Hyperextended

By Nick Catoggio

Friday, May 22, 2026

 

I’m excited about our new regime-change operation in Cuba, mostly as a matter of morbid curiosity.

 

Specifically, I’m intrigued to see what happens to an unpopular president’s support when he starts an unpopular war that no one saw coming while struggling to resolve another unpopular war he started that no one saw coming.

 

Having grown bored with the stalemate in Iran, a “frustrated” Donald Trump reportedly complained to advisers this month that the White House’s plan to squeeze Havana into submission is progressing too slowly. He and his team have decided to move things along by dusting off the Venezuela playbook—indicting the enemy’s leader on federal criminal charges as a pretext to remove him, positioning naval assets off its coast to warn its leaders against resisting, and asking everyone to believe that a banana republic that can’t feed its people is a threat to the United States grave enough to warrant immediate military action.

 

That’s going to take a lot of persuasion. Per YouGov, Americans currently split 15-64 on whether the U.S. should go to war with Cuba, with 21 percent undecided. (Among those who take a view one way or the other, 81 percent are opposed.) Meanwhile, disapproval of the Iran War stands at 60 percent, and disapproval of Trump’s job performance is knocking on the door of 60.

 

Rarely, if ever, has America had a president whose own policy priorities have diverged so sharply from those of his constituents, and it’s certainly never had one who cared less about that divergence. That’s why I’m excited: The Cuba takeover will amount to a novel political experiment to gauge how voters react to a democratic leader all but formally notifying them that their opinion no longer matters to him.

 

Although, now that I think about it, I suppose he’s already given that notice.

 

I’m also excited to see the president and his deputies try to explain the dire risk that Cuba allegedly poses to the U.S. That wasn’t hard with Iran given the regime’s nuclear ambitions and decades of menacing its American-allied neighbors; it will be more challenging with respect to the desiccated corpse of Castroism. Stephen Miller tried in an interview this week, warning Fox News viewers that “Cuba, positioned just a 45-minute flight from American shores, has been a staging ground for America's adversaries for decades.” But which adversaries?

 

Russia and China? I’m sorry to have to tell you, but postliberals don’t feel adversarial toward either. And even if the president does, his willingness to accommodate them on their own expansionist priorities should ensure that they’ll make no trouble for him in Cuba.

 

That’s what a “spheres of influence” worldview is all about.

 

There’s one more interesting facet to Trump starting a war with Havana before our war with Tehran is done. It’s the latest confirmation that no matter how much political trouble he encounters from overextending himself, he continues to do it.

 

Battle royal.

 

You would think he might have learned after last year’s “Liberation Day” debacle.

 

Moving forward with tariffs amid an affordability crisis continues to be the biggest mistake of his presidency, but the public might have tolerated levies imposed specifically on nations that have gobbled up American manufacturing (i.e., China). That’s not what Trump did. He tariffed everyone—well, almost everyone—and then had to hit “pause” just a week later after bond markets began to wobble.

 

He overextended himself. Instead of picking a fight whose damage he might have been able to contain, he started a battle royal and was caught off guard by the backlash.

 

The same thing happened recently with Congress.

 

Republicans have narrow majorities in each chamber—53-47 in the Senate and 218-215 in the House, tricky business even for a man who wields cultlike control over his party. Moving legislation with majorities as thin as those requires a deft touch politically. That means not attacking lawmakers whose support you need and not making their lives harder by thrusting them into needless new political controversies.

 

Trump did the opposite. He turned Bill Cassidy into a lame duck who no longer owes him anything, then promptly did the same to John Cornyn. (Assuming Cornyn loses next week’s primary runoff in Texas, that is, which is likely.) And then, with Senate Republicans already seething, he dropped two flaming bags of dog sh-t on their porch, launching a new taxpayer-funded slush fund for his criminal cronies and demanding that lawmakers give him $1 billion for a ballroom while voters are screaming about the cost of living.

 

He overextended himself. He might have gotten away with any one of those provocations, but insisting on a battle royal came back to bite him again. The ballroom funding now appears to be dead, and the slush fund is in deep trouble, with one senator whispering to Punchbowl News, “Our majority is melting down before our eyes.” Things are so bad in the House that GOP leaders had to cancel a war powers vote on the Iran conflict yesterday because Democrats were poised to win it with help from disgruntled moderate Republicans.

 

Now here we are with the president about to overextend himself again, starting a new war before the last one has finished. Although, to be fair, he’s trying hard to wrap things up in Iran before throwing a punch at Cuba.

 

Maybe too hard, it turns out.

 

An overextended military.

 

On Wednesday Axios reported on a phone call between Trump and Benjamin Netanyahu that allegedly left the Israeli prime minister with his “hair on fire.”

 

Details are thin, but the gist of the disagreement is clear. The president wants to sign a deal with the regime that would end the war and “launch a 30-day period of negotiations on issues like Iran's nuclear program and opening of the Strait of Hormuz,” according to the outlet. Netanyahu “wants to resume the war to further degrade Iran's military capabilities and weaken the regime by destroying its critical infrastructure.”

 

Israel’s leader sees what’s coming. The United States is poised to accept a strategic defeat by walking away from the conflict, Robert Kagan explains in a new piece for The Atlantic, and that strategic defeat will empower Iran while isolating Israel.

 

As usual, it comes down to oil. The White House continues to say that Iranian control of the Strait of Hormuz is unacceptable, but the rest of the world is moving on: Iran and Oman are apparently discussing new “fees” they intend to extract from tankers transiting the strait and, per Kagan, several nations that import oil through the channel are negotiating with the Iranians to allow safe passage for their fleets. As Tehran cements its control over global oil commerce, nations large and small will be forced to make nice with its leadership; sanctions on the regime will inevitably be lifted, and further Israeli attempts to dislodge it will be angrily opposed.

 

If a deal to end the war causes a rift between the U.S. and Israel, the Jewish state might come out of this with no friends left at all.

 

The president might answer all that by claiming that he’s trying to end the war because America can’t afford to let it continue—and, for once, he might be right. It’s not just a matter of oil shocks causing economic pain for Americans and political pain for him, either.

 

It’s that he’s overextended himself militarily.

 

Yesterday the Washington Post reported that “the U.S. military has depleted much of its inventory of advanced missile-defense interceptors after expending far more high-end munitions defending Israel amid hostilities with Iran than Israeli forces used themselves.” That problem will get worse if the war resumes, allegedly, because some of Israel’s interceptor batteries are currently down for maintenance. America would need to pick up the slack until they’re back online.

 

The U.S. had already spent down its supply of all sorts of air munitions in this war, as noted here recently, and that deficit will take defense manufacturers “years” to erase. Not only has that affected our ability to fight on effectively against Iran, it’s affecting our ability to deter China: The acting secretary of the Navy, Hung Cao, told senators Thursday that the Pentagon is pausing arms sales to Taiwan “to make sure we have the munitions we need for [Operation] Epic Fury.” That could be a lie manufactured to conceal some sort of corrupt bargain with Beijing—but given how worried America’s allies in the Far East have been about the U.S. diverting assets to the Middle East to battle the Iranians, it could also be the painful truth.

 

The president overextended the armed forces by starting a war that he assumed would be a cakewalk and for which he had no contingency plan if it wasn’t. He’s at risk of overextending them further by starting a new war with Cuba before peace with Tehran has been nailed down. We’re on the brink of another battle royal. And don’t look now, but Greenland also might be about to rejoin the fray.

 

Why does Trump do it?

 

The great man.

 

I don’t think there’s any mystery to it. Almost the opposite: When, throughout history, have megalomaniacs trusted with immense power not eagerly bitten off more than they can chew?

 

Last month, citing those in a position to know, The Atlantic alleged that Trump was no longer comparing himself to George Washington and Abraham Lincoln in private conversation as often as he used to. Being one of America’s greatest presidents has become too modest for his ambition, it turns out; he’s begun to view himself as a world-historical figure in the mold of Napoleon, Julius Caesar, and Alexander the Great.

 

All of whom were emperors and whose word was law, coincidentally.

 

“He’s been talking recently about how he is the most powerful person to ever live,” a source told the magazine. “He wants to be remembered as the one who did things that other people couldn’t do, because of his sheer power and force of will.” His deputies and allies in Congress might worry about where that leads, “but for Trump, the costs have been outweighed by what he views as the opportunity before him, a chance to transform the world in a manner that few historical figures have ever even approached.”

 

He’s in an “I don’t give a f—” mood, another source explained to The Atlantic for the piece, titled “The YOLO Presidency.” Which sounds familiar.

 

Isn’t that what all of this hyperextension boils down to? The president’s hubris about his own alleged invincibility is so overweening that not even hard experience has been able to contain it. Anger at home and abroad over his trade war failed to put him off using tariffs as coercive leverage to settle petty grudges. Thin congressional majorities and terrible midterm polling failed to deter him from declaring jihad on GOP Senate incumbents and saddling them with grotesque excesses like the ballroom and the slush fund.

 

When you regard yourself as the most powerful person to ever live, when you imagine the only obstacle to getting your way is your own restraint in insisting upon it, the idea of being “overextended” must be unfathomable. You won’t learn your lesson about it because you literally can’t.

 

That’s how we ended up in this Strait of Hormuz mess, not surprisingly. Despite being warned that Iran was no Venezuela, “Trump believed that the U.S. military was unstoppable, and that he had a chance to topple Tehran’s theocracy, a prize that had eluded his predecessors,” another piece in The Atlantic recently recounted. “He was redrawing the world’s maps and expected a victory to come in days, a week or two at most.” He didn’t need a strategy, or so he thought. He had dominance instead.

 

I won’t insult the intelligence of learned Dispatch subscribers by explaining why it’s dangerous that the United States is led by someone with messianic delusions of grandeur, who believes there’s no prize he can’t have if he’s ruthless enough about claiming it. But I will say this, to return to a point I made at the start: For probably the first time in its history, this country is now under the authority of someone whose interests are completely divorced from the interests of the people he ostensibly serves.

 

That’s not to say those interests don’t overlap. They do in some cases: The president wants to limit illegal immigration at the border, for instance, and so do most of his constituents. When I say that they’re divorced, what I mean is that how Trump governs is no longer being influenced in any meaningful way by what Americans want. From petty matters like the ballroom and the slush fund to grand initiatives like attacking Iran and subjugating Cuba, everything he’s doing—and will do going forward—is aimed at enhancing his own sense of historical stature, not accomplishing popular priorities.

 

The United States is still nominally a democracy in the sense that it continues to hold elections. (I think.) But insofar as democracy is a mechanism to ensure that elected representatives strive to implement the will of their constituents, it no longer is. The most powerful official in the country could not make it any clearer, especially after this week, that he’s using his power to serve his own interests, not Americans’. If that means that the United States ends up overextended in all sorts of ruinous ways as he chases his dreams, that’s your problem, not his.

 

It was always going to end this way. Nothing was clearer when the president ran again for office in 2024 that his second term would fundamentally be about him, not about “making America great” or whatever jingo right-wingers are using now to reconcile themselves to fascism. He was candid about it on the trail, too: The name of the game in Trump 2.0 would be “retribution,” he warned us, and he’s kept his word. The abiding horror of his second term is that the con he pulled during his first about being a “public servant” was completely exposed by how that term ended—and Americans reelected him anyway. They opted for a president whom they had every reason to know would put his interests above their own, always. They chose overextension.

 

And so, while I hate to end two newsletters in a row on the same point about what Americans deserve, sometimes it can’t be avoided. Enjoy the billions of dollars in new debt we’re about to be saddled with to fund Cuba’s transformation into some sort of Trumpist Riviera for rich Floridians. I know I will.