Michael Wolff On Trump’s Psyche

We unpack the president’s unique pathology.

Michael is a media critic and author. He’s been a columnist for New York magazine, Vanity Fair, British GQ, the Hollywood Reporter, and the Guardian. Among his many books include four on Donald Trump — the third one we covered on the Dishcast, and the latest was All or Nothing: How Trump Recaptured America. He also co-hosts the podcast “Inside Trump’s Head.”

For two clips of our convo — on Trump’s closest lackeys, and examples of the best resistance to Trump — head to our YouTube page.

Other topics: lawfare as central to spurring Trump to run again; his epic comeback after losing in 2020; retribution; Michael’s dinner with Donald and Melania; the near assassination and “Fight!”; 14 years as a reality TV star; his brilliant campaign stop at McDonald’s; how he met Epstein; their obsession with young models; Karoline Leavitt morphing into a model; the cold arrangement of his marriage to Melania; Ghislaine Maxwell; Bill Clinton; how Trump treats female aides; Lindsey Halligan and the Comey indictment; Susie Wiles; Trump’s surprising pick of Vance; his reluctant choice of Pence; Jared Kushner; Stephen Miller and targeting judges; Don Jr and crypto corruption; Musk’s fundraising; January 6; McConnell’s chance to remove Trump; Trump’s strange deference to Netanyahu; the MAGA fissures over Israel and Epstein; the Mossad conspiracy over Kirk; Tucker 2028; Hegseth’s speech to the generals; sending troops into US cities; Trump’s visit with King Charles; Jerome Powell’s backbone; the law firms, universities, and news outlets that caved; Mamdani; the legendary luck of Trump; and what he might do if Dems take back the House.

Browse the Dishcast archive for an episode you might enjoy. Coming up: Charles Murray on finding religion, Karen Hao on AI, Michel Paradis on Eisenhower, David Ignatius on the Trump effect globally, Mark Halperin on the domestic front, and Arthur Brooks on the science of happiness. As always, please send any guest recs, dissents, and other comments to dish@andrewsullivan.com.

On the recent episode with Wesley Yang:

Thanks for publishing my dissent last week, and I want to comment briefly on your brief reply. You stated that the transgender movement is no longer a civil rights movement, since trans people were covered under the 1964 Civil Rights Act in Bostock. I completely disagree, and I’m somewhat surprised you would say this. Even after civil rights are recognized, there remains further litigation and other battles to determine what these rights mean under the law, how they’re applied. If simple recognition under the law were enough, civil rights would be a closed subject for all protected classes, not just the transgendered.

I also note, as an aside, that Republicans in Congress and in some states have introduced bills that would eliminate or at least restrict trans civil rights, and opposing these efforts is part of a civil rights movement.

You also stated that the trans movement is now a cultural revolution. I agree. I simply want to point out that all civil rights movements are also an attempt at cultural revolution. Legal recognition of rights is a prelude to cultural acceptance; the two are inevitably connected. Another way to look at it: if cultural acceptance for a group was already the norm, it would be frivolous to pursue legal civil rights.

On your first point, yes, there will be lawsuits and actions that flesh out those rights. But the core battle is over. Trans people have full civil rights in a society which is as friendly to them as any in human history. This narrative of “oppression” mocks the actually oppressed.

And there is a difference between cultural acceptance and cultural revolution. Same-sex marriage is an example of the former, where including gay men and lesbians into an existing institution both empowered them and reinforced broader social norms. The replacement of the sex binary with gender is the latter: it uproots the entire society, removing the distinctions between men and women that are integral to reality, and assaults gay rights as well as women’s rights. I oppose it first, as a lie, and second, as a power grab.

Here’s a dissent from a trans reader:

I transitioned almost 25 years ago, including medically and legally — obtaining a court order even! I was hired as a female for a faculty job by my present employer (a large public university in the Midwest) about 15 years ago. Despite a stellar record and never a single complaint, in the past few months I have been banned from using the women’s restroom at my university because of changes in Ohio law (see HB 183, HB 96). I am functionally barred from most events because there are few single-user restrooms on campus.

The response from the state and writers like you, of course, is to use the men’s restroom, because of biology. Well whatever, but while we are talking about plumbing, check mine. I could not physically use half the facilities in a men’s restroom if you paid me to do so.

What you, the MAGA conservatives, and frankly annoying trans activists have done over the past several years is erase transsexuals like me from the discussion. All of you lump all trans women together without seeing the fact that there are real physical differences between people based on their surgical status. A minority of trans women have a surgically constructed vagina. Sure, it may be fake, but it’s more real than the imaginary penis that many on the right imagine I have.

The conservatives say that I and people like me are a threat … with what? I have no more threatening equipment than any other woman of my pretty modest size. Frankly, I look pretty unremarkable naked, but I would sure stand out in a men’s restroom or locker room. And frankly, I’d probably arrested if I stripped in a men’s locker room and booked on a sex charge until I could get someone to bring all the paperwork to the jail.

There was no rational basis to keep me out of a women’s restroom for nearly 25 years — and that was the way society mostly treated people like me until about five minutes ago. It’s why a humane state like Utah made an exception to their bathroom legislation that recognized people who had undergone sex-reassignment surgery (HB 257). It’s why the original bathroom bill, North Carolina’s HB 2, did as well. But sadly, this is not where we are going.

The reality is that all trans people are not the same, and increasingly those who have undergone sex reassignment really are being hard done by many of the very recent changes in public policy nationwide. Your arguments on trans people as a group are often like the fun house mirror of a transgender activist over the past dozen years. You lack nuance.

Point taken. I have tried to make distinctions between actual transexuals and the gender woo-woo crowd, but obviously not enough. I’m grateful for the upbraid. And that policy is dumb. I have long opposed restroom bans as de trop, and only consider full-nudity locker rooms to be problem. But the distinction between post-op transexuals and the dude who just decided he feels like a woman today is huge and important. I guess what I’m saying here is: I’m with you. And I think the genderqueers have hurt legit transexuals by their postmodern hooey.

From a fan of last week’s episode with Katie:

While I love to find time to dissent every now and again, I instead want to send a full-throated, ringing, exuberant, emphatic assent in response to the pod with Katie Herzog. What an important episode. Thanks, and take care!

More praise for the episode:

I have been reading and listening to you for a few decades now, and there are days when I want to scream at you — such as when you characterized Kamala Harris as “one of one dumbest Democrats alive.” But that’s definitely part of your charm. If you don’t occasionally infuriate your readers, you aren’t Andrew Sullivan …

But tonight, as I was listening the last morsels of your conversation with Katie Herzog, I realized that one of the things I love about the Dishcast is your ability to create a sense of warmth and even intimacy with your guests, and to bring us into that intimacy. (I LOVED the birds and fish and environment tangent you chased towards the end.) You also manage to make subjects I have no interest in fun and interesting and engaging, as was the case with Katie.

Here’s a dissent from a “long-time member of Alcoholics Anonymous”:

OMG, I finished that episode very disappointed. You never allowed Katie to go in depth about what her experience was with the Sinclair treatment and the end result. I listened to the entire pod and still don’t know how this is working for her. You kept veering off into the weeds on a multitude of topics, ending with a lengthy digression about climate affects on the environment. All of those topics were of interest to me, but not at the expense of the topic at hand.

Then the two of you categorized heavy drinkers as alcoholics. This is very misleading to someone who might not know better and may be struggling with alcoholism. To say that alcoholics can just put down the drink when a struggle is resolved, or when they got out of college or some such thing, is absolutely false. There are millions of alcoholics who know this isn’t true and spend decades trying to summon the willpower to do so. Someone with alcoholism has what is medically termed as an allergy to alcohol, which sets off a craving that only another drink will satisfy. There are “problem drinkers” who better fall into the description you and Katie included in the “alcoholic” category, and that is dangerous information to put into an alcoholic’s mind.

Also, saying that AA has a stranglehold on the courts is a complete and total misrepresentation. Judges and courts require AA because it has been proven, for the last 90 years, to work. If you had looked into the subject of AA before you interviewed her, you would have been aware of AA’s traditions — particularly tradition 11, which states that our public relations policy is based on attraction rather than promotion. AA does not go around petitioning courts to send their drunks to AA, which is what was inferred in that interview.

As a long-time member of AA, I speak from direct experience. Yes, getting sober was initially hard, but I would not opt to take a pill when I wanted to drink that would rob me of the joys in life I have found through AA. I mean, what is the point of her taking a pill that removes the effects of alcohol? That is one of the questions I was hoping would have gotten answered. And what does she get out of drinking if she doesn’t get the “high”?

Today, after 16 years in AA, I can tell you that it isn’t the slog that she inferred it was. Maybe for her it was, because she never really had a desire to stop drinking. AA’s 12 steps bring us back to the source of all that is good, which is so often called God. With our spirituality restored and continually maintained and growing, we live lives beyond our wildest dreams. And we learn how to “live life on life’s terms,” which many of us never learned how to do.

Please don’t think that I am saying AA is the only way to find sobriety. I imagine there are some other options, but at 70 years old and decades of trying ANYTHING BUT AA, I have found it is the only lasting solution — to say nothing of the benefits of the entire psychic change that occurs through the 12 steps.

Well, it seems as if I have pulled “an Andrew” and digressed — though I did not forget to complete the topic at hand. Thank you for your consideration. I am truly a big fan of yours.

Happy to air that perspective and sorry to disappoint. But you might find this email illuminating:

Whether you realize it or not, you’ve done a tremendous service for your listeners via the episode with Katie Herzog. Yes, I agree with you that she’s one of our funniest commentators, and the discussion was a delight. More importantly, though, having had a similar experience to hers, I’m convinced that raising awareness of naltrexone and the Sinclair method could help thousands, if not millions, of people.

As she suggested, the ranks of the ignorant include far too many doctors. I was fortunate to stumble upon an anonymous Substack post about the Sinclair Method just as I was recognizing the scope of my own obsession. Despite overcoming the shame of popping a pill to solve my problems, I still had a hard time getting started. Though my physician had rightly scolded me several times for drinking so much, when I later proposed naltrexone as a solution via an electronic consultation, she seemed skeptical and instead asked me to come in to discuss it face to face — which meant waiting six months for an appointment. Hardly the prompt response I wanted to my health epiphany.

Fortunately, there are a number of services online that offer online consultations and prescriptions.

In addition to reading Katie’s book, readers may find it helpful to know that if their normal doctor is unreceptive, there are small companies issuing legitimate prescriptions online. Some are a bit more bare bones and focused on expediency, like webdoctors.com (one I can personally vouch for), and others supposedly are coupled with a bit more emotional support and programming at a slightly higher cost, like Oar Health. Some of these are obvious side hustles for the doctors, but the options are out there — and they work for a lot of people.

I can’t recall either of you using this oft-cliché term in the episode, but the alcohol obsession I couldn’t shake was truly Pavlovian. I had become little more than one of his laboratory dogs, salivating in front of my liquor shelf, brainwashed by my own neurotransmitters. Once a drinking habit has given the brain an expectation of dopamine, the brain will push you until it gets what it wants. As I understand it, it’s one of the reasons that some people who quit drinking begin to consume a lot of sugar; it’s another way for the brain to get its dopamine rush.

It took all of two days using the Sinclair Method to notice the difference. (Though, as Katie mentioned, there are other ways to use the drug, and readers may find this old NYT article helpful, as well as a story PBS NewsHour did on naltrexone.)

Of course, it takes considerably longer than two days to truly re-train one’s brain. But once it happens, the changes are radical: I’ve lost weight, I have a thousand times more energy, I spend less money, my mind is sharper, and I sleep more restfully. In an AA-centric environment, some people find this bizarre, but I am one of the people Katie mentioned who still drink. I’ve long been a wine enthusiast and collector (I hate using that word, but alas, it’s apt), and I’ve regained the ability to have one glass and stop. Unfathomable before naltrexone.

Having now gone through this, and knowing my own mental discipline in other areas of my life, it’s sometimes disheartening to hear cynics who claim alcoholism and addiction are just a matter of willpower, and to know friends who think AA is the only viable path. I’ll spare you the Sam Harris-ish conversation to be had around the idea of free will and the commonplace Cartesian understanding of mind and body as distinct entities. But for many people struggling with alcohol, they’re really struggling with their own dopamine, which hijacks whatever sense of willpower one has. Thus a little pill that keeps one’s cerebral reward center in check gives one an opportunity to break the habit with staggering effectiveness. I’d never felt so useless as when I realized I couldn’t stop myself, so the regained sense of will, be it real or an illusion, is most welcome.

So I’ll reiterate: by having Katie on the Dishcast, you’ve no doubt offered some of your readers a transformative opportunity. I hope anyone who recognized themselves in her comments will dig deeper. Thanks, as always, for the great programming.

You’re welcome. By total coincidence, I had dinner planned with a friend here the night before the podcast. When I noted how fresh he looked, how clear his face was, he told me his drinking problem had been solved by Naltrexone. I was so relieved. Such a lovely man, such a debilitating problem. We need to talk more about Naltrexone. It should be as well known as Ozempic.

On last week’s column, a reader writes:

I’ve been thinking a lot over the past week about your piece on how the left lost its way, and it brought to mind many conversations I’ve had with friends over recent months. I’ve been a Labour member for many years, but I’ve grown increasingly concerned about the lack of seriousness when facing the scale of the problem before us and the reluctance to ask how we got here.

Many of my friends in the party maintain a sort of terminal incredulity about the forces now facing us and their possible root causes. They acknowledge Starmer’s uselessness. Yet so many believe that all we need is someone who will make the positive case for immigration. They refuse to entertain the possibility that the consensus on this issue — such as there ever was one — might be collapsing around them.

“There’s just a strain of xenophobia in the country,” they say. “Why else would people protest outside hotels used to house migrants?” (This, after one such hotel at the centre of protests was found to have housed an illegal migrant now convicted of assaulting a young girl.) “London is a diverse city; people should get over it.”

Even those trying to do some good seem to miss the bigger point. A friend, a sitting MP, can write earnestly about the need for “developing a notion of Britishness” without seriously questioning how a country that has existed for centuries should suddenly find itself grappling with such existential questions. It strikes me as a tacit admission of failure — a failure of the redefinition of Britain, post-1997 in particular, which many took for granted.

I’ll stop now before I start rambling for too long. It’s only that I’ve felt increasingly lonely politically — lonelier than during the nonsense of the Corbyn era. My family are Labour people. They came from the slums of London and, over generations, built a new life for themselves. These people loved their country deeply and never lost a sense that the Labour movement was where their hearts and loyalties belonged. It’s painful to watch that cause dissolve into a haze of fantasy and wishful thinking. I can’t shake the feeling that something darker might be hurtling towards us, and I wish people treated it with the seriousness they claim to hold.

Me too. Another reader dissents:

As always, you deliver your central premise with aplomb, but I hope you don’t mind me pointing out a couple of crucial elements I’ve seen missing in this, and your other posts-from-afar about the UK.

First point: London is not alone as a majority non-white megacity. NYC is 70% non-white and Paris 49%. At its height, ancient Rome had 45% non-citizens and slaves — both groups typically not “white.” Fact is, megacities are built on immigration, and the most successful are open — but they trigger the negatives you mentioned. Why aren’t we talking about Silicon Valley’s two-thirds of tech workers being foreign-born? We’re okay with Satya Nadella and Sundar Pichai, native-born Indians, because they are CEOs of the two mega-est corps?

Point is, economic success in today’s world comes with cultural debt — especially for smaller countries that don’t have the population manpower of China and India. Post-war London and beyond accepted people from former British colonies to help in the establishment and restoration of critical public good services, such as the NHS, urban infrastructure, and retail markets.

Second point: When will the people who voted Brexit take accountability? As you say, it’s not on Starmer, but on the people who voted Brexit and will likely vote Reform. But let’s not kid ourselves: anyone who voted Brexit knew perfectly well that the white EU migrant population would dwindle or cease; it’s now negative. Anyone living in London remembers that Pret (a famous sandwich shop) used to be full of dynamic young Spaniards, Italians, Poles, and Romanians. They were then given marching orders, many racially abused, and most have left, with Pret now staffed by majority non-EU migrants.

The same goes for countless pubs, cafés, and hotels. After Brexit, we all knew there would be a low-skill and key-worker job shortage that British people would not fill. It doesn’t take a genius to figure that out, but unfortunately, the only genius on hand was Boris. Remember his “I LOVE ASIA” fanboy tour?

I don’t remember much complaining from OG Brexit hawks like Farage and Gove. What was their answer to the skills shortage? Right: they didn’t have one. So Boris laid the red carpet for a few select countries (mostly Commonwealth nations such as India, Nigeria, Hong Kong, and Pakistan) that already had legacy UK visa pathways, and their immigration requirements are by no means easy. Remember that 70% of non-EU migrants in 2024 are students or workers passing stringent admission tests — the students filling the hole that EU students left. They now shoulder our universities for the UK’s social benefit.

So, I query your answer of letting students come, pay their way, create formidable future-of-work minds … and then make them leave. What a waste of investment and human potential for the UK. If the re-visa idea adds equitable scrutiny, fine, but beware of it becoming a US-style deportation squad (which I’m not saying you are advocating) that may not be able to delineate a key worker and send valuable people home.

Brexit was our first self-hamstringing, leaving us one leg after we got rid of the Europeans. We must be careful not to fall for the same trick and hamstring our only good leg by getting rid of the world.

Then what’s left? Yes, likely a more white UK — perhaps a renewed sense of identity and Englishness — and I see the value for people like your family and that old lady witnessing such rapid change. But they will be left in a country where she can’t see a doctor, find a carer, or visit a local Sainsburys past 3 p.m. on a Wednesday.

Britain is a wonderful nation with a rich history, but it is fast losing its lustre and becoming a tier-2 economy. That’s nothing to do with migrants; it’s due to incapable politics, economic dysfunction, and an aging white population. I worry that the kind of country pictured will be like an old man whose family never visits and whose care worker, Ibrahim, has left. Britain’s “Great” came from Empire — and like it or not, you build empires on the backs of others. You can’t have one without the other.

All good points. The best is the stark reality of native population decline. Even Reform makes an exception for foreign care workers and the NHS: an army of non-whites to help white people die. But even Reform’s plans would only remove up to 600,000 of the four million admitted in just four years. So the question really is about pace and scale and the capacity of a country not to lose its own sense of self and continuity. I worry the pace and scale have been far too much.

Shifting to the American side of my column, a reader quotes me:

[Ta-Nehisi] Coates’ sole evidence [that Charlie Kirk used slurs and was a hater] is that Kirk said “tranny” twice in 752 pod episodes over six years, a word that was ubiquitous among gay men until ten minutes ago.

Agreed. I remember the old “Trannyshack“ in San Francisco’s South of Market District. It was years ago, but it wasn’t 100 years ago:

I also remember when Dan Savage got raked over the coals for using the word — though of course it was deployed with affection. I miss a gay world where outrageous speech was more common than safe spaces.

Here’s a “proud Bernie convert”:

You wrote:

We’re not stupid. No amount of fake rhetorical moves to the center will work. When very basic things that most human beings take for granted — that foreigners are not citizens and citizens come first, that men are not women, that children are not adults — are deemed fundamentally immoral in one political party, that party deserves to lose.

I don’t think you’re stupid, but associating Ezra and Keir and Joe Biden with a left-wing vision for the UK or USA is a mistake. The most frustrating thing I’ve seen in the last 10 years from the Democratic Party (which I finally left in 2021) is its performative leftism with policy measures that are mostly materially centrist. They’ve ignored the class issues that have caused every part of the party to flee in droves and then pretend they’re an “ally” on national television to scoop up as much money as possible. They’re the party of gay rights but decide behind closed doors that one of their leading stars is a VP nonstarter because he’s gay.

Real left movements should be focused on class, wealth taxes, rebuilding the social contract, and nothing else. No more kneeling in the capital veranda. Give up woke? It’s all they have left! Embarrassing.

Another disaffected voter also quotes me:

“Disagree if you want, but why is this ‘fundamentally and morally wrong’?” The answer is because if it’s not — if such beliefs are permissible — then the woke have no moral leg to stand on. Wokeness is predicated on the sincere belief among the Elect that they are better than you; they are more moral than you, more virtuous than you, on “the right side of history,” and you’re destined for the trash heap — just like Bull Connor and his ilk. It is the most smarmy, smug thing I have seen in my 58 years. Woke = narcissism.

So to elevate you — who holds more moderate, sensible views — is to lower them. It lowers their stature, lessens their ability to set the terms of debate, calls into question the moral certainties they insist we all must accept, period. No matter what the election outcomes, their view are obviously morally correct, based as it is in “empathy,” or so they’d claim.

They’re the secular equivalent of the loudmouth “fundagelical” Christians during the George W. Bush administration — utterly convinced of their own rectitude. And it’s that attitude — not the actual policies, but the attitude — that has caused millions just like me, a former lefty, to swear off liberalism and tell these people: Fuck off and get over yourselves.

I can’t stand them either. This final reader isn’t helping us sleep at night:

Regarding the midterms, I’m telling you that we’re all suffering from a complete lack of imagination. Trump will declare an emergency — and will not recognize any Dem victories. He’ll pull out all the stops, and I wonder if anything will be able to impede him.

He’s definitely trying to provoke a response. Think of the 250th anniversary coming up next year. He’s planning celebrations in every state. If there are counterdemonstrations, which there surely will be, he’ll declare those protesters unAmerican and crack down hard. He’s going to invoke the Insurrection Act; it’s just a question of when.

Everyone I tell this to invariably says that I am catastrophizing. But Trump benefits from no one actually believing that he’s going to do all this crazy shit — which he always ends up doing, eventually. From all of the people I talk to in this administration, and within MAGA world generally (and I know some prominent individuals), I honestly do NOT believe that these folks are ever planning on relinquishing power. I can hear Trump himself now, saying he is “standing in the breach, and could not possibly let these ‘evil’ Dems take any reins of power.”

And sorry, I just believe the whole “Dems will do it when they take over” argument really no longer carries much weight. Chief Justice Robert’s immunity decision last summer was a huge mistake — the direct ramifications of which we will soon see, I fear.

I would certainly appreciate any feedback; I always appreciate your analysis. And as always, thank you for your attention to this crisis.

I totally understand where you’re coming from. The combination of terror and farce in this administration is bewildering. Vigilance always. We have more than three years to go.

Thanks for all the dissents and other emails, and feel free to send yours to dish@andrewsullivan.com.

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