WSJ What’s News - What Are Trump’s Plans for Cuba?

Episode Date: May 29, 2026

A.M. Edition for May 29. A Blue Origin rocket explodes on its Florida launchpad, dealing a setback to Jeff Bezos’ space company. Plus, the Iran war energy shock sends drivers flocking to Costco gas stations. And with the U.S. intensifying its pressure campaign on Cuba, indicting Raúl Castro and warning of an increase in Russian and Chinese operations on the island, Dragonfly Intelligence analyst Ben Hiorns discusses whether U.S. military action could be in the cards. Luke Vargas hosts. Sign up for the WSJ’s free What’s News newsletter. Learn more about your ad choices. Visit megaphone.fm/adchoices

Nearly home. Isn't home where we all want to be? Riba here for Realtor.com, the pro's number one most trusted app. A dream home isn't a dream home if it comes with a nightmare commute. That's why realter.com has real commute, so you can search by drive time. Download the realtor.com app today because you're nearly home. Make it real with realtor. Pro's number one most trusted app based on August 2025 proprietary survey.

A rocket explosion deals a setback to Jeff Bezos's blue origin. Plus, the Iran War energy shock sends drivers flocking to Costco gas stations and will survey Washington's options if its Cuba diplomatic pressure campaign fails to dislodge the island's regime. The template here is in Venezuela and Iran already. The U.S. mounted operations to target leaders in those countries, military assets, air bases. And so a similar operation potentially in Cuba would probably target the leadership. It's Friday, May 29th. I'm Luke Vargas for the Wall Street Journal. And here is

the AM edition of What's News, the top headlines and business stories moving your world today. We begin in Florida, where a rocket being tested by Jeff Bezos's blue origin exploded on a launch pad overnight, sending an enormous ball of fire into the sky. A spokesman for the Space Force, which oversees the site of the explosion near Cape Canaveral, said there were no injuries or fatalities. The incident involved one of Blue Origin's powerful New Glen Rockets, which was being prepared for an upcoming mission after a previous launch earlier this year deployed a satellite into the wrong orbit.

The explosion is certain to delay upcoming satellite launches for Amazon and potentially push back other flights, including for NASA. Disney's ABC has complied with an FCC order to apply for early renewals of broadcast licenses for eight of its local stations, but in a strongly worded filing said it was doing so under protest. FCC chairman Brendan Carr has called for the early renewals, in part because he believes that Disney hasn't been totally forthcoming in response to requests for information about its DEI initiatives. Disney, meanwhile, has said the car is targeting ABC in order to suppress content that the Trump administration finds objectionable. Both The View and Jimmy Kim alive have long been sharply critical of Trump

and his administration. Requesting early renewals is often seen as a sign that the FCC is preparing to challenge an owner's fitness to hold a broadcast license. In editor-in-chief Barry Weiss's latest shake-up of CBS News, the network has appointed New York Times columnist Nick Bilton as the next executive producer of its storied 60 Minutes program and cut ties with correspondence Sharon Alfonzi and Cecilia Vega. In December, Alfonzi challenged Weiss's decision to hold a 60-minute segment on an El Salvador prison where the Trump administration had sent Venezuelan migrants, and she said in a statement yesterday that the network's decision to let her contract expire was a punishment for that resistance. In her own statement, Vega accused CBS of censorship,

saying that producers had faced pressure to, quote, insert political bias into our stories. A CBS news spokesman said those claims were not based in reality. In markets news, Costco says that more inflation-weary customers are visiting its stores, driving a sales beat in its fiscal third quarter. While higher costs did pinch Costco's margins, CFO Gary Miller-chip predicted that an uptick in traffic to the company's gas stations would fuel future sales. A lot of members are increasing their frequency of visiting the gas station to top up in between. what would have normally been a gap between getting the tank to empty because of the concern about what might the gas price be tomorrow. But we do think over time it's a great way to build loyalty. When we look at our members that are engaged in gas with us, they are generally

visiting more frequently overall. They're spending more with us overall, and they're also renewing at a higher rate. Costco's shares were flat following the report. Well, not so for Dell, which saw its shares jump nearly 40% off hours. That's after the computer hardware maker reported a 144% jump in full-year AI revenue on the back of red-hot demand for its AI-optimized servers. The company also scored a five-year Pentagon contract this week as the DOD restructures its digital systems. The contract follows the disclosure of large purchases of Dell stock earlier this year by President Trump's money managers. Since then, Dell's shares have risen about 150%. And a trading platform Robin Hood.

is launching new features to let users handover trading decisions to AI agents. That includes allowing customers to connect agentic tools like Claude or Cursor to a virtual version of their gold credit cards, which could then make online purchases, reservations, or book travel. And while executives say that only stock trades are on the table for now, with options and crypto trading to come later, reporter Hannah Aaron Lang said the rollout signals that AI trading agents are hitting the mainstream. In spite of the many ways that Robin Hood has expanded their business in recent years, the core of the business is still trading.

A significant chunk of Robin Hood's business comes from something called payment for order flow, which essentially means that the more customers trade, you know, stocks, options, cryptocurrencies, the more money that Robin Hood makes, whether that's the customer, you know, placing the trade themselves and hitting the buy button or, you know, an AI agent doing it for them. And then I imagine there's a broader goal to this as well, which is to continue being one of the first well-established brokerage firms to offer AI capabilities and therefore bring more traders to the Robin Hood platform. Coming up as the U.S. intensifies its Cuba pressure campaign, indicting its former leader and warning of foreign intelligence operations on the island, we'll look at whether military action against the country could be in the cards. That's after the break. In a world full of noise, long-term thinking stands out. On the Capital Ideas podcast, Capital Group leaders explore the decisions that matter most in investing, leadership, and life. It's a rare look inside a firm that's been helping people pursue their financial goals for more than 90 years. Listen to the Capital Ideas podcast from Capital Group, published by Capital Client Group, Inc.

Is the U.S. laying the groundwork for military action against Cuba? Our Dow Jones colleagues over at Dragonfly Intelligence have been monitoring the likelihood of that as the Trump administration tightens the screws against Havana. And America's intelligence analyst Ben Huyarns joins me now to discuss where the situation is headed. Ben, earlier this month, your team sketched out a few different courses of action for, in fact, should the U.S. decide to conduct military action against Cuba, which is an important caveat to all of But those four courses were targeted airstrikes. These would be against Cuban leaders or military sites, an operation to capture Cuban leaders, kind of a Maduro rerun, backing a ground offensive

that would be carried out by anti-regime exiles. And finally, a large-scale U.S. military invasion. This is quite the spectrum of possibilities here. Where do those rank currently in terms of likelihood? So it's important to say that we have not seen sufficient evidence to say with high confidence that the US is moving towards a military attack against Cuba. The US priority seems to be to use its ongoing fuel blockade and back channel diplomacy to reach a agreement with the regime. That said, the US is definitely making preparations and considering its options in the event that it abandons diplomacy and no longer considers a deal possible. That means it is possible to rank these in terms of relative likelihood. And our understanding of the Trump administration's

thinking suggests that any option that results in the removal of Cuba, Cuba's current leaders, who Washington considers uncompromising, any option that avoids risking the lives of U.S. troops, and avoids a bout of instability on the island that would potentially trigger migration towards the U.S. would be the most likely option. So let's eliminate those biggest risks, loss of U.S. life or wild instability that creates an exodus. That would probably lower down the likelihood of a large-scale U.S. military invasion or maybe a revolt by anti-regime exiles. Exactly. And the template here is in Venezuela and Iran already. The US mounted operations to target

leaders in those countries, military assets, air bases. And so a similar operation, potentially in Cuba, would probably target the leadership. As it's clear in Venezuela, the Trump administration is working with Nicholas Maduro's vice president. It hasn't completely changed the regime. And so our understanding of that thinking that goes behind that is that the US would take a similar approach to Cuba, where it's focused on eliminating certain leaders and then encouraging the rest of the government to cooperate. You mentioned some preparations earlier in the event that diplomacy doesn't work out. Tell us more about what those look like and whether there are U.S. preparations, Cuban ones. So there's three key developments that we've seen in recent weeks

that suggest the U.S. is potentially moving towards military action. The first key one is that it's formed a legal basis for potential military operations in Cuba by criminally charging former president Raul Castro on the 20th May. Something they did notably several years before the operation against Maduro. Exactly. The U.S. used similar charges against Maduro to justify that operation, which it framed as a law enforcement operation. And this would potentially suggest that any operation of the U.S. in Cuba would be

focused on capturing or killing Raul Castro. A couple more recent developments. The U.S. officials have shared intelligence with journalists about activities in Cuba, to do with Cuba acquiring drones from Russia and Iran, about 300 military drones. The US officials claim that the Cuban government has hidden them across the island and discuss plans of how to retaliate against the US in the event of an attack. And the other is that US officials have claimed that Russia and China have tripled the number of intelligence personnel at electronic eavesdropping facilities in Cuba since 2023,

which the US considers a threat as well. And then also another key development is that the rhetoric from U.S. officials has changed. Marco Rubio has particularly been at the forefront of this. He released video criticizing the regime, calling for change, and the visit of the CIA director to Havana was key. The U.S. seems to be more direct in its threats towards Cuba now, warning that military action is a possibility if they do not reach a deal. Ben, in terms of what we should be watching for in the days and weeks to come? I mean, what steps have we notably not seen yet? Were, let's say, a military course of action sort of starting to become the consensus way forward in Washington?

Yeah, it would not necessarily be obvious that U.S. has abandoned diplomacy and decided to take military action. The first is U.S. rhetoric towards Cuba. Based on what happened with Venezuela and Iran, the Trump administration wants to use the element of surprise in terms of a specific operation, but it does not necessarily want to conceal its willingness to use military action. It's a negotiating tactic to intimidate. So more explicit warnings, accusations about Russian and Chinese influence on the island, Cuba's drone capabilities, even historical grievances related to the Cuban Revolution. That's something we saw with Venezuela, talking about oil. And then more obvious ones, the US declaring that has abandoned diplomacy, raising its travel advisory level for the country, declaring that Cuba's airspace is shut, as it did

Venezuela. And the second thing would be military movements, right? The US has a large military presence already in the Caribbean, but it's not really comparable to what it had before its action in Venezuela and in Iran. But a big buildup near the island would indicate that the US is getting ready for a military operation. I'd say a caveat to this, though, is that Cuba is very close to the US. The US would not necessarily need aircraft carriers nearby to mount an operation there. They could fly from southern states in the U.S. This strategy, though, would divert from what they did in Venezuela and Iran, where they use that military presence nearby as a negotiation. So I'd be watching where U.S. carrier strike groups are around the world closely. Ben, High Orn's, is in America's

intelligence analyst at Dragonfly Intelligence. Ben, thank you so much for stopping by. Thank you. And that's it for what's news for this Friday morning. Today's show was produced by Hattie Moyer. Our supervising producer was Daniel Bach, and I'm Luke Vargas for the Wall Journal. We will be back tonight with a new show. Otherwise, have a great weekend, and thanks for listening. The Madamy Holmes Bike for Brain Health supporting Baycrest returns on May 31 for its fifth anniversary with a new start and finish at the Aga Khan Museum. Join thousands of cyclists as we take over the DVP and Gardner Expressway in support of dementia research and brain health. Riders of all abilities are welcome, and both regular bikes and e-bikes can participate. Bring your friends, family, or

corporate team and make an impact. Register today at fight for brainhealth.ca.