Why Can’t Donald Trump Laugh?

The president’s niece diagnoses her family’s dysfunction.

President Donald Trump appears to look at himself in a mirror.
President Donald Trump at the White House on Wednesday. Brendan Smialowski/Getty Images

On Thursday’s episode of Trumpcast, Virginia Heffernan spoke with Mary Trump, daughter of President Donald Trump’s older brother Fred Trump Jr., holder of a Ph.D. in clinical psychology, and author of the new book Too Much and Never Enough: How My Family Created the World’s Most Dangerous Man. This partial transcript of their conversation has been edited and condensed for clarity.

Virginia Heffernan: How witting is Donald Trump in his worst fraud? What do you think, based on what you know about him?

Mary Trump: I think in the context of this question, the most important thing to know about Donald is that he’ll accept help of any kind if it benefits him. This is a man who knows the difference between right and wrong, but he doesn’t think it applies to him if he can get help that’s going to advance a cause of his.

In my family, it was kind of an unwritten rule that certain behaviors that would have been crossing a line for other people were OK if you were a particular Trump. Not all of us, obviously, but if you were a particular Trump.

How does that get conveyed to you?

Through watching, especially watching how my grandfather treated my dad. Donald learned very early on. My dad was seven and a half years older, so Donald had the benefit, if you want to call it that, of watching his older brother be abused and criticized and humiliated. But he also had the benefit of seeing how my dad was kind and generous and how much his friends loved him. So the message Donald got was don’t be like Freddy. Be a killer, be tough.

All the kids—well, I don’t know about the girls in the family, but all the boys—worked in my grandfather’s office in the summers and maybe on weekends once in a while, so they saw how he operated. They saw how he treated people. They saw the kinds of people he rubbed elbows with. He was very connected to not just the Democratic machine, which was very influential in Brooklyn back in the ’40s and ’50s, but mob figures and other unsavory creatures.

I think of Felix Sater giving your cousin Ivanka the tour of the Kremlin, letting her sit in Putin’s chair. You bring your kids along to meet the most important people you know!

That’s right.

Sometimes on this show, I’ve wondered, can Donald Trump do anything? He can’t toss paper towels in a normal way or go down a ramp. We know that. But you also make it clear he can’t do business. I mean, can he throw a baseball? Is there some rubber-hits-the-road moment where he displays a talent? The hole at his center seems to be that he’s almost absolutely without merit.

When we were kids, he did throw the baseball around with us. Way too hard, quite honestly. I doubt he could do that anymore. But I agree with you that somebody of such privilege, who had all of the opportunities at his disposal in the world, is so limited in scope in every way, in terms of intellectual curiosity, in terms of interests, in terms of skills. One of the things that was important for me to convey was the concept of his having been institutionalized, essentially.

I find this fascinating. With your training, you can probably recognize the hallmarks of institutionalization, and yet it’s weird to think of Donald Trump as being like someone who grew up in an orphanage. Walk me through that. Is military school when it first starts, or is it just being born into the Trump empire?

Certainly by the time he was a teenager. He’s never wanted for anything, he’s never had to make a living. He never has made a living. He went from my grandparents’ house to the very regimented military school, back to the house, to my grandfather’s company, to the Trump Organization, which I view as a sinecure for him.

And then The Apprentice, whatever that was, and the White House. The Apprentice isn’t a place, but it was an environment that perpetuated the same things. Everything was taken care of, nobody said no, you were protected from your own failures, and you were allowed to succeed despite those failures.

Your father took great pleasure in life. I keep thinking of this prank where he had a friend hijack a hearse and one of them gets in a coffin. It’s exactly the kind of thing you can’t imagine Donald doing. There’s something so humorless and sterile about him. Is he happy?

There’s no way he could be happy because the myths that have been created about him and that he’s perpetuated and believes about himself are always in constant danger of disintegrating. On some deep level, he knows that. He’s very much always living in the moment. So how can you be happy?

And how can you be happy if you don’t laugh or appreciate humor? What that says to me, because my grandfather also didn’t laugh, is that laughing is to make yourself vulnerable, it’s to let down your guard in some way, it’s to lose a little bit of control. And that can’t happen. That is not allowed to happen. So, no, I don’t believe he’s happy. Unfortunately, I don’t believe he’s capable of being happy, because it wasn’t something to aspire to in my family.

I found your book unspeakably bleak. The thing that brought me to serotonin zero was your observation that the Trumps’ signature dish is iceberg lettuce and mashed potatoes. Tell me about the aesthetic of the family.

I think it stemmed, first of all, from the fact that my grandmother was from this tiny village on a tiny island off the northwest coast of Scotland, and she was an awful cook. We had rice out of a box, which is fine, but she still couldn’t cook it properly. And Russian dressing, hysterically enough, was a really big thing. It was the Russian dressing that’s basically mayonnaise, ketchup, and relish mixed together. Part of it is that my grandfather didn’t really care. He was a man of very basic appetites.

So it’s not really surprising that people in that family would grow up to be feeling starved. And that’s what’s so weird. Even with all of that money, not Donald, but certainly Maryanne and my dad, they were starved of everything.*

What’s the deal with sexuality in the Trump men? It’s similar to the starvation around the mashed potatoes. No imagination, no sense of romance, nothing human about it.

We can look at a lot of things this way in the context of this family. There’s something—an activity or a need that all human beings share, but for them, the actual human element of the need or the activity is completely elided. So the thing that makes it actually worth having doesn’t exist for them.

With women—and my grandfather had a bit of a reputation, too—it’s the objectification of them as objects to be taken, controlled. It’s not so much about the physical pleasure as it is about the control or the getting away with something.

But then it’s also this weird way that he has of reducing women to their parts. He can’t see them as fully whole human beings. How can you engage in any substantive interesting, romantic, loving way with somebody if that’s the only perspective from which you experience them?

To hear the full interview with Mary Trump, subscribe to Trumpcast in Apple Podcasts or listen below.

Correction, July 23, 2020: This article originally misspelled Maryanne Trump Barry’s first name.