Donald Trump attempted to overthrow the governments of both Cuba and Venezuela during his first term. This time round, the goal remains the same, though some of the methods have changed.
Also in this week's newsletter:
Presidents of Mexico and Colombia to snub Summit of the Americas
Cuba "categorically rejects" involvement in Russia-Ukraine war
Trump deports more Cubans to Eswatini
High-profile Cuban dissident leaves Cuba for U.S.
Trump’s Big Bold Regime Change Plans
As the Trump administration escalates its campaign of threats and military posturing toward Venezuela, Cuba is calculating the potential costs – from more sanctions and fuel shortages to the possibility that its closest ally could even be invaded.
In recent months, Trump has ramped up troop numbers in the region to 10,000 and killed 21 people in strikes targeting several small boats. The administration claims the vessels were transporting drugs from Venezuela, although no evidence has been provided that they were in fact carrying narcotics. Meanwhile, the State Department has doubled a bounty on Venezuela's President Nicolás Maduro to $50 million. The Trump administration has called him “one of the largest narco-traffickers in the world" and accused him of running a drug cartel, a claim disputed by Mexico's president, among others.
Today, the New York Timesreports that the Trump administration has authorized the CIA to conduct covert "lethal operations" in Venezuela and the Caribbean that could be unilateral or "in conjunction with a larger military operation."
All this has come on top of economic warfare on Venezuela – among other regime change efforts – that have been ongoing since Trump's first term.
This “maximum pressure” strategy also encompassed regime change efforts aimed at Cuba. The two countries, along with Nicaragua, were labeled “the Troika of Tyranny” by John Bolton in 2018 when he was Trump’s national security advisor. More recently, Secretary of State Marco Rubio referred to them as "enemies of humanity.”
During Trump’s first term, his administration blamed Cuba for “propping up” Venezuelan President Nicolás Maduro. Bolton accused Cuba of sending 20,000 to 25,000 security officials to Venezuela, a baseless claim that was used to justify efforts to overthrow the Cuban government.
There were indeed 20,000 Cubans in Venezuela. Most were doctors and nurses providing free healthcare. In exchange, Venezuela exported oil to Cuba at a discount.
The first Trump administration targeted this economic lifeline, imposing sanctions that cut the flow of oil from Venezuela to Cuba. Trump officials went so far as to push the CIA to covertly sabotage oil tankers — the CIA balked at the plan. Watch Episode 2 of our award-winning documentary series The War on Cuba, in which we document the impact of these sanctions and take a close look at Cuba-Venezuela relations.
Ultimately, the “maximum pressure” strategy failed to bring about regime change in either Cuba or Venezuela. Some analysts speculated that in a second term, Trump, whose MAGA base was at odds with neoconservatives like Bolton, would try a different approach.
In the early months of the administration, Trump envoy Richard Grenell met with Maduro, negotiating the release of six U.S. detainees. Grenell's diplomacy appeared to contradict the hard-line game plan favored by Rubio, the self-proclaimed architect of Cuba policy during Trump’s first term.
But since then, Rubio seems to have won the battle for Trump’s ear as he and other top administration officials push for Maduro's ouster. On October 2, the U.S. broke diplomatic ties with Venezuela.
Meanwhile, Rubio has overseen a ratcheting up of the U.S. government’s economic war on Cuba, which aims at stripping the country of its sources of foreign currency and isolating it from the rest of the world.
For now, though, the focus of Trump’s regime change efforts seems to be Venezuela.
A change in government in Venezuela would be a big blow for Cuba, which continues to rely on its main ally's political support and oil (although shipments have significantly declined in recent years).
To better understand Marco Rubio’s role in dictating U.S. regime change efforts aimed at Venezuela and Cuba, read the latest article by Lee Schlenker for Responsible Statecraft.
Also, watch (in an interview with Zeteo’s Mehdi Hasan) Cuba’s Deputy Foreign Minister Carlos Fernández de Cossío explain how U.S. sanctions on Cuba and Venezuela have made it more difficult for Cuba to import vital fuel and spare parts.
Presidents of Mexico and Colombia To Boycott Summit
Mexico’s president Claudia Sheinbaum announced Monday that she would not attend the Summit of the Americas this December after the Dominican Republic, the event's host, announced that Cuba, Venezuela and Nicaragua would not be invited.
“We do not agree with the exclusion of any country,” Sheinbaum said (watch a video of her statement).
On Wednesday, Colombia's president Gustavo Petro followed suit: “I will not attend the Summit of the Americas. Dialogue does not begin with exclusions."
According to Cuba’s Ministry of Foreign Affairs, the D.R.'s move to exclude the three countries is a result of “brutal and unilateral pressure” from Secretary of State Marco Rubio.
The Summit of the Americas has been held every three years since 1994 by the Organization of American States (OAS). Cuba was expelled from the OAS in 1962, while Venezuela and Nicaragua withdrew in 2019 and 2021, respectively. All three have participated in the summit in the past.
Sheinbaum also attributed her decision to the recent floods in Mexico, which have so far killed over 60 people, while Petro referenced U.S. military escalation in the Caribbean as another reason for his refusal to participate.
Sheinbaum’s predecessor, Andrés Manuel López Obrador, boycotted the 2022 Summit in Los Angeles after the Biden administration refused to invite the three countries. Several other heads of state also refused to participate. Watch our video about the 2022 summit boycott.
Cuba "Categorically Rejects" Involvement in Ukraine
Cuba’s Ministry of Foreign Affairs (MINREX) has released a statement that "categorically rejects" it is involved in the war between Russia and Ukraine, describing accusations that Cuba is sending troops to support Russia as "slanderous." Reuters has reported that the U.S. State Department is directing its diplomats to lobby against Cuba’s upcoming resolution at the UN condemning the U.S. embargo on Cuba by claiming the island is supporting Russia in the Ukraine war, with allegedly 5,000 troopsfighting on the ground. The figure seems to stem from Ukrainian intelligence services.
Cuban-American hardliners had already seized on the allegations of "Cuban regime troops" fighting in Ukraine, organizing a national security briefing in Congress last month that featured members of Ukraine's government and intelligence services.
Ukraine is, needless to say, a major U.S. ally whose intelligence services work closely with U.S. intelligence agencies. The charges that Cuba is sending troops to Ukraine mirror those made several years earlier that Cuba was sending troops to Venezuela (see above). Both serve the purpose of isolating Cuba and justifying the U.S. government's policy of economic warfare on the island.
There are Cubans fighting in the Ukraine war, although their actual numbers have not been independently verified. Some of these Cubans say they were manipulated into joining the war through promises of Russian passports.
But no credible evidence has surfaced that the Cuban government is encouraging or facilitating its citizens to join the Russian military.
According to MINREX, the Cuban government "maintains a zero-tolerance policy" toward mercenary activities in other countries, and has taken steps to "neutralize recruitment" in Cuba. Since 2023, Cuban courts have found 26 people guilty of mercenarism in Ukraine, with sentences ranging from five to 14 years in prison.
Don't Miss Deadline to Register for Our Trips to Cuba!
For years, we’ve told Cuba’s untold stories. Now, we’re inviting you to experience them firsthand.
In this video, Belly of the Beast journalist Liz Oliva Fernández shares what makes this journey special — and how your participation supports independent journalism.
Don't miss the deadlines for our two upcoming trips to Cuba:
November 1–8 (Deadline: October 20) December 6–13 (Deadline: November 15)
Trump deports more Cubans to Eswatini. A group of ten men – including an unknown number of Cubans – has been deported from the U.S. to Eswatini (formerly Swaziland) in southern Africa, Axios reports. It's the second group of migrants to be deported from the U.S. to Eswatini since Trump took office. The first was made up of five men – including one Cuban – who landed there in July. Since assuming office, Trump has deported numerous immigrants to third countries with which they have no connection. In addition to those deported to Eswatini, two Cubans were deported to South Sudan earlier this year.
Prominent Cuban dissident leaves Cuba for U.S. One of the most renownedCuban dissidents, José Daniel Ferrer, left the island for the United States on Monday, the Cuban government said in a statement (in Spanish). Ferrer’s departure and that of his family is the result of a “formal request” of the U.S. government, which he accepted, according to the statement. U.S. officials have long publicly championed Ferrer. “We are glad that Ferrer is now free from the regime’s oppression,” Marco Rubio said in a statement. Ferrer's exile to the U.S. occurs as the Trump administration continues to deport Cubans who lack his political connections. Watch our video about one of them, Heidy Sánchez, who was separated from her infant daughter.
José Daniel Ferrer and U.S. Chargé d'Affaires Mike Hammer in Santiago de Cuba, February 2025
Liz Oliva Fernández reports from Santiago de Cuba in the wake of Hurricane Melissa. Also: Our doc Health Under Sanction is now online! U.S. offers aid to Cuba but obstructs relief efforts Analysis: Why 7 countries voted against Cuba's UN resolution Cuba's former ally Ukraine downgrades diplomatic relations Former Cuban minister charged with espionage Melissa Batters Cuba: Our Report on the Ground Belly of the Beast journalist Liz Oliva Fernández was in Guamá, the municipality in the province...
Our latest documentary Health under Sanction has just dropped! With exclusive access to Cuba's dilapidating hospitals, we follow the patients on the sharp end of the U.S. government’s economic war on Cuba — and the doctors fighting to keep them alive. The 25-minute film is directed by Ed Augustin and Reed Lindsay and produced by Belly of the Beast for People & Power, Al Jazeera’s award-winning investigative documentary program. Watch it now! Until recently, Cuba’s healthcare system was a...
Washington has spent weeks trying to strong-arm the world into voting against Cuba’s annual resolution at the UN opposing the U.S. embargo. It didn’t work. See more details about the vote below. Meanwhile, as Hurricane Melissa tore through the island, Belly of the Beast journalist Liz Oliva Fernández has been on the ground in Santiago de Cuba reporting on the storm’s impact and the resilience of those in its path. In other news: Red state farmers want to trade with Cuba Cuban deported from...
