Lucky Loser

alex4th June 2025 at 1:22pm

[the notes from the book were retrieved with kobogarden, with the purpose of aiding to create a map of the ideas the book left me. The full list of book highlights can be found here.]

American politics is (now?) equal parts fascinating, exhausting, and even a bit fun, albeit only in the sort of devillish, grotesque kind.

Frequently it feels like there is a big mismatch between any kind of action and the purported rationale that supports it. There's the impression that decisions are taken with little regard to its consequences, and very often with very unclear goals, and/or dubious motivations. And this is not something one would expect from leaders of the world, or people (once) portrayed as being hallmarks for good decision making.

What I mean is: it really does feel like Donald Trump is, in many ways, just (unfortunately?) fundamentally stupid (poor fella!), operating at a much basic and irrational level than what the media and adjacent institutions believe — or make believe. Of course, I can understand why it might be of best interest for all to assume (or pretend) a base of rationality — otherwise, the public admission of institutions being hostage to immature and deranged decision making might do more harm than good. In any case, the preceding paragraph, as the world stands today, would probably be big enough of a liability for me to consider travelling to the United States. If only I were somebody, of course.

Well — this book, of course, arguably confirms that most damning perspective, as it follows the trajectory of the father through the period of Donald taking over (and why did Fred believe his son was so, so smart?). Being, fundamentally, a piece of journalism, it provides previously hidden context on the true finances (and thus, the real history) of Donald Trump (little Donnie!).

The resulting story, published in October 2018, revealed for the first time that Donald Trump had received the equivalent of more than $400 million from his father, much of it through fraudulent tax evasion schemes. The story disproved Donald Trump’s lifelong claim that his father gave him nothing more than a “small” $1 million loan. For our work exposing the true state of Trump’s finances, we were honored with a Pulitzer Prize.

I've been reading it on and off, because very often this feels like a pointless exercise — almost a waste of time — or a gratuitious foray in dabbling with the absurd. It frequently occurs to me that a book like this, in these times — it mostly feels like fiction. There are absurd amounts of wealth, a lot of fraud and opportunism (Fred Trump, father to the current President of the United States, really did build a fortune over tax evasion and fraud) and an ultimate detachment from values one would arguably consider baseline for humans in general. So that part is a bit sad.

The doctor induced labor [for Ivanka's first child] on New Year’s Eve, the one-year anniversary of their engagement and not quite nine months after their wedding. She would later say that when she told her husband the boy’s name would be Donald J. Trump Jr., his response was, “What if he’s a loser?” Ivana told him that the name was her decision because she had carried the baby.

Donald’s work associates wondered whether the timing of the induced birth was pure luck or soulless tax planning. He could now claim a dependent tax deduction as if he had been a parent for twelve months when it had been true for only about six hours.

It almost doesn't even matter whether the book actually portrays the truth, or whether these things really happened. It's all so weird, and frequently so spectacularly stupid —

Outrage soon spread among the city’s art and historic preservation circles. The New York Times was notified. Hawkins told a reporter about Donald’s prior promise and expressed his disappointment. “Architectural sculpture of this quality is rare and would have made definite sense in our collections,” he said. Miller described watching the destruction. “It was just tragic. They were very much in the Art Deco style, very beautiful and very gracious.”

A reporter called Trump’s office for a response. Donald chose to hide behind his alter ego, John Baron, who claimed to be a vice president of the Trump Organization and said the company had decided that the “merit of these stones was not great enough to justify the effort to save them.” He said an appraiser had found the sculptures to be “without artistic merit,” a dramatic departure from experts with the Metropolitan.

On the fourth day of news stories expressing shock that Trump had broken his promise, he finally emerged from behind his John Baron shield. Donald was quoted saying he had been out of town, and that this Baron fellow had it wrong. The $32,000 cost of removing the sculptures was not an issue. “I contribute that much every month to painters and artists—that’s nothing,” he said, which appears to have been entirely untrue.

The issue, Donald said, was that the delay would have cost him hundreds of thousands of dollars. But really, he insisted, he was only thinking of everyone except himself. “My biggest concern was the safety of people on the street below,” he told the Times. “If one of those stones had slipped, people would have been killed. To me, it could not have been worth that kind of risk.”

About some tax gymnastics that Donald felt entitled to when trying to build something in New York City,

One reporter wrote that Donald called Tony a name that implied that he would be most at home “having some grain thrown into his pen.”

“This 350-pound commissioner tells me I’m not gonna get my tax abatement,” Donald told the reporter. “I said, ‘You’ve gotta be kidding.’ I’ve given more than I’ve gotten. I’ve given them a hotel, the Grand Hyatt. It was a craphouse five years ago…. I built a beautiful hotel and I have 1,500 people working there.”

He mentioned his efforts to get the city to build the convention center on the land on which he held an option, for which he received a $500,000 commission and framed it as an act of generosity. “They were gonna build the convention center over the water. The piles might go all the way to China before it hit something. Instead, I’ve given them a better location farther downtown and they’ll have a better facility. All I did was save them 150 to 200 million dollars. All of this, and nobody has ever said, ‘Thank you, Donald.’ Instead, they make me look like an idiot.”

I think I will not read further more — at least for the time being. It's not worth it — there are certainly better uses of one's time.

TitleLucky Loser
AuthorRuss Buettner
PublisherPenguin Random House