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Why this Iran comment from Trump’s top general is a big deal.

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In the lead-up to his State of the Union address, President Donald Trump has been hitting more roadblocks than he’s used to.

Last week the usually pliant Supreme Court ruled that his emergency tariffs are illegal. Around the same time, we have since learned, his top general warned him that attacking Iran would be fraught with huge risks. Meanwhile, polls show his ratings have tanked to an all-time low, with 60 percent of the country dissatisfied with his performance, leaving some Republican lawmakers skittish about locking their own fates so firmly to his.

The military warning—first reported in the Washington Post, then confirmed in the New York Times—must be particularly rankling. According to the reports, in a recent White House meeting with many top officials present, Gen. Dan Caine—whom Trump selected, and has since highly lauded, as chair of the Joint Chiefs of Staff—said that a shortage of munitions and the absence of any allies would make a prolonged war with Iran very difficult. (In previous conflicts with Iran, some Gulf allies in the region have actively assisted; this time, they say they won’t even allow U.S. or Israeli planes or missiles to fly over their territory.)

It is unusual for Trump’s advisers to dampen his fantasies of easy wins, and it is less common still for high-level discussions of military plans to be leaked. The fact that Caine confronted Trump on this plan, and that someone spilled this to the public, suggests a growing concern among some inside players that the president’s increasingly casual adventurism could engulf the armed forces, the region, and the nation in danger.

Trump disputed the Post’s account on social media, saying Caine “has not spoken of not doing Iran,” but this is what reporters used to call a “nondenial denial.” The news reports didn’t claim that the general had opposed an attack, but rather that he laid out the challenges of proceeding with one. Trump also said Caine told him a military action would be “easily won”— a highly dubious claim. First, Caine is known to be cautious in his appraisals. Second, almost no military leader would deem a war of this sort “easily won”—especially given memories of the catastrophic quagmire in Iraq, a country one-third the size of Iran with a less entrenched regime.

In his social media message, Trump noted Caine’s successful attack last June on Iran’s three main enriched-uranium sites. However, Operation Midnight Hammer, as the attack was known, was a speedy one-off venture where three B-2 bombers dropped bunker-busting bombs, watched them hit their targets, and sped back home, the end. Trump may also be emboldened by the lightning-fast attack on Venezuela to nab the country’s dictator, Nicolás Maduro.

A larger attack on Iran—whether to wipe out more of its nuclear infrastructure, destroy its ballistic-missile fleet, or overthrow the regime—would be a much more elaborate, time-consuming business. Trump has mobilized two aircraft carriers, 16 additional warships, dozens of fighter aircraft, and an array of air-defense weapons to shoot down missiles that Iran might fire in retaliation. Even so, Caine has told him the amassed firepower may not be enough to complete the task, whatever the task might be.

Trump must be confounded by the resistance and the warnings, which are new things in his otherwise rollicking second term as president. So many people and institutions have caved in to his pressure tactics: Members of Congress have surrendered their constitutional powers; media executives have punished or canceled critical commentators; universities have shut down departments and altered admissions policies; foreign leaders, fearful of losing still-essential U.S. security guarantees, have kissed his ring and praised his sagacity.

Wait, Is Trump About to Go to War With Iran?

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Perhaps Trump figured it would be equally easy to bring the mullahs of Tehran to their knees. Steve Witkoff, Trump’s former fellow real-estate tycoon, now his chief emissary to crises around the world, suggested as much in an interview on Fox News over the weekend. Witkoff said Trump was “curious” as to why Iran hadn’t “capitulated” to the looming threat of an American attack. “Why,” Witkoff wondered, “under this pressure, with the amount of sea power and naval power over there, why haven’t they come to us and said, ‘We profess we don’t want a weapon, so here’s what we’re prepared to do’? And yet, it’s sort of hard to get them to that place.”

Of all the remarks that Witkoff has uttered over the past year signifying his unsuitability for the job he’s been inexplicably handed, this one might take the proverbial cake. Why haven’t the Iranians surrendered before a shot is fired? Maybe because: A) Trump has offered them no serious way out of the crisis (the negotiation positions that Witkoff and Trump’s son-in-law, Jared Kushner, have put on the table would be unacceptable to any head of state), B) he’s left American military personnel and allies in the region vulnerable to a retaliatory attack, and C) he’s explicitly threatened to bring down Iran’s regime, so retaliation would likely be extreme, as there would be no reward for restraint.

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    Why This Iran Comment From Trump’s Top General Is a Big Deal

Sometimes Trump’s top aides give him good advice, but he doesn’t take it. CIA Director John Ratcliffe has told him that Russian President Vladimir Putin’s war aims are to wipe out Ukraine as a sovereign nation. Trump should have inferred from this that peace negotiations with Putin are a waste of time, but talks persist and Trump sides with Putin more often than not.

Now the chairman of the JCS has given him military advice on Iran that should prompt Trump to rethink his whole approach, but he seems unmoved here as well, still seeking an easy solution to a crisis that he is far from the first president to face.

International politics is hard. Coercive diplomacy is harder still, especially if you haven’t thought through your diplomatic goals, haven’t tried to scope out the interests or incentives of the leaders you’re trying to coerce, and have now been told by your top military adviser that your tools of coercion might not be up to the task.

Trump still has a moment to shift course—on all the points of resistance that he’s met this past week: on tariffs, his wider policy agenda, and the perilous calculations of war and peace. But his playbook has no chapters on admitting mistakes or rethinking options. The consequences, for all of us, may soon be all too apparent.

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