Michael Kruse is a senior staff writer for Politico.

In 1985, Tony Schwartz, a writer for New York magazine, was sitting in Donald Trump’s office in Trump Tower interviewing him for a story. Trump told him he had agreed to write a book for Random House. “Well, if you’re going to write a book,” Schwartz said, recalling this interaction in a speech he gave last fall at the University of Michigan, “you ought to call it The Art of the Deal.”

“I like that,” Trump said. “Do you want to write it?”


These sorts of arrangements typically are not that generous for the writer. “Most writers for hire receive a flat fee, or a relatively modest percentage of any money the book earns,” Schwartz said in the speech. Schwartz, by contrast, got from Trump an almost unheard-of half of the $500,000 advance from Random House and also half of the royalties. And it didn’t even take a lot of haggling.

“He basically just agreed,” Schwartz told me in an email, meaning Schwartz ever since has brought in millions of dollars more of royalties and Trump has brought in millions of dollars less.

It’s a telling example, Harvard Business School negotiating professor Deepak Malhotra said in a recent interview. “What should have been a great deal on a book about negotiation actually is one of the most interesting pieces of evidence that he’s not a good negotiator.” Malhotra, the author of Negotiating the Impossible, pointed out Schwartz even got his name on the cover, and in same-sized text. “I don’t think there’s a better ghostwriting deal out there.”

The book, of course, became far more than a surprising and lasting commercial success—it also was central to Trump’s appeal as a presidential candidate.

“We need a leader that wrote The Art of the Deal,” he said in the speech in which he announced his candidacy in 2015.

“I’m a negotiator. I’ve done very well over the years through negotiation,” he said in a Republican debate in 2016.

“That’s what I do, is deals,” he said last month. “I know deals, I think, better than anybody knows deals,” he added.

The Friday Cover Sign up for POLITICO Magazine’s email of the week’s best, delivered to your inbox every Friday morning. Email Sign Up By signing up you agree to receive email newsletters or alerts from POLITICO. You can unsubscribe at any time. This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

But these past 16 months of Trump’s presidency have shown that whatever skills Trump thinks he acquired over the course of his business career haven’t necessarily translated to his work in the White House. The failed repeal-and-replace health care negotiations, bungled efforts to get funding from Mexico for his promised border wall, the pulling out of the Trans-Pacific Partnership and the Iran nuclear deal—Trump has proven to be more adept at breaking deals than making deals. And the sudden and bizarre scuttling of his meeting with murderous North Korean dictator Kim Jong Un that had been scheduled for June 12 in Singapore—and now might be back on again—is only the latest data point that suggests he’s either not as good at negotiating as he promised he was, or that negotiating with disparate factions of Congress or in geopolitically fraught international arenas is harder than he thought it would be and harder than anything he’s ever done. The truth, according to negotiation experts who have studied Trump’s track record, people who have negotiated for him and against him, associates, biographers and former employees, is that it’s all of that.

Trump was, and still is, they say, a confident, competitive, aggressive, impulsive, zero-sum, win-at-all-costs, transactional, unpredictable, often underinformed and ill-prepared, gut-following, ego-driven, want-it-and-want-it-now negotiator. His self-burnished image as a tip-top deal-maker long has obscured an actual record that is far more mixed, pocked with moves and acquisitions that scratched a passing itch but created massive financial problems later. His best work, too, was his earliest work. Trump was at his most patient, his most diligent, his most attentive and his most creative—his most effective—some 35 to 45 years ago, when he was intent on pile-driving into the cultural bedrock powerful storylines on which he would build his career as a celebrity business tycoon.

Donald Trump rubs an oversized ‘magic lamp’ during the opening ceremony for his Taj Mahal casino in Atlantic City, April 5, 1990. | AFP/Getty Images

At no point, though, in the past nearly half a century—from the shrewd, well-timed talks that led to the Grand Hyatt and Trump Tower in midtown Manhattan to the agreements behind The Art of the Deal and “The Apprentice”—did Trump’s negotiations in real estate and entertainment circles prepare him fully for the degree of nuance and complexity he now faces as president. And his abrupt cancellation last week of the North Korea summit, in the estimation of the negotiating experts I talked to, was a scramble to reclaim a modicum of the leverage he gave up when he too eagerly consented to the meeting in the first place. But Trump’s decision to leave open the possibility of rescheduling (“… please do not hesitate to call me or write”) as well as the ongoing back-and-forth between his administration and its North Korean counterparts signal that he still wants to meet because he still needs a negotiating win heading into November’s midterms.

“That’s his style,” Jack O’Donnell, a former Trump casino executive who negotiated for him and also watched him negotiate, told me. “He will say anything to keep people thinking that they’re going to wind up doing a deal that’s good for them. He gets people to believe, or tries to get people to believe, that they’re going to get a really good deal—even though he’s obviously only concerned about getting a good deal for himself.”

“He will be safe, he will be happy, his country will be rich,” Trump said a week and a half ago. “Kim will be extremely happy if it works out.”

The problem is that what works in business doesn’t always work sitting across the table from a 30-something dictator who runs modern-day concentration camps and is bristling with nuclear weapons. “When you’re an executive in the private sector and you badly want something, and you can’t control yourself when you really should have, you get hurt,” Harvard’s Malhotra said. “When you behave this way in the public sector … other people get hurt.”

When you’re an executive in the private sector and you badly want something, and you can’t control yourself when you really should have, you get hurt. When you behave this way in the public sector … other people get hurt.” Deepak Malhotra

Negotiation expert Marty Latz has a book due out this month called The Real Trump Deal: An Eye-Opening Look at How He Really Negotiates. “If you take a look at the research as to the actual skills that the most effective negotiators exhibit,” Latz told me, “you’re looking at skills like assertiveness, empathy, creativity, ethicality—how ethical you are—and skill sets like those are not necessarily in the DNA of Donald Trump.”

The bottom line for Latz on Trump: “Is he truly a masterful negotiator? I would say not—in business, and certainly not to date as president.” And all of this, he said, is so important. “In fact,” he writes in his book, “nothing may have a more direct impact on the safety, security and prosperity of the world than Donald Trump’s negotiating skills.”



***

Why do so many people think Trump is such a skilled negotiator?

Because he says so—over and over and over.

Trump leans on a large prop letter “T” in this 1996 photo. | Getty Images

“Some people have an ability to negotiate,” he said in 1984, referring to himself, offering in the Washington Post to represent the United States in negotiations about nuclear weapons with the Soviet Union in the thick of the Cold War. “It’s an art you’re basically born with. You either have it or you don’t.”

At the time he had some reason to preen.

It wasn’t arms control summitry, but the conversion of New York’s decrepit Commodore Hotel to the shimmering Grand Hyatt at Grand Central Station was a triumph. It took years. The barely-30-year-old Trump had to convince agents of the bankrupt Penn Central railroad, lenders, brokers and city and state officials to buy into his plan, and he did it with salesmanship, verve, cunning and good timing. The end result when the hotel opened in 1980 was the most generous tax abatement in New York City history and a launching pad for Trump’s career. “He was clever,” biographer Gwenda Blair told me, “pushing all the pieces around the board.”

Ditto with what he did next—Trump Tower. He saw an opportunity where others didn’t, and he jumped on it, getting the land from a faltering department store and leveraging that to acquire the air rights he needed to do what he wanted to do. He was involved in the project down to the nitty-gritty of dealing with subcontractors.

“We used to get the sub, and we used to sit ‘em down, and we used to say, ‘OK, what’s your best price?’” Barbara Res, the Trump Tower construction manager, told me. “And they would tell us, you know, $5,650,000 or something, and we would say, ‘OK, go in with $5,800,000, and Trump’ll beat you down. Because Trump had to get his pound of flesh. And he had to believe that only he could do that.”

Trump had to get his pound of flesh. And he had to believe that only he could do that.” Barbara Res

But Res often was impressed.

“Damned if Trump wouldn’t get ‘em down to $5,500,000,” she said. “So sometimes he actually did better than we did.”

How?

“No. 1, maybe he was a little smarter than we were with the sub,” she said, shortening “subcontractor.” “No. 2, there was the star factor, you know? We didn’t have that, but Trump did. And No. 3, he was very good at ‘futurizing.’ He called it that. It’s getting somebody and making them believe they have a future with the company and so they should therefore take less money or do more work or whatever. The last thing he said is he would put them on the map—and, you know, Trump Tower did put a lot of subcontractors on the map.”

Trump had the leverage. And he used it. But this level of discipline and focus started to dissipate in the mid-‘80s—starting, ironically, with Schwartz’s The Art of the Deal deal.

It wasn’t the only context, though, in which Trump was devil-may-care with his negotiating around this time. As an owner of a team in the fledgling United States Football League, he overspent on players. (In the aftermath, in fact, of his big-bucks signing of quarterback Doug Flutie, he had the gall to ask other owners to help cover some of the costs. And he did it through his now-infamous faux spokesman. “When a guy goes out and spends more money than a player is worth, he expects to get partial reimbursement from the other owners,” “John Barron” told the United Press International in 1985.) Trump overplayed his hand, too, when he led the league’s lawsuit saying the National Football League was a monopoly. The misguided strategy led to the end of the USFL.

Donald Trump and Herschel Walker shake hands in March 1984 after Walker signed a four-year contract with the USFL’s New Jersey Generals, which Trump owned. | AP

Down in Atlantic City, Trump’s first two casinos had opened in ’84 and ’85, respectively. Boxing was a big part of the show, but Trump left to his deputies lots of the negotiations for fights.

“When we were meeting with Don King and these guys, no, he was never there,” O’Donnell told me. Trump, he said, was consistently hands off. “He’s not the guy that’s sitting down face to face doing the negotiating—he just didn’t do that with the deals we were involved in. I mean, listen, we did have to go to him, but it was more, ‘What are we willing to pay for this?’ ‘Well, we’re willing to pay $12 million … or whatever the number was. And he’d go, ‘Yeah, get it at 12. That would be great.’ But literally that would be a 30-second conversation.”

It was not a rigorous process. “Some of the deals we used to do were, ‘Get it at all costs,’” O’Donnell said. “It was just, ‘Get it.’”

He also on occasion listened to Trump spar with contractors. He came away from the experiences thinking of Trump as a sort of for-show tough guy. “He postured,” O’Donnell said, “and then when he hung up, he was like, ‘So, what did you think of that?’”

There’s one year in particular that looks in retrospect like a concentrated accounting for what happens when Trump wants things too badly and underprepares and overpays.

In 1988, he bought Manhattan’s Plaza Hotel for $407.5 million—almost $60 million more than even a high-end estimate of what the landmark was worth. “How can I live without it?” he said during the negotiation. Even Trump knew it wasn’t prudent. He paid for full-page ads in the New York Times and New York magazine. “I have purchased a masterpiece—the Mona Lisa,” he wrote. “For the first time in my life, I have knowingly made a deal which was not economic—so I can never justify the price … ”

It wasn’t his only bad deal that year. In the negotiations that April in Trump Tower in which Trump gained from Merv Griffin control of the casino that quickly would become the debt-bloated Trump Taj Mahal, Griffin found Trump practically manic. “Donald was a case study in impatience,” Griffin wrote in his memoir. “In his chair, he sat all scrunched up, as if it were a chore for him to remain still. … Periodically, he’d just get up and walk around his office. It was as if he had a blinking sign on his forehead that continually flashed, ‘URGENT! URGENT!’”

As for the Trump Shuttle?

Trump bought and renamed the Eastern Air Lines Shuttle in ‘88 as well. The price he paid was $365 million—again, at least some $60 million too much and maybe more, depending on the estimates and assessments.

With a large, golden pair of scissors, Donald Trump and Congressman Charlie Rangel cut a ribbon during the ceremonies marking the Trump Shuttle’s inaugural flight at Washington National Airport on June 8, 1989. | AP Photo

The negotiations happened in the Oak Room of the Plaza. “I think our number was 375, 385, and he negotiated it down,” Frank Lorenzo, the former Texas Air chairman, who sold Trump the Shuttle, told me in 2016. “The price was too high,” said Bruce Nobles, the former president of the Shuttle under Trump, who was involved in the negotiations. It didn’t matter. “Lorenzo said, ‘I really want to sell it,’ and Donald said, ‘I really want to buy it.’”

Nobles’ recollections of Trump as a negotiator mesh with O’Donnell’s at the casinos. “He was, ‘Here’s my deal, make it happen,’” Nobles said in a recent interview. “All the details, in a very complex deal, Donald wasn’t involved in this at all. He’s always been a big picture guy.” (True, says Trump. “I like to work in broad strokes, deal with the big picture, but not the details,” he once wrote.)

Trump justified his fast, free-spending ways on the Shuttle deal with the same language he used with the Plaza. “I like buying Mona Lisas,” he said.

And all this was when Trump was negotiating from a position of ascendancy and strength.

By 1990, though, Trump’s circumstances had changed. The debts he had accumulated in the late ‘80s—he put no money down for the Plaza and the Shuttle, and he financed the Taj with junk bonds—now were threatening to force him to file for personal bankruptcy. To have a chance to avoid that, one of the things he had to do was build—something—on his 13-block property on the Upper West Side. Up till that point, he had failed to do that, partly because a name-calling feud with New York Mayor Ed Koch meant he didn’t get tax breaks he needed to make the project financially feasible. His leverage now severely diminished, Trump negotiated with neighborhood groups that had drawn up plans for a development that was roughly half the size of what Trump wanted.

“He pretty much gave in to whatever they asked for,” said Res, who was a Trump Organization vice president at the time and involved with the efforts on the Upper West Side. “He was going broke. He really had nothing to bargain with. He caved. And he shouldn’t have—he should have tried. But he lost his nerve.”

She granted: “You know, it’s easy for me to sit here and judge, because it wasn’t my future—it wasn’t my potential bankruptcy. But he hedged his bets. He wasn’t going to take a chance on going bankrupt. I can understand. There was so much at stake for him.”

Looking back, 1990 represents a significant shift in Trump’s approach: There would be no more long-term, multiparty, Commodore-to-Grand Hyatt scenarios. Trump Tower would remain the apex of his deal-making acumen. There were still some good moves—his sale of his majority stake on the Upper West Side to Hong Kong businessmen in 1994 and his bargain-basement acquisition of 40 Wall Street in 1995 proved to be critical money-makers as he clawed his way out of the hole he had created—but Trump’s post-‘90 negotiations increasingly were for comparatively uncomplicated branding and licensing agreements, in which others did the harder legal work while he put his name on labels and made promotional appearances.“ Most of the deals that he did from that point forward,” Latz, the author of The Real Trump Deal, told me, “were relatively straightforward, simple, zero-sum deals.”

If the myth of Trump, negotiator par excellence, started in earnest with the publishing of The Art of the Deal, the prime-time television show in which he starred cemented it. And similar to the deal he struck with Schwartz to write his book, the negotiation that birthed “The Apprentice” was lightning-quick. Trump agreed with producer Mark Burnett to a 50-50 split without consulting any advisers, according to Trump Revealed. And when he attempted to get a giant pay raise after the show’s wildly successful first season, he … didn’t get it.

We ended up paying him what we wanted to pay him.” Jeff Zucker

Trump made $50,000 an episode in the first season. In the second season? “He wanted a million dollars an episode,” Jeff Zucker, the current boss of CNN and former head of NBC, told the New Yorker’s David Remnick last year. And what did Zucker give him? “Sixty thousand dollars,” Zucker said.

“We ended up paying him what we wanted to pay him.”



***

A foundational Trump tenet is to declare success—no matter what. A lifelong devotee of Norman Vincent Peale, he says something and keeps saying it to make it so. Even as his negotiations got less complicated and less effective, Trump never stopped self-identifying as one of the world’s great negotiators.

“We need a negotiator,” Trump said, talking about politics, in 2007 on CNN. “We don’t need sound bites. We don’t need people walking off planes, waving, sitting with a dictator, waving, getting back on the plane, waving, and nothing happens. We need negotiators.”

“So you think you could get in there and negotiate world politics?” he was asked.

“Yes,” he said. “I could do a very good job.”

Now Trump is the president. And the people who know him and have worked with him and the experts who have studied his negotiating skills are unsurprised he’s having some trouble in his new role.

“He’s dealing with people that aren’t just trying to make money,” Blair said. “They’re elected politicians, heads of state, that have their own very demanding constituencies. It’s really very different than a strict dollars-and-cents motivation that he was dealing with before.”

“It takes a tremendous amount of knowledge and experience to get all these people to come together for a common goal. He doesn’t have any experience doing that,” Nobles said. “He just assumed his force of personality would cause people to forget politics. And that’s not the way it works.”

He just assumed his force of personality would cause people to forget politics. And that’s not the way it works.” Bruce Nobles

“There are many more parties,” Res said. “There are many more issues.”

“The environment in which he is negotiating now is radically different from all of his negotiations over the past almost 50 years in business,” Latz told me. The problem, though, is not that they’re different—it’s that Trump doesn’t seem to understand that, or at least isn’t acting like he does.

In spite of his associates’ contentions that he’s “the greatest deal-maker our country’s ever seen” (Corey Lewandowski) and “an amazing negotiator, probably the best in the world” (Michael Cohen), Trump in his first week as president torpedoed negotiations with Mexico about funding the border wall before the talks even began. In the days prior to a scheduled meeting, Trump reiterated that Mexico would pay for the wall, Mexican President Enrique Peña Nieto reiterated that Mexico definitely would not, and Trump tweeted a threat: “If Mexico is unwilling to pay for the badly needed wall,” he mashed into Twitter, “then it would be better to cancel the upcoming meeting.” Which is what Peña Nieto did. “An abject failure,” Latz told me.

Similarly, in the health care negotiations last year, Trump faltered again—due to his overreliance on his “win-lose, zero-sum mindset,” as Latz puts it in his book, in addition to his lack of preparation that resulted in an inability to understand the nuanced policy interests of different sets of Republicans in Congress.

And with North Korea, according to Latz and Malhotra, Trump gave up too much leverage by agreeing so easily to the summit in Singapore. Trump, Malhotra wrote in March for CNBC, “has given the North Korean leader everything he wants,” and that his decision to meet “validates Kim Jong Un’s claim that only a nuclear-armed North Korea will be treated with respect by the Trump administration.”

“What’s the best thing you can say about Donald Trump as a negotiator?” I asked Malhotra recently. This was before Trump canceled on Kim.

There was a long pause.

“What I will say is that at least in the North Korea deal … at least he has tried to leave the door open to say this may not happen,” he said. “He’s realizing, a little bit, that he could get completely trapped. And you don’t want to trap yourself in such a way that the only way to look good is to do something really stupid.”

After Trump indeed backed out last week, Malhotra was “not surprised,” he told me. “He was not going to get a deal that was even close to as good as the Iran deal he killed. So the question was how to get out of the mess.”

Latz said he expects the summit to happen still at some point, and sooner rather than later. Why? Because what made Trump take the meeting in the first place remains the case. With the other negotiating setbacks, the worrisome swirl of the Mueller probe and the midterms mere months away, Trump needs a win. “He got himself into an almost untenable situation from a leverage perspective because he had communicated that he really wanted a deal here,” Latz said. “Despite the fact that Trump canceled and sent the signal he doesn’t really need the deal, he does really need the deal.”

North Korea experts worry about the incoherence and disorganization of Trump and his administration and that they could pay too little attention to tiny but critical details or agree to some type of pact without a firm and enforceable definition of “denuclearization.”

But regardless of what happens from here, a former Trump Organization executive told me, Trump will do what he does. He will try to spin it into a win.

“He believes he’s in a position of strength no matter where or when he is,” the executive said. “You have to understand that. If you knock Donald on his ass, he will tell you the best position to be in is on your ass.”