What Are Trump’s Plans for Cuba?

Summary

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WSJ What’s News – “What Are Trump’s Plans for Cuba?”

Date: May 29, 2026
Host: Luke Vargas (The Wall Street Journal)
Guest: Ben Hirons (Intelligence Analyst, Dragonfly Intelligence)

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Episode Overview

This episode of WSJ’s What’s News provides a deep dive into the current U.S. diplomatic and military options regarding Cuba under the Trump administration. The central focus is on the increasing pressure campaign on Havana—legal, diplomatic, and potentially military—in response to alleged threats and foreign influence on the island. Luke Vargas interviews intelligence analyst Ben Hirons to evaluate how far the U.S. is willing to go, what signals to watch, and the likelihood of escalated action.

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Key Discussion Points & Insights

1. News Headlines Rundown (00:09–05:43)

• Blue Origin Rocket Explosion:
  A major setback for Jeff Bezos’ space company—no casualties, but satellite launches delayed for Amazon and NASA.
• Disney and FCC Conflict:
  Disney’s ABC forced to renew broadcast licenses early amid FCC suspicion of biased content—Disney claims Trump administration interference.
• CBS News Shakeup:
  Reorganization at CBS News raises questions of censorship and political pressure inside the newsroom.
• Costco and Dell Financials:
  • Costco: Surge in customers seeking cheaper gas amid an energy shock ([03:27], Gary Millerchip: “A lot of members are increasing their frequency of visiting the gas station… because of the concern about what might the gas price be tomorrow.”)
  • Dell: AI revenue soars, bolstered by Pentagon contracts and investments linked to President Trump’s portfolio ([04:00–04:26]).
• Robinhood Launches AI Agents:
  Customers can now assign trades and some credit card functions to AI bots, signaling mainstream adoption ([05:02], Reporter Hannah Aaron Lang: "The core of the business is still trading... the more customers trade... the more money that Robinhood makes, whether that’s the customer... or an AI agent doing it for them.”)

2. Main Segment: U.S. Pressure and Plans for Cuba (06:18–12:14)

a. Spectrum of U.S. Military Options (06:37–07:11)

• Ben Hirons outlines four potential courses of action if the U.S. chooses military involvement:

  1. Targeted airstrikes (on leaders/military sites)
  2. Operation to capture leaders (like the Maduro operation)
  3. Backing an exile-led ground offensive
  4. Full-scale U.S. military invasion

• Most Likely Option:
  Any strategy that forcibly removes Cuba’s leaders (seen as uncompromising by the U.S.), while avoiding U.S. troop casualties and mass migration, is considered most probable.

  “Any option that avoids risking the lives of US troops and avoids a bout of instability... would be the most likely option.”
  — Ben Hirons ([07:11])

b. Precedents & Preferred Approaches (08:12–08:46)

• U.S. has set a template with Venezuela and Iran: Target leaders, not whole regimes, to coerce systemic change through limited intervention.

• “A similar operation potentially in Cuba would probably target the leadership... the U.S. 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.”
  — Ben Hirons ([08:12])

c. Recent U.S. Preparations and Escalation Signs (08:55–10:27)

• Legal Justification:
  The U.S. criminally charged ex-President Raul Castro, echoing tactics used pre-Maduro campaign.

  “It’s formed a legal basis... by criminally charging former President Raul Castro... the U.S. used similar charges against Maduro to justify that operation...”
  — Ben Hirons ([09:12])

• Intel on Arms/Foreign Presence:
  • Reports of Cuba acquiring ~300 drones from Russia/Iran, allegedly dispersed around the island.
  • U.S. alarm over a tripling of Russian/Chinese intelligence staff in Cuba since 2023.
• Shifting U.S. Rhetoric:
  • Sharper criticism from U.S. officials, especially Marco Rubio and the recent CIA director’s visit to Havana.
  • More overt threats about military consequences if diplomacy fails.

d. What to Watch Next: Signs of Escalation (10:27–12:07)

• Indicators that Military Action Is Imminent:

  • More explicit public warnings and critiques of Cuba.
  • Allegations of Russian/Chinese meddling, drone capabilities, appeals to historical U.S.-Cuba grievances.
  • Formal U.S. abandonment of diplomacy (e.g., raising travel advisories, declaring Cuban airspace closed).
  • Military Movements:
    U.S. build-up near Cuba would be highly visible, but isn’t considered necessary due to Cuba’s proximity; monitoring carrier strike group locations remains telling.

• Element of Surprise:
  U.S. wants to keep tactical details secret while clearly signaling readiness to act.

  “It would not necessarily be obvious that the US has abandoned diplomacy... it's a negotiating tactic to intimidate... [while] more obvious ones [would be] military build-ups or travel advisories."
  — Ben Hirons ([10:42])

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Notable Quotes & Memorable Moments

• “The template here is in Venezuela and Iran already the US Mounted operations to target leaders in those countries... so a similar operation potentially in Cuba would probably target the leadership.”
  — Ben Hirons ([00:27], [08:12])
• “A significant chunk of Robinhood's business comes from something called payment for order flow... the more customers trade... the more money that Robinhood makes, whether that's the customer... or an AI agent doing it for them.”
  — Reporter Hannah Aaron Lang ([05:02])
• “Any option that avoids risking the lives of US troops and avoids a bout of instability on the island that would potentially trigger migration towards the US would be the most likely option.”
  — Ben Hirons ([07:11])
• “It’s formed a legal basis for potential military operations in Cuba by criminally charging former President Raul Castro...”
  — Ben Hirons ([09:12])
• “It would not necessarily be obvious that the US has abandoned diplomacy and decided to take military action... the Trump administration wants to use the element of surprise... but not necessarily conceal its willingness to use military action.”
  — Ben Hirons ([10:42])

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Timestamps for Key Segments

• 00:09–05:43: Top headlines (Blue Origin, Disney, CBS News, Costco/Dell/Robinhood updates)
• 06:18: Segment intro: U.S.-Cuba pressure campaign
• 06:37–07:11: Four potential military options against Cuba
• 07:11–08:46: Assessment of likely scenarios; comparison to Venezuela/Iran
• 08:55–10:27: Legal, intelligence, and rhetorical escalation against Cuba
• 10:27–12:07: What signs signal imminent U.S. action
• 12:07–12:14: Segment wrap-up

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Conclusion

This episode contextualizes heightened U.S. pressure on Cuba in 2026, offering listeners a framework to interpret current events and government statements as either negotiating tactics or genuine steps toward intervention. Analyst Ben Hirons situates Cuba within Trump-era precedents set in Venezuela and Iran, highlighting an increasingly direct U.S. posture but also significant caution and a clear preference to avoid direct military entanglement unless unavoidable.

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Transcript

[Ben Hirons]

Sponsored by Wellington Management, pioneering investment strategies

[Interviewer/Host]

for nearly 100 years.

[Reporter Hannah Aaron Lang]

Visit Wellington.com USAWealth

[Luke Vargas]

A Rocket Explosion deals a setback to Jeff Bezos 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.

[Ben Hirons]

The 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.

[Luke Vargas]

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 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 Glenn 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 initiat. 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 Kimmel Live 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 shakeup of CBS News, the network has appointed New York Times columnist Nick Bilton as the next executive producer of its Story 60 Minutes program and cut ties with correspondents Sharon Alfonsi and Cecilia Vega. In December, Alfonsi 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 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 millerchip predicted that an uptick in traffic to the company's gas stations would fuel future sales.

[Gary Millerchip]

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.

[Luke Vargas]

Costco shares were flat following the report. Well, not so for Dell, which saw its shares jump nearly 40% 40% off hours.

[Interviewer/Host]

That's after the computer hardware maker reported

[Luke Vargas]

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 shares have risen about

[Interviewer/Host]

150%

[Luke Vargas]

and trading platform Robinhood is launching new features to let users hand over 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 a trading agents are hitting the mainstream.

[Reporter Hannah Aaron Lang]

In spite of the many ways that Robinhood has expanded their business in recent years, the core of the business is still trading. A significant chunk of Robinhood'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 Robinhood 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 Robinhood platform.

[Luke Vargas]

Coming up, as the US 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.

[FTI Consulting Announcer]

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[Luke Vargas]

Is the US laying the groundwork for

[Interviewer/Host]

military action against Cuba? Our Dow Jones colleagues over at Dragonfly

[Luke Vargas]

Intelligence have been monitoring the likelihood of

[Interviewer/Host]

that as the Trump administration tight the screws against Havana. And America's intelligence analyst Ben Hirons joins me now to discuss where the situation is headed.

[Luke Vargas]

Ben, earlier this month your team sketched

[Interviewer/Host]

out a few different courses of action. 4 In fact, should the US decide to conduct military action against Cuba, which is an important caveat to all of this. 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 regime exiles and finally a large scale US military invasion. This is quite the spectrum of possibilities here. Where do those rank currently in terms of likelihood?

[Ben Hirons]

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 an 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's current leaders who Washington considers uncompromising, any option that avoids risking the lives of US troops and avoids a bout of instability on the island that would potentially trigger migration towards the US would be the most likely option.

[Interviewer/Host]

So let's eliminate those biggest risks. Loss of US life or wild instability that creates an exodus that would probably, probably lower down the likelihood of a large scale US military invasion or maybe a revolt by anti regime exiles.

[Ben Hirons]

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 Nicolas Maduro's vice president. It hasn't completely changed the regime. And so our understanding of that, 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.

[Interviewer/Host]

You mentioned some preparations earlier in the event that diplomacy doesn't work out.

[Luke Vargas]

Tell us more about what those look

[Interviewer/Host]

like and whether they're US preparations, Cuban ones.

[Ben Hirons]

So there's three key developments that we've seen in recent weeks that suggest the US 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 of

[Interviewer/Host]

May, something they did, notably several years before. The operation against Maduro.

[Ben Hirons]

Exactly. The US 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 US in Cuba would be focused on capturing or killing Raul Castro. A couple more recent developments. 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 U.S. officials claim that the Cuban government has hidden them across the island and discussed 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 US officials has changed. Marco Rubio has particularly been at forefront of this. He released a video criticizing the regime calling for change, and the visit of the CIA director to Havana was key. The US 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.

[Interviewer/Host]

Ben, in terms of what we should be watching for in the days and weeks to come, 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.

[Ben Hirons]

Yeah. It would not necessarily be obvious that the US has abandoned diplomacy and decided to take military action. The first is US 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 it has abandoned diplomacy, raising its travel advisory level for the country, declaring that Cuba's airspace is shut, as it did with 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 used that military presence nearby as a negotiation. So I'd be watching where U.S. carrier strike groups are around the world closely.

[Luke Vargas]

Ben Hyhorns is an America's intelligence analyst at Dragonfly Intelligence. Ben, thank you so much for stopping by.

[Ben Hirons]

Thank you.

[Luke Vargas]

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 Street Journal.

[Interviewer/Host]

We will be back tonight with a new show. Otherwise, have a great weekend and thanks for listening.

[Gary Millerchip]

Foreign.

[FTI Consulting Announcer]

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