Trump’s Iran headaches are mounting

The Iran war hasn’t gone well for President Donald Trump since, well, shortly after it began.

Despite extensive US military attacks and economic pressure, Iran hasn’t felt the need to capitulate to Trump’s demands. And even when there have been ceasefires with favorable terms for Iran, Tehran still didn’t abide by them.

But Trump’s headaches with the war are mounting. And many of them extend beyond the battlefield and the negotiating table.

Some of the recent developments:

And through it all, Iran only appears to be growing bolder and upping its demands — perhaps believing that its leverage is increasing.

All of the above threatens Trump’s ability to keep prosecuting the war. And these developments add to the costs of a war — now in its sixth month — whose purpose Americans have never been convinced of in the first place. The president insists he’s not feeling the time pressure, but some in his party would beg to differ with the midterms looming.

The plane switch in particular threatens to add a layer of scandal over the already unpopular war. And as much as anything, it undercuts the administration’s claims to have decimated Iran militarily.

This week we learned that the Trump administration feared a threat from Iran was serious enough that it warranted sneaking the president off Air Force One for his departure from Turkey last month. (CNN reported Wednesday that the threat involved a shoulder-fired missile.)

The munitions supply has long been a sleeping giant. CNN has reported that Joint Chiefs of Staff Chairman Gen. Dan Caine and other military leaders warned Trump before the war began that the stockpiles could be an issue in a protracted conflict.

Trump seemed to anticipate a much shorter war, lasting four to six weeks or so. But that’s not what he’s gotten. And increasing reports, including from CNN, suggest Caine’s warnings were well-founded and that key munitions are significantly depleted. The US military has exhausted nearly 80% of its interceptors for a key missile defense system, known as THAAD.

The Trump administration has claimed it has plenty of munitions to finish the job in Iran. But that doesn’t address whether the war might cause the US to be so short of critical munitions — which take time to replenish — that it leaves the country exposed or might embolden an adversary like China to try and invade Taiwan.

That’s increasingly a cost-benefit analysis that administration officials will need to consider. But it’s already a dynamic that threatens Trump’s ability to apply pressure on Iran.

A major question, of course, is whether military or administration officials could even prevail upon Trump if they regard the munitions issue as being dire. But there are increasing signs that key figures are growing weary of the war and sending signals that it might be time to ramp it up.

CNN reported last week that Caine has privately made clear to other top Trump advisers that the administration needs to find an off-ramp from the war because the military options on the table to escalate the conflict could backfire, and airpower alone is unlikely to achieve Trump’s objectives.

There are also signs that loyal Trump allies are increasingly concerned about the war costing Republicans in the 2026 midterm elections. House Speaker Mike Johnson said recently that “we’ve got to wrap it up,” and Fox News host Laura Ingraham has said the “clock is ticking.” (Indeed, the Guardian recently reported that more Iran war skepticism is seeping in on the normally rah-rah airwaves of Fox.) Even cheerleaders for Trump and his war effort like right-wing influencer Benny Johnson have signaled it’s time to move on.

“Foreign wars with no end in sight are always unpopular. They will always be political cancer,” Johnson posted on X two weeks ago. He added: “End the war. Be done. Refocus on America. Gas, grocery, home prices and immigration. Thats how we win.”

The length of the war also appears to be contributing to another problem for the administration’s ability to keep prosecuting it: fatigue, poor living conditions and declining mental health among the service members tasked with supporting the war effort.

News outlets Stars and Stripes and the Navy Times have reported multiple attempts by crew members aboard the USS Abraham Lincoln to jump overboard. A sailor recently went overboard, CNN reported, before being rescued.

And around 200 family members of Lincoln crew members voiced concerns about the situation — including lack of supplies, food shortages and water contamination — at town halls last week in San Diego. The Lincoln has been deployed since November and hasn’t made a port call in more than 200 days, which Democratic Sen. Richard Blumenthal of Connecticut said is a modern-day record for consecutive days at sea.

The US Navy said it takes “every service member’s well-being seriously and have religious, medical and mental health professionals available to assess and address concerns as they arise.”

But the emerging story epitomizes Trump’s problems.

He seems to regard continuing the war and keeping up the economic pressure on Iran as largely a cost-free endeavor. The US doesn’t have boots on the ground and there aren’t constant stories about troop deaths. Rising gas prices have been the war’s biggest political problem.

But as the situation stretches months beyond when the administration signaled it would end, other problems are seeping in. Some of them make continuing the war more difficult on a practical level, while others suggest the stalemate will keep giving the administration political problems that it — and its allies — have to reckon with.

And given the war was already looking like an albatross and a quagmire – with the midterms less than three months away — these are pretty inauspicious developments.