on regime change in Cuba after the military action in Venezuela early this year resulted in the capture of President Nicol\u00e1s Maduro.<\/p>\n","protected":false},"author":1,"featured_media":808,"comment_status":"open","ping_status":"closed","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[2],"tags":[],"class_list":["post-809","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-politics"],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v27.6 - 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