⚡ Axios AM: Trump's Cuba war games

☕ Happy Thursday! Smart Brevity™ count: 1,347 words ... 5 mins. Thanks to Noah Bressner for orchestrating. Edited by Andrew Pantazi and Bill Kole.

👑 Situational awareness: The "No Kings" movement announced a nationwide day of protests on June 14 — Flag Day and President Trump's 80th birthday — to counterprogram the UFC fight at the White House. More on the protests.

The Trump administration is bracing for the potential collapse of Cuba's totalitarian government as early as this summer, and has war-gamed military response plans in case the island descends into chaos, U.S. officials tell Axios' Marc Caputo.

• Why it matters: President Trump hasn't authorized an invasion and prefers a peaceful transition to a free Cuba. So the administration will keep pushing economic sanctions to try to strangle the regime in Havana in a slow-motion constriction.

"The best way to describe it is 'accelerationism,'" a senior administration official said, referring to hastening societal collapse.

• "But we don't want to kill off the regime just yet. There's a method to this. It's in stages."

🔎 Zoom in: This methodical squeezing of Cuba's communist regime aims to buy time for Trump, engrossed in peace talks with Iran, to eventually focus on Cuba.

• "Iran's not finished, and the president is not in a rush," another senior administration official said. "Trump wants to exhaust all the levers that he can. But at this point, there aren't as many levers as before."
• A third senior administration official said: "We have a pretty deep toolbox, especially when it comes to sanctions and enforcing them. More is on the way."

The big picture: The Cuba operation aims to eliminate the wellspring of Latin American Marxist agitation and anti-U.S. activism, ever since Fidel and Raúl Castro led their successful revolution in 1959.

• To bring Cuba to its knees this year, the administration first targeted the island's lifeline: Venezuela and its socialist leader, Nicolás Maduro, who kept Havana afloat with oil shipments that powered the country and gave it export revenue.

👀 Inside the room: Last month, U.S. Southern Command, which oversees military operations in the Caribbean, held a multiagency "tabletop" exercise to prepare for military action in Cuba, one of the senior administration officials said.

• "Everything is on the table, but no invasion is planned or imminent," the official said. "When POTUS says go, we're ready for anything."

In the exercise, another source said, U.S. officials discussed Cuba's possession of drones and how to respond to possible unrest in the sweltering Cuban heat as spring turns to summer.

• "It's going to be hot," the source said. "People won't have electricity. Food spoils without refrigeration. People get angry. They can take to the streets. And then what happens? I can't see the president doing nothing if there's repression."
• Another source, a Trump adviser, disagreed: "The president does not want boots on the ground for more than 48 hours. It's a quagmire in the making. This could get messy."

One presidential adviser said the approach to Cuba is "classic Trump: Push your enemy off balance. It's pressure, watch the response, apply more pressure, watch the response, apply more pressure."

• One of the officials said: "We have time. The regime doesn't."

Go deeper: 3 crucial differences between Cuba and Venezuela.

CEOs of the world's biggest companies lost confidence in the economy this month as the Iran war drags on, Axios' Emily Peck writes from a new survey of 141 Fortune Global 500 chief executives.

• Why it matters: Business leaders who lack confidence tend to pull back on hiring and investment, weighing down the economy.

🧮 By the numbers: CEO confidence fell 12 points since February to 47, according to the survey from The Conference Board, a nonpartisan think tank, and The Business Council, an association of CEOs.

• 47% of CEOs said economic conditions were worse, up from 8% at the start of the year.
• Only 15% said conditions were better than six months ago, down from 39% in February.

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The Iran war has exacerbated a shortage of missile-defense weaponry that is likely to plague the U.S. and its partners, from Ukraine to Taiwan, for years to come, Axios' Dave Lawler and Colin Demarest write.

• Why it matters: The conflict is draining weapons stockpiles far faster than American factories can replace them, leaving the Pentagon and its allies scrambling to ramp up production and find cheaper alternatives.

The report from the Center for Strategic and International Studies finds the U.S. used so many interceptors from missile defense systems like Patriot and THAAD in the Middle East that stockpiles won't be replenished until 2029.

• And that's if the war doesn't resume.

🧮 The math is stark: The U.S. took delivery of just 172 Patriot interceptors in fiscal year 2026 and has used more than 1,000 in the Iran war, according to CSIS.

• The Pentagon insists it's maintained enough capability to defend the U.S. and prosecute the Iran war.

Keep reading.

Health care can be confusing. UnitedHealth Group is making it simpler with Avery, a new generative AI companion.

Here’s how: Avery helps patients understand coverage, schedule appointments, estimate costs and more.

Learn more.

A record-high 56% of Americans say moral values in the U.S. are "poor," according to a Gallup poll out this morning.

• That's up 12 points from last year.
• 80% say moral values are "getting worse" — 14 points higher than '25.

More from Gallup.

Corporate leaders are starting to question whether soaring AI spending is delivering meaningful returns, Axios' Madison Mills writes.

• Why it matters: Companies that rushed to embrace AI are now confronting ballooning IT costs, uncertain productivity gains and growing employee skepticism.

Uber's COO said AI costs are getting "harder to justify." Microsoft canceled most of its Claude Code licenses, in part over costs, according to The Verge.

• An AI consultant tells Axios one of their clients recently spent half a billion dollars in a single month after failing to put usage limits on Claude licenses for employees.
• Companies are citing AI's ability to automate jobs as a cause for layoffs. Anuj Kapur, CEO of CloudBees, told Axios that workforce cuts may be "the only lever they can pull" to offset their AI bills.

💸 What's happening: The enterprise is undergoing a "healthy swing" away from AI overuse — or "tokenmaxxing," the push to burn as many AI tokens as possible — Ali Ansari, CEO of model training firm Micro1, told Axios.

• He hopes this correction will push companies toward more efficient AI use.

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IBM is investing $5 billion and deploying more than 20,000 engineers to help secure open-source software, Axios' Maria Curi writes.

• IBM CEO Arvind Krishna told Axios he expects the government to be very interested in a solution like Project Lightwell: "We believe that at least some people in the government are looking for the private sector to step up with an answer like this."

Why it matters: AI is supercharging cyberattacks, pushing companies to adopt the same technology to defend against threats.

"Project Lightwell" — the new initiative by IBM and Red Hat, its open source software subsidiary — uses frontier AI capabilities to establish a "clearinghouse" to identify and fix vulnerabilities at scale.

• Krishna said he expects the project to expand beyond the financial sector.

Keep reading.

Former First Lady Jill Biden tells "CBS News Sunday Morning" she was "frightened" by President Biden's 2024 debate performance and thought her husband was having a stroke:

A memoir by Jill Biden, 74, "View From the East Wing," will be out next Tuesday.

• Watch the 30-second clip.

Dolly Parton's rapidly expanding hospitality empire will add a roadside travel stop next month, Axios Nashville's Adam Tamburin reports.

• Dolly's Tennessean Travel Stop opens June 24 in Cornersville, an hour south of Nashville on Interstate 65. It's the first of several planned locations.

🎤 The new travel stop joins Parton's theme park and mountain resort. A new museum and hotel are coming to downtown Nashville later this year.

• Local musicians and bands will provide live entertainment.

Read the announcement ... Share this story.

UnitedHealth Group is expanding access to doula support to make maternity care easier to access and navigate.

Key numbers: Over 7 million people across the country could qualify for the doula support offering by 2027.

Learn more.

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