For more insight and commentary from Michael Wolff, subscribe to HOWL on Substack and gain access to exclusive daily content.
We’re in the middle of a major war on the orders and under the direction of someone whose goals, motivations, and point of view nobody can discern.
Trump may or may not be flying blind, but certainly the world is.
All of the many textbook reasons for war—historical, military, political, economic, defensive or aggressive—are less than relevant because he has only limited awareness of them. What any world leader, ally, enemy, diplomatic expert, pundit, or political pro thinks about war is absent—because it’s Trump. Sometimes he even seems to have an amount of self-awareness about this strange vacuum, proudly proclaiming that nobody knows what he’s going to do because he doesn’t know what he’s going to do, which gives him quite an advantage over everybody else. Beware the crazy man.
This goes, of course, to an even broader breakdown in all the assumptions about leadership and the world order: the most consequential person in the world is, for all practical purposes, a dummy. He neither operates within accepted rules nor with any understanding that he might be breaking those rules, because he’s unfamiliar with them, doesn’t have the language to even address them, and, most of all, truly, just doesn’t give a sh-t about them.
Hence, when he does try to offer an explanation, it’s incoherent, uncaring, contradictory.
The world has simply never faced this kind of situation. All the mandarins, bureaucrats, and consultants in it, who have made their careers on greater and greater spreadsheets of complexity, are face-to-face with a practical primitive.
Because there is no real way to think about an absence of thought, nobody is capable of accepting it. So, everybody defaults to the belief that Trump must have a plan, a view, or a wish—we just don’t know it. He can’t express it or communicate it. But it must be there, mustn’t it?
Marco Rubio must know it.
Judging by the panic on his face, I’d say pretty likely not. J.D. Vance? Jesus, there’s a whipsawed fellow. Keir Starmer? He seems like he’s about to have a public breakdown. Bibi is like, whatever, but hurry and do it before he changes his.
The person I might trust most of all to know what’s actually going on here, and how to manage it, is Jared Kushner, the son-in-law.
He’s the guy, in my experience, with the most clear-eyed view, both opportunistic and resigned, of his father-in-law. He is now, more than anyone inside the government, Trump’s go-to-guy and de facto chief foreign policy advisor.
Jared was the guy to whom Trump farmed out most of the details, deal-making, and general foreign-policy mindshare—all things that bore the president—during the first administration. It was Kushner’s invitation that made MBS, the Crown Prince of Saudi Arabia, Trump’s first foreign visitor to the White House. After that, Persian Gulf wealth became a consistent focus. The UAE, Qatar, and Saudi Arabia, were the crescent of opportunity. And while Trump was personally pissed off that his son-in-law snagged a $2 billion payoff from the Saudi’s without him benefiting, it also fortified his acumen in Trump’s eyes.
As his personal representatives, rather than government officials, Kushner and Trump’s golf and investment buddy, Steve Witkoff, now control the Middle East. “It’s their portfolio,” Trump says. That might sound like a diplomatic portfolio, but it’s as much a “financial portfolio.”
“Jared can really work the Arabs. They like Jews to handle the money,” he adds with great satisfaction, likely unaware of his head-smacking antisemitism.
Of all the mixed, unclear, incoherent, and incomprehensible motivations Trump might have in the Middle East, and in the war with Iran, one clear and basic goal always does exist—his own personal advantage. The country should benefit from his actions, yes, but why shouldn’t he benefit too? This isn’t grift; this is fairness. He’s not working for free.
Always, the best way to understand Trump is to focus on what’s in it for him. In any endeavor, however misguided and seemingly inexplicable, there will be an eye-on-the prize calculation of how he personally can come out ahead.
His world, random, disorganized, undisciplined, mercurial, make-it-up-as-you-go-along, has, over decades, always had a consistent focus on his piece of the pie.
The presidency has not changed his way of thinking. As he wages war, oil, real estate, partnerships, Persian Gulf capital, and deal-making will be top of mind.
Trump doesn’t know how to fight a war, and he certainly can’t seem to justify one, but with his son-in-law as his bagman, he’ll figure out how to profit from one.
