Michael Wolff: How Trump Digests the News
Making novelist sense of the child that runs our lives
“There was things which he stretched, but mainly he told the truth.”
—Mark Twain writing about Mark Twain (in Huckleberry Finn)
I’m coming to appreciate Michael Wolff, the avid Trump chronicler, who is also, for a number of reasons, sometimes discounted. He’s had a long career as this biography shows, much of it with big players in East Coast media (New York Times, New York magazine, Vanity Fair). He’s also published books, starting as early as the ‘70s through today.
I say this to say I find Wolff’s work fascinating, especially in these times. He often focuses on the sensational and the splashy, so his work gets attention. It’s also, for the same reason, often criticized — witness Wolff’s recent claim that Andrew Lownie’s book Entitled said Jeffrey Epstein had sex with Melania Trump before his friend Donald did and in fact introduced the two, claims that the publisher of the book to which Wolff referred, under possible threat of lawsuit by Melania herself, has since removed as “unverified.” The outcome of all this a threatened suit against Wolff, with Wolff suing Melania in response. Whew.
In addition to events like the Melania story above — who knows what’s the truth in that case? — Wolff has often been accused, sometimes plausibly, of getting facts wrong in his own work and writing fictional scenes. Consider this review of Wolff’s book Burn Rate, for example, from 1998, in which many of the book’s claims are disputed. (Wolff defended this work as accurate.)
You get the idea. Does Wolff stretch? Perhaps he does. Maybe it’s likely he does.
Yet to my novelist’s eye, he gets at the truth. There’s something right in his claims — however he comes to them — that makes me say, Yeah, I get it. This now makes sense.
The Question of Trump’s Ideas
For example, consider the question of Trump. Why does Trump say what he does? How does he arrive at his obvious improbable lies? I used to think they came to him on the spot, his thoughts and words, as a kind of instant, audience-inspired opportunism. Does saying this work? Let me try it. That sort of thing.
Yet we’re also told the man just doesn’t think, that he’s easily bored, that he’s dumb. His former Secretary of State called him an “fucking moron” — I believe he meant “moron” literally — and his former Defense Secretary said Trump had a grade school mind (those quotes are here).
So does Trump have a feral intelligence? Or is he dim in the head? If the last, what’s the source of his ramblings?
Wolff’s Trump: Fiction or Fact?
All that said, I offer this explanation of how Trump arrives at “the facts,” how he processes news, from reporter Michael Wolff (from the preview of a paid post at Wolff’s new Substack site).
Trump is usually up early and watching the three screens in his bedroom (three screens continues to reflect that his heart is in a network television age). He’ll have watched Fox & Friends, CNN, sometimes Joe and Mika [Morning Joe], and maybe a bit of the Today Show. Then his first call will be with one of his comms people—often Stephen Cheung—and he’ll ask for a recap of what he’s just watched. The basic approach is that bad news needs to be reinterpreted as good news. If it absolutely can’t be presented as good than [sic] the bad news has to be cast as the product of a nefarious and conspiratorial left-wing world. Fox will have already laid down this script—not least of all because Fox is in constant communication with the Trump staffers who know what the script needs to be.
Trump staffers are proud of their ability to deliver the Trump world view. So proud, that on more than a few occasions I’ve heard them display this studied skill on the speaker phone, Trump prompting them and fishing for what he wants them to say, them delivering it (they do this, showing off, with a certain studied nonchalance). The ability to interpret the world as he wants to see it—“How’s it playing?” he’ll ask—is the key skill set that gives a staffer the primacy with the boss that they all seek.
Mamdani landslide and this new Muslim figure in American politics would sunder the Democrats and that his radical left-wing socialism would be a red-hot threat to Trump voters everywhere (and, in Trump’s mind, would win back the Jews for him—a very sore spot that they haven’t long since flocked to his side—“I can get the spics and not the Jews, what the fuck?”). The bad news that could not be rejigged as good news was the victory, also a landslide, for Gavin Newsom’s redistricting in California plan. But here, obviously, was a diabolical conspiracy: a stolen election. DOJ investigators would be put on alert.
See what I mean? It makes sense.
A man wakes up, maniacally searches the news for what involves him — which is just about everything now — then maniacally seeks from his staff how to digest all that in a way that makes him look good, or at least makes his foes look bad. When he gets what he wants, stories that make him feel good — it’s all about feelings, it seems — he stores their spin and later, repeats what he heard, happy to show that he’s right.
Like a bird open-mouthed in the nest and waiting for food, selected and predigested so its primitive gut can absorb the nourishing goo, Trump waits to be fed, even seeks to be fed, what others have masticated. Now, that explanation makes sense; it comports with what we observe. It sounds really right.
Folks may think Trump is great, transformative, just what we need, the best that’s come down the stairs since God set that hick Andrew Jackson loose in DC. Be that as it may, as a story of how the man works, Wolff’s story makes perfect sense, makes a kind of novelist sense, makes sense of the character stuck in our mind’s TV.
Is Wolff’s story verifiable? God only knows. Wolff doesn’t name sources, often the case with him. But for me, it’s still valuable, with that provision, that it may have the truth of fiction, which not none at all.
More Michael Wolff
For this reason, I’m going to start featuring Michael Wolff more. Not because he dots all his I’s, but because his claims, unverified though they be, make novelist sense of the man that has come, like a child-colossus, to stand over all of our lives. It’s good when the world makes sense.
I have also taken to listening to the Daily Beast/Michael Wolff YouTube show “Inside Trump’s Head,” since it’s become too expensive for me to subscribe to all of these paid Substacks.
The most interesting thing that Wolff has disclosed is what Jeffrey Epstein allegedly told him about the Maison de l’Amité property sale in Palm Beach that precipitated Trump and Epstein’s falling out. Epstein claimed to Wolff that Trump bought the property out from under him in in 2004 for $41M via a deal put together by Wilbur Ross using Trump as a front for money that out of favor Russian oligarch Dmitry Rybolovlev was hiding from his wife, via a phony “loan” from Deutsche Bank. Epstein told Wolff that he got mad and threatened to go to the feds with the money-laundering allegations, but that Trump “snitched” his teen-pimping operation to the feds instead, destroying his credibility.
Trump subsequently “sold” the property to Rybolovlev for $96M and the property was subdivided into three lots and sold by Rybolovlev at “wash” prices lampooned in the local press as a “bad” deal. However it was only a “bad” deal if the $96M wasn’t a sham transaction that might let Rybolovlev avoid a gain and that Trump might have been able to offset with his casino losses. So you can very likely add tax evasion to money laundering. It’s how they finally got Al Capone.
Wolff describes all this in his books “Siege” and “Too Famous” — Wolff now writes that when “Seige” came out in 2019 Epstein called him from Paris, worried that he had over-shared. Epstein was arrested upon his arrival in Teterboro and died under suspicious circumstances a short time later.
Whatever one thinks of Michael Wolff as a writer, most of the underlying facts and timing of the Maison de l’Amité deal can be independently corroborated. I agree that he’s worth listening to.
This seems right to me. I've long thought he was utterly reliant on staffers to create the world he wants to live in.
Aside from the public facing people, Leavitt and Cheung, we don't seem to know the names of the masticators. That would be a great place for activism.