Michael Wolff On Trump's Psyche

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.