According to a report in The Wall Street Journal, the Trump administration is hoping to “cut a deal” to facilitate the end of communist rule on the island nation. “Emboldened by the U.S. ouster of a Venezuelan strongman, the Trump administration is seeking Cuban government insiders who can help cut a deal to push out the Communist regime by year’s end,” the outlet writes. Exclusive: Emboldened by the U.S. ouster of a Venezuelan strongman, the Trump administration is seeking Cuban government insiders who can help cut a deal to push out the Communist regime by year's end. https://t.co/yz7UwKKUbb — The Wall Street Journal (@WSJ) January 22, 2026 More from the New York Post: A “concrete plan” for doing away with the communist government that has ruled Cuba for nearly 70 years has not yet been developed, according to the outlet, but the government’s grip on the island has never been more fragile. In the wake of Venezuelan dictator Nicolas Maduro’s ouster, Cuba’s economy is on the brink of collapse, US officials told the outlet. US intelligence assessments indicate the island is facing chronic shortages of basic goods and medicines and is suffering from frequent blackouts. Cuba depended on Maduro for oil, and the island could run out of fuel within weeks. The Trump administration aims to prevent any more Venezuelan oil from flowing to Cuba to weaken the regime further. Maduro’s capture by US forces and the subsequent success the Trump administration has had in getting concessions from the Venezuelan government is being viewed as a blueprint for Cuba, US officials said. Daily Mail noted the U.S. strategy of identifying members of the Cuban government who are sympathetic to American interests is a similar plan used to capture Maduro in Venezuela. Someone in Maduro’s inner circle turned on him, aiding his capture in Caracas, the capital of Venezuela. “THERE WILL BE NO MORE OIL OR MONEY GOING TO CUBA,” Trump said earlier this month. “I strongly suggest they make a deal, BEFORE IT IS TOO LATE,” he added. “…THERE WILL BE NO MORE OIL OR MONEY GOING TO CUBA – ZERO! I strongly suggest they make a deal, BEFORE IT IS TOO LATE. Thank you for your attention to this matter.”- President Donald J. Trump pic.twitter.com/bHEIysJ7q1 — The White House (@WhiteHouse) January 11, 2026 Daily Mail explained further: Some US officials and Trump allies, some of them Florida-based Cuban exiles, want an aggressive approach to end the nearly 70 years of Communist rule. Others within the administration have pointed out prior disastrous attempts to overthrow or weaken the Castro government, including the failed Bay of Pigs invasion and the trade embargo. The embargo was instituted in 1962 and Cuba’s leaders have remained in place. These same officials have also argued that Venezuela is much different from Cuba, even though they both have far-left governments. Cuba is a single-party state that does not allow political opposition and has violently suppressed the only two major protests in the decades since the Communists took over: one in 1994 in Havana and another in 2021 across the entire island. Meanwhile, Venezuela has had an active anti-Maduro faction for years. There have also been protests and elections, though international monitors virtually all agree that Maduro was able to rig the contests so he’d win no matter what. Because Venezuela has the makings of an opposition movement, some Trump officials say replicating what was done there could be difficult in Cuba, where citizens are extraordinarily repressed. Given how dicey a regime change operation could be in Cuba – with the potential to lead to a humanitarian crisis – Trump believes that ending the long reign of the Castros would cement his foreign policy legacy, according to a US official who worked for Trump on Cuba policy in his first term. It would give Trump a leg up on President John F. Kennedy, who did not succeed in rooting out Fidel Castro. The Trump administration is getting more open about its desire to see a conclusion to the regime in Cuba.