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U.S. companies were driven out of Venezuela due in part to sanctions enacted by Donald Trump during his first term.
The same dynamic played out in Cuba, where Trump imposed “maximum pressure” measures that effectively expelled U.S. companies, destroyed the island's economy and fueled unprvecedented migration to the United States.
Now, Trump says the U.S. will take control of Venezuela’s oil industry and is warning Cuba to “make a deal…BEFORE IT IS TOO LATE.”
This week, we look at what this deal might look like and how Trump’s foreign policy in his first term created the crises in Venezuela and Cuba that he now claims to be trying to solve.
Also:
- Marco Rubio: President of Cuba?
- No plans for invasion against “tough Cubans”
- Cuba ramps up combat training
- Venezuela and Cuba reaffirm solidarity
- Cuba is not yet receiving more Mexican oil
- U.S. Ambassador to Cuba...or Miami?
- U.S. sends hurricane aid to Cuba — two months later
Creating the Crisis, Claiming the Cure
Donald Trump invented a drug cartel to justify abducting Venezuela’s president so U.S. oil companies could get back into the country. The irony is that his own sanctions were a reason they were forced out in the first place.
“We left under the sanctions in 2019,” Halliburton CEO Jeff Miller told Trump at a gathering of oil executives at the White House on Friday. “We had intended to stay, and then when the sanctions went into place, we were required to leave.”
Trump began imposing new sanctions on Venezuela in 2017 and strengthened them in 2019, leading to a decline in average caloric consumption among Venezuelans, rising rates of illness and death, and the displacement of millions due to deteriorating economic conditions, according to a study by the Center for Economic and Policy Research.
Cuba was being squeezed at the same time. Sanctions drove out U.S. companies, destroyed the economy, impoverished the population and pushed more than a million Cubans to migrate to the United States. Now, Trump is claiming Cuba is on the verge of collapse, but his own policies have created the very crisis that is being used to justify Washington’s calls for regime change.
"I have a future here"... then Trump won
Despite the history of acrimony between the two countries, Cuba has long shown a desire to normalize relations. Just over a decade ago, in December 2014, the two countries began doing just that after Barack Obama and Raúl Castro brokered a historic detente. The countries “re-established diplomatic relations,” and Obama became the first sitting U.S. president to visit Cuba since 1928.
The deal brought in both U.S. companies and visitors to the island, boosting the economy and giving many Cubans hope for a better future.
"I hardly had time to rest," Havana taxi driver Oscar Álvarez told Belly of the Beast. "We picked up passengers at the cruise ship terminal, and we didn’t stop all day."
“Havana was overcrowded: celebrities, musicians, politicians — everybody. Chanel runway, Fast and Furious shooting, Rolling Stones concert,” Cuban fashion designer Idania del Río told journalist Liz Oliva Fernández in our documentary series The War on Cuba. “The mood was ‘anything is possible,’ all this sense of change, and finally to be aware of: ‘I have a future here. I can stay here. I don’t have to leave my country.’ But then Trump won the election.”
Since 2017, Cuba has been subject to a barrage of “maximum pressure” sanctions imposed by Trump and largely kept in place by Joe Biden. Some of the measures, like the 2019 U.S. ban on cruise ship visits, battered Cuba’s economy and the fledgling private sector.
"You could really see the difference when the American cruise ships stopped," said Álvarez. "They left a big hole, and not just for us. They gave life to the whole city."
Now, after forcing U.S. companies out of Cuba just like he did with Venezuela — and blocking all shipments of Venezuelan oil to the island — Trump has warned that Cuba is about to collapse and better make a deal “BEFORE IT IS TOO LATE.”
“We’re talking to Cuba, and you’ll find out pretty soon,” he told reporters Sunday on Air Force One. Cuba on Monday denied any negotiations were underway.
What would a Trump deal with Cuba look like?
It’s not clear whether Trump’s endgame in Cuba is wholesale political change, which has long been Washington’s take-it-or-leave-it approach, or striking a deal that opens the island to U.S. companies while leaving the political system intact, as he did with Venezuela’s acting president, Delcy Rodríguez.
Marco Rubio and his fellow hardliners have not been subtle about their aspirations for Cuba. Rep. Carlos Giménez (R-FL) last week posted a map on X, showing U.S. company logos scattered across the island with the accompanying text: “POV: Cuba soon.” He wrote: “When the inevitable happens in #Cuba & the narcoterrorist dictatorship is no more, there won’t be a company that won’t want to invest in the stunning, beautiful island of my birth."
Fact check: Far from a “narcoterrorist dictatorship,” Cuba is arguably the U.S. government’s most reliable security partner in the Caribbean. See Liz Oliva Fernández’s report on Cuba’s counternarcotics efforts.
While Cuban-American hardliners have long salivated at the prospect of the U.S. recolonizing Cuba, Trump in the past seemed interested in investing in the island without regime change. In 2008, Trump’s brand name was registered with Cuba’s Office of Industrial Property for hotels, casinos, beauty contests, television programs and golf courses. And Trump Organization executives have visited Cuba on different occasions, smoking cigars, playing golf and scoping out business opportunities.
“Trump does not have a principled opposition to Cuban socialism,” said William LeoGrande, professor of government at American University. “He was willing to go and work with the socialist government of Cuba to build a hotel and a casino.”
Trump endorsed Obama’s detente in March 2016. “After 50 years, it’s enough time, folks,” he said at a Republican primary debate in which he faced off against Rubio, then a senator.
But after winning the presidential primary, Trump cut a deal with Rubio, getting his support both in Florida and in the Senate in exchange for endorsing Rubio’s hard-line policy toward Cuba.
Trump, who once called Rubio a “lightweight choker” and “corrupt politician,” now seems intent on making him and his Cuban-American allies happy.
When a reporter asked Trump on Sunday what kind of deal he was looking for with Cuba, he responded: “One of the groups I want taken care of are the people that came from Cuba that were forced out or left under duress.”
Marco Rubio: President of Cuba?
Trump on Sunday re-posted a joke about Rubio becoming Cuba’s president, replying: “Sounds good to me!”
In Rubio’s 2012 memoir, An American Son, he wrote that as a child: “I boasted I would someday lead an army of exiles to overthrow Fidel Castro and become president of a free Cuba.”
Rubio was exposed years ago for falsely claiming that his family fled Cuba because of communism. He has never stepped foot in Cuba, and his parents immigrated to the United States when Washington-backed dictator Fulgencio Batista was running the country.
No apparent plans for invasion against “tough Cubans”
During an appearance on right-wing commentator Hugh Hewitt’s talk show on January 8, Trump suggested a Cuba intervention isn’t likely.
“Is it time to increase the pressure [on Cuba], maybe even quarantine it as you have Venezuela?” asked Hewitt. “Well I don’t think you can have much more pressure other than going in and blasting the hell out of the place,” said Trump. “Cuba’s really in a lot of trouble. But people have been saying that for many years, in all fairness, about Cuba. Cuba’s been in trouble for the last 45 years, and they haven’t quite gone down. But I think they’re pretty close of their own volition.”
Cubans ramp up combat training
A “territorial defense day” took place on Sunday in various provinces across Cuba — Villa Clara, Camagüey, Artemisa and Pinar del Río — to hone Cuban armed forces’ and civilians’ combat skills. Trainings were held for shooting, throwing grenades, anti-aircraft defense and more. “Actions were carried out in response to situations of risks, threats and aggressions to the security of the interior of the territory in a scenario of unconventional warfare and the fight against invasion,” reported Canal Caribe.
Venezuela and Cuba reaffirm solidarity
Venezuela's Health Minister Magaly Gutiérrez met on Saturday with Cuban officials to reaffirm the two countries’ commitment to public healthcare and resistance to U.S. pressure.
The countries have been close allies since socialist leader Hugo Chávez was elected president of Venezuela in 1998. In 2000, the Comprehensive Agreement for Cuba-Venezuela Cooperation, signed by Fidel Castro and Chávez, created an alliance exchanging Venezuelan oil for Cuban social services, particularly in the field of healthcare. For more on this exchange, read our recent article and watch Episode Two of The War on Cuba.
Venezuela released an official statement on Sunday emphasizing that its relationship with Cuba is in accordance with the UN Charter and international law. The statement read: “International relations must be governed by the principles of international law, non-intervention, the sovereign equality of states and the self-determination of peoples.”
Venezuela hasn't said it's going to stop sending oil to Cuba, but the U.S. says it’s blocking all oil shipments out of the country. Meanwhile, it’s not clear what will happen with the estimated 10,000 Cuban health professionals who work in Venezuela.
Cuba is not yet receiving more Mexican oil
Mexico's President Claudia Sheinbaum said on January 7 that her country has not substantially increased the volume of oil it sends to Cuba.
Mexico surpassed Venezuela in 2025 to become Cuba’s leading source of oil, according to a Financial Times report.
Despite Trump’s announcement on social media that Venezuela would no longer be sending oil to Cuba, current U.S. policy allows Mexico to continue sending oil to the island, U.S. Energy Secretary Chris Wright and another official told CBS.
Rep. Carlos Gimenez threatened Sheinbaum on social media, alleging that “she claims to be a friend of the USA and then betrays us by providing free oil to the dictatorship in #Cuba. This must stop immediately. The consequences will be severe.”
U.S. Ambassador to Cuba...or Miami?
U.S. Chargé d’Affaires to Cuba Mike Hammer held a press conference Wednesday in Weston, Florida, a Miami-area suburb. While it's unusual for an ambassador representing the United States in another country to be making press appearances on U.S. soil, this is standard practice when it comes to Cuba.
Since Trump assumed office and Rubio became Hammer's boss, the top U.S. diplomat to Cuba has spent much of his time meeting with pro-embargo activists, visiting South Florida and posting influencer-style social media videos from the island. He has encouraged Cubans to reach out to him about their “perspectives” and “ideas" — while his government imposes collective punishment on the Cuban people through economic warfare.
In one video, Hammer visited the beach resort town of Varadero, where he jokingly commented on the number of Russian tourists, but failed to mention that U.S. regulations prohibit U.S. tourism in Cuba and punish European tourists for visiting the island by stripping them of their visa waiver privileges. See Belly of the Beast journalist Yohan Rodríguez's video about Hammer's provocative social media videos here.
At the Wednesday press conference, which was held to announce U.S. hurricane aid to Cuba (see below for more) Hammer urged those present "not to pay attention to the propaganda coming out of Havana." Instead, he said, they should listen to Donald Trump and Marco Rubio.
U.S. sends hurricane aid to Cuba — two months later
The Catholic Church will start delivering $3 million in U.S. government humanitarian aid to people affected by Hurricane Melissa — more than two months after the hurricane hit the island.
It’s not uncommon for non-governmental humanitarian donations to face red tape due to U.S. sanctions. See our video on this subject here.
But it's not clear why this U.S. government donation, promised back in November, was so delayed.
Cuba's Ministry of Foreign Affairs released a statement on Thursday that accused the U.S. government of "opportunistically exploiting what appears to be a humanitarian gesture for purposes of political manipulation."
The statement read: “At no point has there been official communication from the U.S. government to the Cuban government to confirm this shipment." It added that material assistance from the U.S. "represents a fraction of the effort of the Cuban people and government and of the aid received from various parts of the world, including U.S. [non-profit] organizations."
Around $74 million is needed to address the devastation from the hurricane, according to the UN, which released $4 million in emergency funding ahead of the storm and $7 million afterward. The UN estimated Hurricane Melissa affected more than 1.7 million people and damaged over 150,000 homes.
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