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What’s a bored Donald Trump to do? Apparently, target Cuba

May 12, 2026
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What’s a bored Donald Trump to do? Apparently, target Cuba
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Donald Trump is “bored” with his war of choice in Iran. That’s according to the Atlantic’s Jonathan Lemire, who recently reported that after operations “proved far more difficult and lasted far longer than he expected,” the president wants to “move on.” Ending America’s war with the Islamic Republic has turned out to be beyond Trump’s skills as an allegedly brilliant negotiator, whose only strategy is to bully and sue if he doesn’t get his way, and his two “peace envoys,” Jared Kushner and Steve Witkoff, have also come up short. Trump wants quick “victories” and the Nobel Peace Prize, so he’s trying to manifest a victory by simply saying there is one. But Iran has Trump backed into a corner, and there’s no way out. 

The central problem is that Trump thought the Iranians would, in his words, “cry uncle” after he and Israeli Prime Minister Benjamin Netanyahu launched the first air assault on Feb. 28, apparently not realizing that the Islamic Republican Guard Corps would double their resolve to fight back. To use another of Trump’s terms, they had no idea how many cards Iran had to play. 

Most analysts of the region did understand, which is why the U.S. never succumbed to the entreaties over the past 47 years by the likes of Netanyahu and war hawks in Congress, such as Sen. Lindsey Graham, R-S.C., to attack the country. They understood that Iran could strangle the global oil supply by closing the Strait of Hormuz, and it’s been clear for some time that Iran had the capability of endangering oil production facilities all over the region with their drones and missiles. This is one reason why American allies like Saudi Arabia are starting to panic that the U.S. is opening them up to even more destruction. 

Iran still has that card up its sleeve, but everyone knows it’s there because they showed it back on March 18, when Israel pushed the envelope and bombed one of Iran’s biggest gas fields and Iran retaliated by damaging the world’s largest natural gas export plant in Qatar that will take years to repair. After that Trump declared a ceasefire that required minimal concessions from Iran. That was pretty much when it was all over. 

Robert Kagan in the Atlantic pointed out that even if Trump were to follow through on his threat to end Iran’s civilization with a massive bombing campaign or hit them as a parting shot before leaving the region, the Islamic Republic has shown they have the willingness and capacity to go out in a blaze of glory — and catastrophically cripple the world’s energy supply. As Kagan put it, “if this isn’t checkmate, it’s close.”

So what’s a bored, frustrated president to do? Trump knows by now he can’t bomb his way to victory, and it doesn’t look like his blockade is making any difference. He can just leave and say he won, but unless the strait is open even he can’t sell that lemon, not even to the MAGA faithful, and not with gas prices hitting a national average of $4.52 — and rising above five dollars in Nevada, Oregon, Washington state, Alaska and Hawaii, and more than six dollars in California.

But Trump may have an audacious plan: yet another military operation, but one that would be much closer to home. 

That may sound barmy, what with all the ships being deployed in and around the Arabian Sea for weeks already, and reports that the military is running out of munitions. But CNN is reporting that there has been a steep increase in military intelligence-gathering flights over Cuba. 

Now, the thinking seems to go, an invasion of Cuba could be just the ticket to remind the world of his strength — and to distract from his failure in Iran.

Trump has been talking about invading and occupying Cuba for months, but that prospect has seemed less likely as the quagmire in Iran has developed. His eagerness to take action against the island nation was more or less a holdover of the giddy days in January when the U.S. was kidnapping Venezuela’s president and taking over their oil fields with no resistance. Trump apparently thought that operation went so smoothly because everyone was awestruck by his manly power and strength, and that he’d been foolish to avoid war all this time. It was easy! Now, the thinking seems to go, an invasion of Cuba could be just the ticket to remind the world of his strength — and to distract from his failure in Iran. 

The president has said publicly that he would have “the honor of taking Cuba,” and with the U.S. running a blockade on the country for months, to all intents and purposes it has already taken military action there. On May 1 he said he was considering sending the USS Abraham Lincoln to Cuba to force an immediate surrender. It’s currently in the Arabian Sea, but he seems to think it could make “ a little excursion” to topple the government and take it over. Trump even said as much — that it could “come in, stop about 100 yards offshore, and they’ll say: ‘Thank you very much. We give up.’

Want more sharp takes on politics? Sign up for our free newsletter, Standing Room Only, written by Amanda Marcotte, now also a weekly show on YouTube or wherever you get your podcasts.

As Axios noted, Trump and Secretary of State Marco Rubio’s “escalating rhetoric” is raising the possibility of an imminent military operation against Cuba. Then there are their actions.

On May 5, Rubio attended a conference at the military’s Southern Command in Miami, where he and military leaders discussed “efforts to counter threats that undermine security, stability and democracy in our hemisphere.” Considering the dumpster fire that is U.S. foreign policy at the moment one would think Rubio would have more important things to do — that is, unless some kind of military operation is really on the table. Otherwise it would just be a major coincidence that Rubio and Marine Corps Gen. Francis L. Donovan, commander of Southern Command, posed for a photo in front of a map of Cuba.

Two days later, Rubio announced a new round of sanctions against the island that targeted its military and a state-owned energy company. This accompanied the news that the State Department is bolstering a South Florida disaster-preparedness supply center.

The administration no doubt believes the military can execute another Venezuela-style operation, and maybe it can. After suffering from years of economic hardship that has been made worse under the American blockade, Cuba is weak. It certainly wouldn’t be too hard to take the country. The real question is what happens then. 

“[Trump’s] done regime change in two nations, and hard-liners are still running things,” Sen. Tim Kaine, D-Va., told MS NOW recently after another war powers resolution aimed at limiting Trump’s authority to use military action, including in Cuba, was defeated in the Senate. “So it’s not like he has produced a Venezuela for Venezuelans or an Iran for Iranians. The U.S. has a very poor track record of successfully executing regime change, particularly in the Americas.”

It’s unclear who would be running Cuba. There has been talk of making Rubio president, although Trump has said that he would actually be the “acting president” after they go in, a job he would no doubt relish. The general contractor in chief could really sink his teeth into rebuilding that little island country in his image. I’m sure they could use a big beautiful ballroom.

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