Trump with Cuba: Good Cop or Bad Cop?

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HAVANA TIMES – “Good cop, bad cop” is a negotiation tactic that resembles the interrogation of a prisoner by two officers. One agent shouts and threatens, while the other corrects his colleague and speaks kindly to the suspect, proposing that he cooperate. Both cops (or representatives of a powerful company or international power in talks with someone less empowered) act in coordination. In fact, a single negotiator can play both roles at different moments in the dialogue. The contrast between friendly treatment and violent threats is supposed to persuade the other side to give in.

President Trump, who on January 29 declared Cuba an “extraordinary threat” to the United States while promoting drastic coercive measures against our economy, is presenting himself to the Cuban establishment with the faces of both “cops” at once—although for many international analysts these are really just two faces of a gangster. Trump, founder of the Board of Peace (a supposed body to resolve international conflicts as a substitute for the UN), capped the first two months of 2026 by eliminating top leadership figures in two countries declared “hostile.”

Politicians, analysts, and ordinary commentators around the world, including in Cuba, have been divided in assessing these achievements of the US administration. Some consider them blatant violations of international law, perhaps even crimes against humanity, while others see them as commendable feats to free two peoples from cruel dictatorships. There are always those who say it is worth bending international law a little in order to make room for human rights.

In Venezuela, Trump managed with minimal losses to “extract” President Maduro to the United States and take control of the country’s oil under advantageous agreements, leaving the institutional structure intact in the hands of an accommodating acting president: Delcy Rodriguez. Cuba lost the already diminished supply of that oil, along with dozens of combatants—apparently defending Maduro’s security—and contracts for medical services and other arrangements. Chavismo was left moribund; its more radical spokespeople—such as Diosdado Cabello—have fallen silent, and in almost official terms there is talk of a betrayal in which Cuba ended up being instrumentalized.

But it was also a signal to other countries, and many in the opposition—and perhaps some within the Cuban establishment—would like to see something like that happen here. An almost instantaneous action that suppressed an international conflict at relatively low cost. Why not? some Cuban bureaucrat or comfortable capitalist might say. However, there are still no signs of a “democratic transition” in Venezuela.

Before the operation, Maduro received two invitations from the president of Belarus, Alexander Lukashenko (the first through anonymous sources, the second publicly before the press), to “self-extract” to his country. It seems this was a “friendly” message from Trump, transmitted through Putin, to let him know that his days as a leader were numbered. Maduro did not listen, but once in the United States he returned the “friendly” gesture to his captors by wishing them a “Happy New Year.”

In Iran, things were different. Missiles from Israel and the United States eliminated the Supreme Leader, his family, and his associates, to the point that Trump acknowledged that the aspiring Persian “Delcy Rodríguez” had also been physically eliminated. Iran continues to be the target of air strikes against military and police facilities, with the corresponding “collateral damage.” The region sinks into the hell of a war without end.

Thus, Venezuela would be for the Cuban establishment a message from Trump in his “good cop” mode (leaving open the question of which Cuban leaders might be “extracted,” or disappear under the rug), while Iran would show his “bad cop” side.

As always in Cuba, opinions are divided. One part of Cuban activism firmly denounces Trump and his Zionist allies/patrons as “global gangsters,” while another places its hopes for what it calls “liberation” in a US intervention. On social media, humorous memes circulate “accusing” Iran of “cutting in line” (a Cuban expression used when someone violates the natural order of a line or queue: the joke being that Cuba should have received its “liberation” before Iran).

Are Cuba–USA Talks Underway?

Meanwhile, reports continue to appear in more reputable press outlets about ongoing negotiations between senior representatives of the Cuban establishment—whose chief delegate would reportedly be Juan Guillermo Rodriguez Castro, 41, the grandson and personal security chief of Raul Castro, and son of the late General Luis Lopez-Calleja, who led the military holding company GAESA, which is said to control 60% of the Cuban economy—and counterparts from Marco Rubio’s team. The meetings are said to have taken place in Mexico and San Cristobal (on the sidelines of CARICOM’s annual summit).

Although the Cuban government publicly dismissed the existence of such talks, it has not issued any categorical denial, even after Mike Hammer, the US chargé d’affaires in Havana, stated that a process is underway through which Cuba would make a number of sensitive concessions to Trump. In another context, such statements—at the very least questionable—might earn someone the status of persona non grata. But Cuba, on the one hand, is under extreme pressure from economic sanctions that have pushed it to the brink, and on the other, Cuban leaders have always been very cautious about expelling US diplomatic personnel, in order to avoid a virtual total collapse of bilateral relations that could provoke uncontrollable scenarios.

Under these circumstances, hours before the Israeli and US attack on Iran (which in turn occurred almost immediately after the foreign minister of Oman—the mediator—told the press that an agreement between the two sides was ready on the main disputed issues: Cuba, take note!), Trump astonished the world by proclaiming that the United States would carry out a “friendly takeover” of Cuba.

The meaning of those words immediately became fodder for social media, since as often happens with Trump’s phrases, it is not clear what exactly he intends to communicate.

It sounds like the “good cop.” It creates expectations. But it reduces clarity in the complex matter of Cuba–US relations, in which since the beginning of the last century the issue of sovereignty has been key in Cuba—precisely the issue that such a phrase seems to cancel.

And Cuban Politicians?

Even the opposition most hopeful about a possible “liberation” from the North has expressed doubts. Cuba’s Foreign Ministry made no statement, and the president published a tweet with his usual slogans without mentioning Trump. Only the MAGA/annexationist segment of the Cuban opposition seems comfortable with the suggestion, although they point out the possibility of a “fraudulent change” if the “cop” Trump turns out to be too “friendly” with the Cuban establishment. Once again, social media filled up with memes, many of them sexualized. Some internet users even suggested that the Trump corporation was negotiating a purchase of GAESA assets.

After the events in Caracas, Marco Rubio had already said he would like to “see regime change in Cuba, but that does not mean we (the United States) would carry out that change.” The Trump administration expresses a preference for guarantees of hemispheric dominance, breaking the Cuban establishment’s geopolitical alliances with China and Russia, and ensuring open doors for US capital, with proper guarantees in the form of internal economic reforms of a privatizing nature. “Good cop”?

In a sort of executive ping-pong between “good cop” and “prisoner,” the Cuban government authorized the importation of fuels by private economic actors. Immediately afterward, Marco Rubio allowed US companies to sell fuel to private counterparts in Cuba. Days later, Rubio declared that he had done nothing new—that this had already been allowed before—and that the decisive step had been taken by Cuba. Then, suddenly turning into the “bad cop,” he later capped it off by prohibiting Cuban banks from being used for such transactions.

The oil that now arrives in ISO tanks the size of shipping containers has an additional advantage for Cuba: it can be received in ports such as that of the Mariel Special Economic Zone, while the large oil terminal in Matanzas still cannot fully unload tankers due to the destruction of its facilities in the catastrophic fire of 2022.

The Cuban government has been announcing several important reforms: opening private nursing homes and caregiving agencies (equivalent to the privatization of a segment of the health sector); greater autonomy for businesses and municipalities (the municipality is called upon to be a main actor in economic relations with the population, though in practice its current possibilities for doing so are minimal); and authorization for partnerships between state companies and private entities (practically the privatization of the most profitable functions within the state structure). Will the “good cop” respond to these steps?

From Hugo Cancio, the “most influential and controversial” Cuban-American businessman and owner of Katapulk—a powerful commercial agency operating between both countries—to the president and prime minister of Cuba, public statements in recent days have acknowledged the need for “urgent changes” in the island’s economy, while Trump’s team talks about the removal of Díaz-Canel.

The young Cuban political scientist Iramis Rosique recently published an interview in the international leftist outlet El Salto in which he defends economic reforms for Cuba without political changes. A graduate in Foreign Service from ISRI (Cuba’s prestigious diplomatic academy), Rosique could function as a spokesman for the reformist and politically correct sector of the establishment. But in Cuba, paying any attention to Trump—even in his “good cop” version (“economic reforms” without “regime change under pressure,” something similar to what Rosique proposes, and what the more radical opposition would call a “fraudulent change”)—is not only an ideological problem but also a legal one.

Article 224 of the Cuban Constitution declares irrevocable the “prohibition on negotiating under aggression, threat, or coercion by a foreign power.” Since the Cuban government itself has acknowledged the existence of aggression and coercion by the United States, it is understandable that its spokespeople maintain a certain antiseptic distance in not admitting that conversations with the Trump administration are taking place, while avoiding to appear to violate the Constitution. However, the real reasons may be diplomatic discretion and the creation of smokescreens to conceal the true terms of possible agreements.

Meanwhile, Cuban some opposition groups have launched a so-called “Liberation Agreement” for the transition in Cuba, though its terms remain equally undisclosed.

Read more from Cuba here on Havana Times.

One thought on “Trump with Cuba: Good Cop or Bad Cop?”

Raul Rufin March 7, 2026 at 10:36 amPermalink While I can understand the animosity that some might have towards communism here in the the USA I also cannot understand the animosity. I was born in the USA to Cuban parents. Living in Miami I grew up around Cubans mostly. Yet I was one of the few that would visit Cuba. I experienced the people; the island. They are different from those in Miami. The real Cubans – those in Miami – make me proud to be Cuban. The art. The innovation. The energy. Yet those around me only knew what they left behind or were told. I haven’t been back in 10+ years (because of Trump). Cuba has beaten, jailed, and silenced citizens critical of the government. Yet so has the USA. Cuba is 60 years into the revolution. 60 years into the American revolution: we had no president for the first 10-20 years, slavery, and we silenced anyone critical of the government with the Alien + Sedition Act. In the 60s the USA jailed people that were even kind of open to socialism or communism, or were merely accuse of it. Beyond that we continue to oppress the press – see: US late night hosts and Don Lemon to name a couple. I wore a watermelon pin to show my support for Palestine and my job asked me to keep it out of guest sight. So why does everyone blame Cuba’s communist regime for such acts when those are common across all governments, especially in the first 60 years after a revolution? If you think you aren’t safe to criticize the government in Cuba, just know that in the USA they’re creating militias – ICE – similar to the gestapo (beating up, killing, and arresting people) while amassing databases with facial recognition to oppress and target non-whites or those critical of the actions of the administration. Maybe it’s the poverty and homelessness I see all around me in the USA, but I don’t hate communism the way that US propaganda intended me to. Instead I wonder how much better the world would be if these 2 contrasting ideas learned to build each other up or coexist rather than make it their mission to destroy each other. The people of Cuba are the ones that suffer because of the games between the US and Cuba. I love you Cuba. Hopefully I can see you soon. Thank you for these articles. I am happy to see someone who is being honestly critical of Cuba while still wanting Cuba’s people to be successful.

While I can understand the animosity that some might have towards communism here in the the USA I also cannot understand the animosity.

I was born in the USA to Cuban parents. Living in Miami I grew up around Cubans mostly. Yet I was one of the few that would visit Cuba. I experienced the people; the island. They are different from those in Miami. The real Cubans – those in Miami – make me proud to be Cuban. The art. The innovation. The energy. Yet those around me only knew what they left behind or were told. I haven’t been back in 10+ years (because of Trump).

Cuba has beaten, jailed, and silenced citizens critical of the government. Yet so has the USA.

Cuba is 60 years into the revolution. 60 years into the American revolution: we had no president for the first 10-20 years, slavery, and we silenced anyone critical of the government with the Alien + Sedition Act. In the 60s the USA jailed people that were even kind of open to socialism or communism, or were merely accuse of it. Beyond that we continue to oppress the press – see: US late night hosts and Don Lemon to name a couple. I wore a watermelon pin to show my support for Palestine and my job asked me to keep it out of guest sight.

So why does everyone blame Cuba’s communist regime for such acts when those are common across all governments, especially in the first 60 years after a revolution?

If you think you aren’t safe to criticize the government in Cuba, just know that in the USA they’re creating militias – ICE – similar to the gestapo (beating up, killing, and arresting people) while amassing databases with facial recognition to oppress and target non-whites or those critical of the actions of the administration.

Maybe it’s the poverty and homelessness I see all around me in the USA, but I don’t hate communism the way that US propaganda intended me to. Instead I wonder how much better the world would be if these 2 contrasting ideas learned to build each other up or coexist rather than make it their mission to destroy each other. The people of Cuba are the ones that suffer because of the games between the US and Cuba.

I love you Cuba. Hopefully I can see you soon.

Thank you for these articles. I am happy to see someone who is being honestly critical of Cuba while still wanting Cuba’s people to be successful.

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