Too Much and Never Enough

Despite my terminally poor performance [at playing the board game Monopoly, as a youngster], I never once changed my strategy; I bought every Atlantic City property I landed on and put houses and hotels on my properties even when I had no chance of recouping my investment. I doubled and tripled down no matter how badly I was losing. It was a great joke between me and my friends that I, the granddaughter and niece of real estate tycoons, was terrible at real estate. It turned out that Donald and I had something in common after all.

Since my father’s death, Donald has suggested that ‘they’ (meaning he and my grandfather) should have ‘let’ Freddy [the author’s father] do what he loved and excelled at (flying) rather than force him to do something he hated and was bad at (real estate). But there’s no evidence to suggest that my father lacked the skills to run Trump Management, just as there is none to suggest that Donald had them.

Nothing is ever enough. This is far beyond garden-variety narcissism; Donald is not simply weak, his ego is a fragile thing that must be bolstered every moment because he knows deep down that he is nothing of what he claims to be. He knows he has never been loved. So he must draw you in if he can by getting you to assent to even the most seemingly insignificant thing: ‘Isn’t this plane great?’ ‘Yes, Donald, this plane is great.’ It would be rude to begrudge him that small concession. Then he makes his vulnerabilities and insecurities your responsibility: you must assuage them, you must take care of him. Failing to do so leaves a vacuum that is unbearable for him to withstand for long. If you’re someone who cares about his approval, you’ll say anything to retain it. He has suffered mightily, and if you aren’t doing all you can to alleviate that suffering, you should suffer, too.