'Cocksure boor' Trump's disastrous gamble predicted in long-forgotten memoir

Foreign leaders seeking to cope with Donald Trump should not shower the U.S. president with flattery and gold gifts, a former British defense secretary said: they should read a near-forgotten 1991 book that describes Trump as a “cocksure boor who pays precious little attention to detail” and a “a lad who literally grew too big for his britches.”

“You only have to meet people, do the job, read the room to realize that sucking up to Donald Trump, giving him gold watches from Switzerland, doesn't work,” said Sir Ben Wallace, British defense secretary from 2019 to 2023, referring to a common tactic among world leaders regarding the U.S. president.

“There's an amazing book called Trumped! written in 1991 by one of his casino bosses from Atlantic City. It's one of the best reads you can read, because it's not written [as] a sort of kiss-and-tell, ‘I knew the president.’

“… And in there, right in the middle of it, is Trump's obsession with wearing a suit, for example. It goes way back, right? If we'd had good quality advice to people like Zelensky, we would have known that those are the sort of things that touch [Trump] off.”

Speaking on the One Decision podcast, which he co-hosts, Wallace was referring to an incident in February last year when Ukrainian president Volodymyr Zelensky was harangued in the Oval Office by Trump and Vice President JD Vance, in part for not wearing a suit as he sought continued U.S. aid against Russian invaders.

A year on, the U.K. is among countries attempting to cope with Trump in the aftermath of a U.S. raid on Caracas that resulted in the seizure and removal of Venezuelan President Nicolás Maduro and his wife, and amid Trump’s renewed threats to forcibly take Greenland, which is governed by Denmark, another NATO member.

Trumped! The Inside Story of the Real Donald Trump — His Cunning Rise and Spectacular Fall, by John R. O’Donnell, was published in 1991, when Trump was a New York property magnate subject to high-profile business reverses.

Few then predicted a Trump presidency, let alone a concerted attempt to wreck the post-war international order.

O’Donnell’s portrait is not flattering, revealing now familiar character traits including germaphobia, crudity, racism and cheapness.

One contemporary review described an “evenhanded, knowledgeable account” of “a decidedly dull boy whose life story could as easily have been subtitled ‘The Banality of Narcissism.’”

Kirkus continued: “Trump emerges as a cocksure boor who pays precious little attention to detail and pins the blame for his own misjudgments on subordinates. While he seems surprisingly dumb when it comes to weighing a deal's downside risks against its potential rewards, he apparently suffers from near-terminal overconfidence.”

Wallace’s podcast conversation touched on similar themes.

Speaking to Wallace and co-host Kate McCann, a reporter, Philip Gordon, once national security adviser to former vice president Kamala Harris, said he had “sympathy for the dilemmas of the European situation.

“They are dependent on the United States. They're worried about Trump retribution. They're pleading with him to try to stand with them on Ukraine because they fear that without the United States, they're really vulnerable to Russia and not strong enough.

“They're divided. You have some countries willing and ready to really criticize the United States for violating international law and others not. So I understand it and I get it. But the bottom line is, yes, Europe looks irrelevant in this situation. Collectively, I think this has been a trend in the first year of Trump foreign policy.

“Europeans trying to preserve support from the United States through flattery and nice words for Trump and hoping that if they're nice to him and they don't offend him, he'll support them. And each time he just responds to that, again, with contempt.”

Gordon also discussed working for President Barack Obama, who he said “was often accused of thinking things through too much.

“We [thought] about Syria and he would be, second-order effect, third-order, fourth. And … in high levels of government, you can be paralyzed if you worry about everything that could happen because lots of things can happen and you have to be sometimes decisive and take risks.

“But if Obama was guilty of thinking a little bit too much about second-, third- and fourth-order effects, Trump is guilty of not seeming to think about them at all.

“And I think that's what this is in Venezuela. Even when he first started saying, ‘Maduro has to go, we're putting an armada in place,’ I don't think he … was inclined to intervene. And then Maduro pissed him off by dancing and rejecting him and making fun of him and he decided to do it. I think that's where we are now too. But that's the big risk: they don't have a good answer to what next if Plan A doesn't work.”

On Capitol Hill on Wednesday, Democratic senators told Raw Story they feared such an outcome in Venezuela, for now still led by the Maduro regime, if without its figurehead.

According to Gordon, Trump’s Plan A “is to hope that, Okay, they got Maduro, maybe his cronies will be so afraid of the next wave of intervention that they'll do a deal and they'll pay back U.S. oil majors for money they owe them, they'll give them opportunities to invest in Venezuela, and they'll, as Trump says, do what he says.

“So that's the best-case scenario, but the worst case and arguably even more likely case is that they don't … you have the security services, the corrupt ministers of defense and interior, the gangs, the Cubans, the Russians, the Chinese, and they will have every interest in not doing that.

“And I don't think Trump has an answer to that question … Because, we're not there. When Trump says we're running Venezuela, we're not because we're not there. It's all just based on the hope that the fear of Donald Trump will lead them to do our bidding. That's just really risky.

“… If Plan A doesn't work, I don't think he knows what Plan B is. And if Plan B is to have to use force and actually go into Venezuela and do this ourselves, then we run into the same sorts of post-regime challenges that we've seen in places like Afghanistan and Iraq and Libya, and it usually doesn't go well for the United States.”