Trump's unlikely comeback: Michael Wolff chronicles the chaos of a political resurgence

Journalist Michael Wolff has been chronicling the extraordinary trajectory of one Nathan Detroit-esque, sails-close-to-the-edge, property developer Donald Trump, the man who, now, quite improbably, is America’s twice-elected president. Wolff’s previous writing on Trump (as well as on Rupert Murdoch) demonstrated the author’s swagger, tied to a sense of all-knowing omniscience and wicked humour (writing that generated criticisms aimed at him such as, “How could he possibly have known that!”). 

With his latest volume, All or Nothing: How Trump recaptured America, Wolff’s book pretty much does merit the all-too-frequent hyperbole of being “unputdownable”. 

This volume follows Trump’s exiled semigration to his Mar-a-Lago club in West Palm Beach, Florida, after his defeat in the 2020 election, despite the defeated president’s denial of this reality. There are in-depth timelines of events about Trump’s tribulations on multiple, overlapping judicial agonies that presumably heralded his presumed political demise, along with details about his never-ending electronic snarls about how the deep state, Joe Biden, the media, and so many other enemies had all tried to bury him and how he would get even — improbably.

Read more: The difficulty of analysing Trump as a transformative force in global power and governance systems

Wolff delivers eye-opening detail about how Trump staged his extraordinary return to power, aided by conspiracy-touting social media outlets and stumbles by then President Biden, as well as Trump’s belief that the various criminal and civil trials would, in the end, help feed the legend of an invincible leader. Trump almost immediately saw that the Butler, Pennsylvania, assassination attempt — and the iconic photo of him framed by a national flag, blood on his head —  would redound to his near-legendary status. As it did.

Along the way, Wolff offers vivid portraits of some usually low visibility, just below the radar aides such as Natalie Harp (the young woman who carried a portable printer with her everywhere in order to chum Trump with tidbits of deep rightwing conspiracy writing).  

And then there is the somewhat mysterious Boris Epshteyn who fed Trump’s massive ego and his taste for conspiratorial thinking as well as an improbable sense that all would be well, and who was significantly responsible for shaping the Trumpian legal strategies in defeating — or at least blunting — most of the trials.

Read more: As Trump sows chaos, electoral realignment could be coming to US politics 

Epshteyn generates the realisation among the campaign and with the candidate that the campaign and the trials were one and the same, and that they and the resulting media reporting, in turn, was virtually interchangeable. In all this, Trump and his coterie — and his MAGA followers — saw him as a man of fortune and destiny.

Or, as Ross Douthat, the conservative columnist for the New York Times (and yes there are some there) observed of Donald Trump, fate, fortune, and destiny, the other day, “…the idea of a man of destiny, a great man of history, is a useful way of thinking about that when it happens, as I think it has happened with Donald Trump, the rise of populism, the crackup of the liberal order and so on… it’s important to stress that someone can be a man of destiny and be bad. Someone can be a great man of history and be worth opposing. You can look back at Napoleon and say: man, he was above and beyond, in terms of historical forces — and also root for the Duke of Wellington at Waterloo.

“It is very hard to go through the kind of drama that Trump himself personally went through in the world that ran from Jan. 6 through his return to power — and, if you’re on his side through that story, not come away with a feeling that you were sort of moving with the wave of history. For people in Trump’s circle, there’s just a sense that it doesn’t matter what the polls say or the naysayers say. It certainly doesn’t matter what squishy New York Times conservatives say. They saw the bottom: Trump was disgraced and ruined and persecuted, and he was going to be sent to jail. And then the next thing you know, assassin’s bullets were missing him by a hair’s breadth. And he was making this incredible, unprecedented historical comeback.” (We have never seen Donald Trump on horseback, but maybe that trope is no longer needed if one is a man of destiny.)

Unfortunately for the rest of us, Trump’s resurrection has had little to do with the actual implementation of real policies, something increasingly apparent as his support among Americans at his first hundred days has fallen to the lowest level for a newly inaugurated president over many decades. This has been noted by every single polling outfit — save, perhaps, for the one inside Donald Trump’s head. But this sense of destiny, coupled with policy incoherence, does not bode well for the nation. 

Read more: Trump after 100 days — America First president is overturning the world order

Economic historian Brad DeLong, observing the chaos of trade and tariff policy in the Trump administration, wrote for his Substack blog earlier this week: “The lies (being told by the administration) are in the service of an attempt to cover up what everyone knows is the truth: the Trump administration is structurally incapable of negotiating anything. Nobody has the baton. Trump has no ability to focus or evaluate.

“Congress has not and will not give Trump trade promotion authority — the power to tie an entire deal up into a single package and submit it to congress for an up-or-down vote.

“Trump claims to have already negotiated ‘200 deals’. (Treasury Secretary Scott) Bessent says he is talking about sub-components of ongoing negotiations. But nothing is agreed to, ever, until everything is agreed to: whatever these are, these are at best proposals, not ‘deals’. And they are almost surely not even that — there is no staff to write them down, and nobody has been told what the Trump administration wants, other than ‘something big’. Why not? Because the Trump administration has no desires or plan — just grievances and irritations…”

But to true Trumpians probably none of this matters very much, or at least not nearly so much as salving those Trumpian grievances. Or, as Wolff wrote in his own summation: “He will reach out to punish enemies, and because of his threats, some knees will surely bend before him. But then he will make more enemies, which will distract him from his original targets… Certainly he will be guaranteed an unending supply of obsequious foursomes (in golf). Chaos and audacity will continue to be his friends, because that combination keeps him at the centre of attention — his real enjoyment — and, as well, distracts from problems that might actually require his attention. And he will focus as he always has on his real life mission — on his own PR and how to put himself on Mount Rushmore. But there is, too, the inescapable fact of his age, term limits, second term malaise, and his lame duck status — power ebbs. At some point, as hard as it might seem to imagine, events will have a life of their own without Donald Trump at the centre of them. And then the story will end. Meanwhile, amid the disorder, and perhaps in place of what surely seems to be his consistent inability to find peace and satisfaction, Natalie will be just outside the Oval Office door writing letters to him.”

Given the vividness of Wolff’s descriptions of meetings and conversations among many in Trump’s circle, one has to hope that somewhere, in some safe deposit box, wrapped in plain brown paper inside a nondescript shoebox, there is a fully annotated copy of the book's manuscript, replete with footnotes detailing the sources for all this material. Historians will want to have a look at it for sure, the moment Donald Trump truly passes from the American political scene and on into a fulminating retirement laced with a growing senescence. DM

All or Nothing: How Trump recaptured America, Michael Wolff, 2025, Bridge Street Press/Little, Brown Book Group.

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