US Threatens Cuba With Trump’s Venezuela Blueprint

0:00The thing about AI for business, it may not automatically fit the way your business works. At IBM, we've seen this firsthand. But by embedding AI across HR, IT, and procurement processes, we've reduced costs by millions, slash repetitive tasks, and freed thousands of hours for strategic work. Now we're helping companies get smarter by putting AI where it actually pays off, deep in the work that moves the business. Let's create smarter business, IBM. If you follow markets, you know the value of long-term thinking. You plan, you diversify, you prepare for volatility. But in life, even the best strategies can't prevent every bad day.

0:41A fire, a loss, a disruption that demands immediate attention. When that happens, what matters isn't just what you planned, it's who shows up. That's where Cincinnati Insurance comes in. For more than 75 years, they've helped individuals and businesses navigate life's toughest moments with care, expertise, and personal attention. Together with independent agents, Cincinnati Insurance focuses on relationships, not transactions. Their approach is grounded in experience, follow-through, and trust built over time. Bad days happen, and when they do, you deserve an insurance partner who understands risk, respects what you've built, and is ready to help you move forward.

1:21The Cincinnati Insurance Companies. Let them make your bad day better. Find an independent agent at c-i-n-f-i-n dot com. Dog grooming genius here. Most people see a busy dog salon, but I see operational excellence. Thanks to Genius from Global Payments. Scheduling, personalized. Checkouts, instant. Absolutely genius. From game day crowds to every groomer in this shop, Genius keeps everything flowing seamlessly. Schnauzer is styled. Flawless execution. Big league reliability for any business. That's genius.

2:03Bloomberg Audio Studios. Podcasts, radio, news. They've really lost control of Cuba. The president's been clear he has other options. I'm not going to elaborate on what those are, but everybody knows what those are. The Trump administration is ratcheting up pressure on Cuba. We are announcing an indictment charging Raul Castro. On May 20th, which is Cuban Independence Day, the Justice Department indicted Cuba's former president, Raul Castro, in connection with the 1996 downing of two civilian planes. The U.S. military announced an aircraft carrier is in the Caribbean. Secretary of State Marco Rubio shared a video message online offering everyday Cubans the prospect of a relationship with the U.S.

2:49and blaming Cuba's troubles on the island's ruling elite.

2:58Rubio said,

3:02But nothing has been used to help the people. The Trump administration's latest pressure campaign comes five months into its near-total oil embargo of Cuba, which started when the U.S. took down Nicolas Maduro, the leader of Venezuela, Cuba's main international patron, and its biggest source of oil. And this is not just fuel for automobiles. That's Eric Martin, who covers the State Department and foreign policy for Bloomberg. This is oil that goes into electricity. They don't have the fuel that they need for food production, processed foods. They've had hospitals, schools that have urgent need for electricity that can't get it.

3:47Blackouts across the country have sparked protests. Cubans banging on pots and pans shouting, turn the lights on. And so you're hearing stories of people unable to be kept alive on ventilators, unable to get the kind of life-sustaining care that they need in hospitals because of these blackouts and this electricity shortage. All these latest turns, the indictment, the forceful rhetoric, and an unprecedented visit to the island by CIA Director John Ratcliffe earlier this month, Eric says that's widely seen as a signal the U.S. is ready to use military force. We've seen reports of an increase in intelligence gathering flights around the island.

4:28We've also seen even publicly President Trump talking about the U.S. military carriers like the Lincoln could stop off in Cuba on their way back from Iran. Eric says that Ratcliffe, during his visit, made it clear that the Cuban government needs to make fundamental changes to take President Trump seriously. Ratcliffe talking about U.S. willingness to partner with the Cuban regime on economic and political changes to help the Cuban people. But if you're not willing to accept our help and you think that the alternative is maintaining the status quo, look what we did in Venezuela at the beginning of the year.

5:10After months of buildup at 2.01 a.m. local time today in Caracas, Venezuela, U.S. Delta Forces slipped into the home of dictator Nicolas Maduro. There's two schools of thought among analysts here, one of which is that the Iran war is a cautionary tale that might make the administration reticent to get involved physically in Cuba in terms of any kind of military activity. But another is that as a political point that the administration may be looking to be able to put another win on the board like was broadly perceived with Venezuela, which was a two and a half hour operation to remove Maduro and that that could actually increase the risk appetite to do something in Cuba.

6:03I'm David Gurra, and this is The Big Take from Bloomberg News. Today on the show, the Trump administration's escalating threats against Cuba and how the U.S.'s attempt at regime change in Venezuela is playing out in that South American country.

6:21Eric, the U.S. has had an embargo in place on Cuba for more than six decades. Why is the U.S. amping up the pressure so much right now? This has been a goal of the Trump administration articulated in the national security strategy in December to counteract foreign malign actors in the Western Hemisphere. They principally have identified China, Russia, and to some extent Iran as well. These reports of Chinese presence in Cuba being one thing that the administration has identified indefinitely, pervasively in Venezuela. We saw a lot of Iranian actors in Venezuela. We saw a great number of Cuban intelligence agents living in Venezuela in recent years.

7:07For a long time, the understood arrangement was Venezuela would send this subsidized oil to Cuba to keep the lights on, to keep the economy going. And Cuba sent Venezuela doctors, but also in particular spies and intelligence agents. It seems like that moment in early January when the U.S. went in and removed Nicolas Maduro was something that was closely watched by the Cubans. Absolutely. That was the pivot point. You had this pressure building for years, really, since the COVID-19 pandemic. January 3rd was a pivot point for Cuba because Venezuela has filled this role that Cuba has needed for decades of a patron state.

7:47that previously it was the USSR until the fall of the Soviet Union. And now they're facing a similar challenge because the U.S., President Trump in January threatened with tariffs, secondary tariffs, any country that was supplying oil to Cuba. But the private sector has been able to buy from American and foreign companies. And that's been a big push from the administration is the theory that if you open the private sector and you get the private sector to grow, that that will result in both an economic but also political opening. How has the U.S. been ratcheting up pressure on Cuban officials?

8:24It's really the Castro family that still controls Cuba. 67 years after Fidel and Raul led their revolution to topple Batista, who had been supported by the U.S. in 1959, the understanding is that the Castro family, this company that they set up called Galesa, which is a military conglomerate and really runs the economy on the island is the real power broker on the island. So what we've seen with some of these steps, including the indictment of Raul Castro, is setting out a legal case, as we saw with Maduro. So what is the action that follows from that and drawing, connecting the dots to a potential military intervention of some kind, as we've seen lots of reporting from lots of outlets in Cuba.

9:11So the oil embargo, the sanctions policy that's been wielded in Cuba, the messaging from John Ratcliffe and others about what military threat might be there. I'm curious what your assessment is of how much that's advancing the administration's goals here of getting regime change in Cuba. This is a problem we've seen around the world with sanctions, which is that they impose economic pain, but the ability of regimes to find ways around them and find ways to survive, even as the population suffers in misery. Cuba endured this incredibly harsh and dire economic environment in the 1990s after the end of Soviet support and the economy shrank by a third.

9:55People point to the 1990s, this decade-long special period, as it's called, in terms of pointing out how much economic pain the regime is willing to endure or is willing to impose on Cuban citizens in order to stay in power. That's part of the concern here is, do you squeeze things so much? Do things become so bad that you have a humanitarian crisis that prompts people to leave the island 90 miles off Florida's coast? And now you have a crisis of undocumented migrants coming to the U.S. We've already seen about 20 percent of Cuba's population, several couple million people who have left the island in recent years because of the lack of opportunity, lack of hope and an ability to envision the future.

10:49Cubans became one of the largest groups arriving as undocumented migrants to the U.S. southwest border. And so do these sanctions actually make things so bad that it spurs a very immediate national security threat in terms of overwhelming U.S. shores with migrants? Do we have a sense of how Cubans are responding? Well, we have seen sporadic protests on the island. We've seen in one location that the Communist Party headquarters got attacked. We've seen people setting fires and otherwise creating unrest in the streets in recent months. But it's hard to overstate the repressiveness of the regime and their ability to muzzle these kinds of popular outcries.

11:36This is a regime that for more than six decades has had a high degree of visibility into people's lives, ability to spy on people, encourage people to turn in their neighbors who they think are being disloyal to the revolution. And so despite the suffering on the island, the regime has shown itself effective in the past in being able to maintain control in spite of conditions that in a lot of countries would spur people to rise up or to protest in more visible ways. As we look ahead to what might happen here, obviously, you had what happened in Venezuela, the war in Iran continues. Does the U.S.

12:21have the bandwidth at this moment in time to take military action on Cuba? Well, part of that is a political question in terms of how the Iran war and the efforts to bring it to a resolution are being perceived. And of course, we have midterm elections in the U.S. in early November. We've seen polling that shows the Iran war is unpopular. So part of this is a political question about how much can the American electorate tolerate in terms of foreign entanglements. When we come back.

13:05Eric Martin takes us along as he travels to Venezuela to see what's changed since the U.S. removed the country's president.

13:18The thing about AI for business, it may not automatically fit the way your business works. At IBM, we've seen this firsthand. But by embedding AI across HR, IT, and procurement processes, we've reduced costs by millions, slash repetitive tasks, and freed thousands of hours for strategic work. Now we're helping companies get smarter by putting AI where it actually pays off, deep in the work that moves the business. Let's create smarter business. IBM. Everyone has been there. Your team's feedback is scattered across emails, chats, and sticky notes. It's a mess. But PDF Spaces and Adobe Acrobat gives you one collaborative workspace to streamline every file and comment.

14:02So if you need six departments to finally agree on a proposal, do that with Acrobat. Need to turn a mountain of feedback into one plan of action? Do that with Acrobat. Want to stop searching for files and finally get everyone on the same page? Do that. Do that. Do that with Acrobat. Learn more at adobe.com slash do that with Acrobat. As industries evolve faster than ever, companies need an environment that accelerates strategic growth and Michigan delivers on that promise. From emerging startups to global enterprises, Michigan offers what executives value most, a resilient, innovative ecosystem, Diverse communities that attract top talent and a quality of life that supports work-life balance.

14:45With our unified Team Michigan approach, businesses scale faster and compete at the highest level. Michigan, pure opportunity. Seize your opportunity at michiganbusiness.org.

15:06On April 30th, passengers on American Airlines Flight 3599 left Miami for Simone Blvd International Airport outside Caracas. It was the first commercial flight from the U.S. to Venezuela since 2019. Bloomberg's Eric Martin was one of the passengers. We took off from Miami to a lot of festive atmosphere. They had a big archway of balloons in Venezuela's yellow, blue and red flag colors, traditional Venezuelan food, arepas. We also, President Densi Rodriguez and the government of the Bolivar Republic of Venezuela, you are very welcome to Caracas. Travelers from the U.S. to Venezuela used to have to go through third countries like Panama.

15:55But the U.S. State Department took the country off its do not travel list in March. And now American Airlines is offering two daily flights from Miami. And United Airlines announced plans to start operations to the country from Houston this summer. It's one of the most visible ways yet that we've seen in terms of creating this image of a return to normal, a return to pre-Maduro or pre-Chavez days. But still, there are Venezuelans in exile who live in fear of the government and are afraid that if they went back to their country, they would be arrested and thrown in jail. Eric, you've written about frustration over wages and living conditions, the price of a cup of coffee increasing sixfold in just one year.

16:40Venezuela still has one of the world's highest inflation rates, over 600 percent in April. Talk a bit about this disconnect, the way that things are on the ground versus this perception that it's once again open for business. People are still upset about the low wages, low incomes for people in Venezuela. There's this big disconnect between hope for the future, which people have now in a way that they didn't have nearly as much before January 3rd. and the experience of the current reality, which is while you have companies who are down there and they're exploring and you have some of the first investments and you have lots of money that is coming into the U.S.

17:29Treasury Fund and going to the government to pay services and to pay social services in Venezuela, that this economy that has been declining for years can't be just turned around in, you know, a bit less than five months since the removal of Maduro. President Trump on January 3rd talked about the U.S. will be running Venezuela, prompted many questions about exactly what does that mean. And my reporting has been that the regime really is being responsive to a lot of the demands and the orders being sent from Washington as to what policies to adopt, what decisions to take. The Trump administration has reopened its embassy in Venezuela and reestablished diplomatic relations as well.

18:14To what degree is this a country open for business? Who is investing there? What kind of investments are being made? Well, we've started to see mainly independent oil companies and miners, gold we've seen. We've also seen exploration interest in producing coal. it was venezuela was always a commodity driven economy that was in some ways both the blessing and the curse of venezuela when you're living large it's easy to not plan for a rainy day and that's been a problem for venezuela ran into financial fiscal problems uh in the uh the 1980s 1990s but at the same time these oil companies are careful about what they're going to do we've seen Chevron getting more involved because they have a history in Venezuela.

19:07They've been one of the few that have been able to maintain production in recent years, but others who are more cautious and are a bit skeptical about getting back into Venezuela, given limited resources for them globally and capital and given all kinds of competing opportunities around the world. We've seen President Trump talking about billions of dollars that would go back into Venezuela. And thus far, we've seen a fraction of that, although those decisions also take time and companies do their due diligence. But there's a bit of a catch-22 at work here, which is that there are some investors who say they're not going to feel comfortable investing until there is a real reform of the political system and until there's elections and the transition to democracy and greater transparency of the rule of law.

20:00They've passed an important hydrocarbons law. They've done some reforms to make it more investor-friendly. But I was speaking with someone down there who said, listen, what's happened so far domestically in Venezuela, none of it is our changes that could not be at some point reversed if the dynamic changes. And the only way that you get truly solidifying all of the changes is if the country returns to democracy in a way that investors can trust and in a way that investors see the rule of law. And the big open question is how quickly can that be reasonably done? Are we talking about a period of a few months or more likely a year or a couple of years?

20:47We actually met Delcey Rodriguez very briefly, and one of my colleagues said, President Rodriguez, when will there be elections in Venezuela? And she answered in English. I don't know. Sometime. She said, I don't know. Sometime. And that was kind of a tell as to the strategy for the current government, which is largely still a post-Maduro government. The thing a lot of people are looking for is when will it be a transition not in just the individuals running the country, but more of a cultural transition from the current regime. Eric, let me ask you lastly what the lesson here is for Cuba and its future as it looks to what's going on in Venezuela.

21:36Obviously, there are a lot of differences in these two countries, but how are you looking at them side by side moving forward? I think Maduro's removal from Venezuela has widened the Overton window of outcomes that we can expect from U.S. foreign policy and also from missions that U.S. foreign policy would undertake. Like, even as the U.S. was amassing naval assets and military assets in the Southern Caribbean in the final months of 2025, there were plenty of people who said this was all saber rattling. This was all for show. The U.S. is never going to act against Venezuela. They're looking just to cut a deal.

22:17And the point that's been underlined for me many times by people in the Trump administration is that Trump prefers diplomacy. He would prefer to make a deal, but he's not afraid to use force. And the attacks on Venezuela to remove Maduro, the bombing campaign and the war begun in Iran in late February is another data point. Last June's bombing of Iran's nuclear sites is yet another data point. And essentially the message from these people in the administration is take seriously the threat of using force to achieve foreign policy outcomes. So I think that's the message that I hear most frequently in my reporting.

23:04And I think it's the message that Director Radcliffe sent to Cuba when he was there.

23:14This is The Big Take from Bloomberg News. I'm David Gurra. To get more from The Big Take and unlimited access to all of Bloomberg.com, subscribe today at Bloomberg.com slash podcast offer. If you like this episode, make sure to follow and review The Big Take wherever you listen to podcasts. It helps people find the show. Thanks for listening. We'll be back tomorrow.

23:47but because their policies quietly excluded what happened. Insurers know every detail. Policyholders rarely do. That's why My Policy Advocate exists. For just 27 cents a day, their platform reads your policies and explains where you are vulnerable. They don't sell insurance. They deliver transparency. Before you trust your policy to protect you, let My Policy Advocate tell you what it really says. Go to MyPolicyAdvocate.com. This dog salon? Operational excellence. Thanks to Genius from Global Payments. Scheduling, personalized. Checkouts, instant. Absolutely genius. Big League reliability for any business.

24:26That's genius. From coast to coast, unlock adventure at Red Lion Hotels by Sinesta, where restful sleep, friendly service, and trusted local knowledge are part of every stay. Red Lion makes it easy to feel welcomed, comfortable, and connected wherever the road takes you. Whether you're traveling for business or pleasure, you can spend less and make more of every trip. When you sign up for Sinesta Travel Pass, you'll get their best rates instantly. Go to Sinesta.com to book your stay and unlock the best rates with Sinesta Travel Pass. Here today, roam tomorrow. Join now at Sinesta.com. Terms and conditions apply.