​Last week, the United States stepped up the pressure, adding sanctions on five Cuban entities and eight individuals who help Cuba secure weapons and maintain relationships with foreign militaries. And it emerged that Secretary of State Marco Rubio, who has his own personal history with the island, was modeling the approach on the successful raid on Venezuela, casting around for current or former Cuban officials who could take over as leader if the government collapses, or is made to collapse.

So what’s going on?

Carrie Filipetti is the executive director at The Vandenberg Coalition, a nonpartisan network of foreign policy scholars. Before that, she was the deputy assistant secretary for Cuba and Venezuela at the State Department in Trump’s first administration. Who better to answer our questions about how Team Trump sees Cuba today?

Secrets: Six months into a fuel blockade on Cuba, what does everyday life look like in Havana?

Filipetti: The suffering of the Cuban people has not been only for six months. Arbitrary detention, systematic repression, political imprisonment, religious persecution, torture, and chronic rationing have defined life in Cuba for decades and only continues. While there have been reports of thousands of prisoners released, only a handful of those are political prisoners. Around 1,200 political prisoners remain jailed, while deaths from poor medical care, malnutrition, and torture continue. The repression is so extreme that between 2022 and 2023, far before sanctions enforcement, well over 10% of the Cuban population fled the island.

Things have worsened for the Cuban people with the collapse of the regime’s patron, Venezuela, and increased enforcement of fuel restrictions. That said, the United States has let fuel in to ease hardship and pledged $100 million in aid. European Union nations, especially Spain, have provided billions in assistance over the years. As Secretary Rubio notes, while the Cuban people suffer, regime officials like Raul Castro have built fortunes via state-owned enterprises like GAESA.

Secrets: Has this translated into political protests?

Filipetti: July 2021 saw the largest protests in decades in Cuba, significant for both their size and demographics. Young artists and performers like Luis Manuel Otero inspired waves of young Cubans to demand freedom. And as the protests increased, so did the repression. Otero Alcantara was among thousands of people picked up by Cuban police and was only freed, and forced into exile, over five years later.

That increase in repression had a chilling effect, but protests do continue. Earlier this year, there were protests against Communist Party offices in Morón, and there have been cacerolazos, a form of protest involving banging pots and pans, across the country. But it is very hard to go into the streets when you know the torture and repression that awaits you.

Secrets: What is U.S. policy toward Cuba?

Filipetti: Since 1996, bipartisan U.S. policy has supported a democratic transition in Cuba. In recent years, Democrats have generally pursued that goal through negotiation, while Republicans have favored maximum pressure.

President Trump’s first administration focused on the regime’s main sources of income — remittances, tourism, and the Cuban doctors program — to force meaningful concessions while at the same time expanding support for private Cubans. In his second administration, Trump has expanded that pressure through the indictment of Raul Castro, secondary sanctions, and stricter enforcement. More recently, the president threatened that Cuba is “next,” signaling a willingness to further increase pressure on the regime. 

Secrets: What are the chances of regime change/U.S. military intervention?

Filipetti: It’s nearly impossible to predict what President Trump will do, so it’s more useful to consider what he is balancing. First, there is national security. The Cuban regime allows adversaries like China to spy on our southeastern coastline, which is filled with sensitive facilities like combatant command headquarters and military bases. Cuba is also a state sponsor of terror, providing training and support to foreign terrorist organizations like the [Sandinistas in Nicaragua], ELN [in Colombia and Venezuela], and FARC [in Colombia].

There is also, however, the domestic consideration. We are a few months before midterms, and the president is already dodging questions about the wisdom of his operation in Iran. Facing this skepticism and without a clear road map to victory in Cuba, I would be very surprised if he attempted a military operation in the immediate future.

The question really boils down to what resources we are willing to contribute. Venezuela offers a caution. While we did engage in a military operation in Venezuela that successfully removed Maduro, seven months later, we still have not yet invested the resources necessary to bring democracy to the country. That is in a nation that had both a long history of democracy and existing natural resources to aid in reconstruction. Cuba has neither. While a free Cuba is a national security interest for the United States, continuing the pressure/support strategy seems more viable than kinetic regime change.

Secrets: Is there a constituency that would welcome further U.S. pressure or a military intervention? And to what extent does U.S. pressure strengthen support for the government?

Filipetti: There is a strong Cuban American and Venezuelan American community, particularly in Florida, that understands the nature of the Cuban regime and seeks change. And while there remains a constituency within Trump’s base that is very skeptical of intervention, polling has shown Trump voters are often more hawkish than traditionally believed. But even among those Americans who want to see change, the vast majority are calling for pressure, not necessarily military force. As for the Cubans themselves, they’re not calling for sanctions relief — they’re calling for “libertad.” They understand that the threat to their future stems not from Washington, but from the regime itself.

Correction of the day

The New York Times had a fascinating story from purple Arizona last week, headlined: Arizona’s Democratic Governor Set to Pick a Republican Running Mate.

Had Gov. Katie Hobbs (D-AZ) hit upon a brilliant strategy for keeping her job in a state that is leaning redder? Yes. Um, sort of. As this subsequent correction shows …

An article on Thursday about Democratic Gov. Katie Hobbs of Arizona planning to tap a former Republican mayor to serve as her running mate in her re-election bid referred imprecisely to John Giles, who is said to be the running mate pick. Mr. Giles, a lifelong Republican who served as mayor of Mesa, Ariz., recently changed his party affiliation to no preferred party; he is not currently a registered Republican.

Lunchtime reading

What the Iran-Oman Hormuz deal means (it’s not good): Optimism about reaching a diplomatic solution to the Iran crisis is premature, John Bolton writes. Indeed. The only mystery with this conflict is why there has been any optimism at all since it started. Bolton’s answer, you may not be surprised to know, is regime change …

All hail the thoughtful conservative pundit who gives MAGA ideas a respectable face: Matt K. Lewis on New York Times columnist Ross Douthat and his new role at 60 Minutes.

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