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Failing Up

My family's secret to success
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TRIGGER WARNING: This video contains a pathological sense of entitlement and egregiously terrible a cappella singing. Only listen if you're feeling impervious to the aforementioned or you’re already tone deaf. [sorry]

It’s very hard to believe, but apparently there are still a lot of people out there who think that 1) Donald is enormously wealthy and, 2) he created that wealth himself. In 2018, however, thanks to Sue Craig and Russ Buettner, investigative reporters for The New York Times, it was revealed that during my grandfather’s lifetime, Donald received $413 million in trust funds, gifts and unpaid loans. After my grandfather died, Donald inherited a couple of hundred million dollars more. It bears pointing out that the empire Donald has manage to squander over the last thirty years—the one he is in danger of losing thanks to his having committed massive fraud (allegedly)—belonged to his father. It was never his.

My grandfather, Fred, had long harbored aspirations to expand his real estate business across the river into Manhattan, the Holy Grail of New York City real estate, but he didn’t have the right skill-set. Donald, on the other hand, did possess the kind of brazenness and total lack of self-awareness that allowed him to bulldoze the rest of the world into believing he was some kind of entrepreneurial phenom.

He wasn’t—even Fred knew he wasn’t. Still, Donald dedicated a significant amount of time crafting an image for himself among the Manhattan elite whose circles he was desperate to join. Fred understood Donald’s limitations and knew he was promoting a fiction, but he didn’t care. He wanted the fame—and he was perfectly happy to live vicariously through Donald’s. Fred was paying for it, after all.

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Donald, on the other hand, always believed the fiction to be the truth. He believed it with such force that tens of millions of other people now believe it, too. We see how that’s played out—is, in fact, still playing out.


Most people in my family also suffer from the obnoxious belief that they’re better than everybody simply by virtue of the fact that they have a lot of money, despite not having earned it. With the exception my dad, none Fred’s children was self-made, either. Even Maryanne got her federal judgeship through Roy Cohn who agreed to do Donald a favor. Unfortunately, our society’s obsession with fame, wealth, and power help people like Donald, his siblings, and his children get away failing up, which seems to be their only legitimate skill.

I’ve often said that narcissism and arrogance make people stupid (just look at Jared’s portfolio when he worked in the White House as a senior advisor). It can also make them behave with an extraordinary sense of entitlement. Eric’s wife, Lara—who only a couple of years ago, toyed with idea of a senate run in North Carolina, the point having been proven by her father-in-law that qualifications are irrelevant—apparently feels she’s within her rights to steal Tom Petty’s “Won’t Back Down.” Donald already received a cease-and-desist letter from Tom Petty’s estate for playing it at one of his rallies. Now, Lara refers to it as “my song” simply because she recorded some auto-tuned version. It’s disappeared from the Apple playlists, she claims, not because she stole it but because it’s being “shadow-banned.”

It's a minor point but, as we keep learning, small transgressions add up. Unaccomplished grifter sons become media celebrities who somehow end up sharing nuclear secrets with wealthy foreign nationals who paid for the privilege in the form of a country club fee. We may never find out what those secrets were. We may never know how much or what kind of damage was done by revealing them. What we do know is that Donald justifies his treason by claiming he had every right to the documents and, therefore, had every right to do whatever he wanted with them.

He's been indicted for the crime of stealing highly classified government documents, yes, but he’s suffered no real consequences. His rubes continue to throw money at him which he uses to pay his legal bills, and he’s still running for president.

When it comes to his impunity, so far no one has proven he does not possess it.

But the charges, the scrutiny, the testimony in six different jurisdictions are starting to take a toll. Donald can lie and spin as much as he wants in the hallways and on the steps of the court house. None of that will fly, however, in the courtroom in front of a judge who has all of the power and is more than happy to remind Donald that he has none.

He showed up in New York voluntarily because he knew how important this fraud trial is not only to his reputation but to the core of his own beliefs about who he is. He left because he knew nothing he did—the pouting, the angry stares, the media hits—was working. That plus the humiliation of falling off the Forbes 400 were too much for him to take. With any luck, it’s going to keep getting worse for him.


Tomorrow I’m launching a new feature for paid subscribers called “Deep Dives.” In the very first interview I’m going to break down the history of Donald’s manipulation of the media in reporting on his “wealth” with Jonathan Greenberg, the man who was (literally) conned into putting Donald on the Forbes 400 way back in the 1980s. Please upgrade to watch.

Let's go!

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Mary L Trump