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President Donald Trump speaks in the Diplomatic Reception Room of the White House in Washington on Nov. 15, 2017.

Pablo Martinez Monsivais/The Associated Press

Donald Trump wanted a deal so badly he could taste it. He badgered the person on the other side of the negotiation, pressing for a decision for months. But his adversary would not yield, denying Mr. Trump what he desperately wanted. So Mr. Trump fired back: The decision was "ludicrous" and "disgraceful," and the decision-maker a "disaster" and a "moron."

Sound familiar?

More than 30 years have passed since Mr. Trump tangled with New York mayor Ed Koch over a real estate project in Manhattan, but the dynamics could have been ripped from today's headlines. Now the negotiating style that Mr. Trump honed over decades in business is being tested on the global stage.

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So far, Mr. Trump's deal-making style has not yielded results in the form of major legislation in Congress. In international affairs, his preferred approach has been to withdraw from agreements such as the Paris climate change accord and the Trans-Pacific Partnership. The exception – for now – is the North American free-trade agreement. Mr. Trump is seeking to renegotiate the deal but has repeatedly threatened to terminate it.

How Mr. Trump functions as negotiator-in-chief will have repercussions for his administration and the world. His past reveals that he loves bluster and threats but also likes to turn on the charm; that he is constantly angling for advantage in negotiations, up to the last minute and beyond; and that he seeks to package almost any outcome as a victory.

As a new round of NAFTA talks opens on Friday, Mr. Trump's biographers have a word of caution. "He's never going to be generous and take a larger view," said Gwenda Blair, who wrote a book about Mr. Trump and his family. "He doesn't care about lifting all the boats. He's concerned about his boat."

Mr. Trump's approach "has always been to push and push and push until the other side backs down," said Tony Schwartz, who wrote the bestseller The Art of the Deal with Mr. Trump. "That doesn't work every time, but it certainly worked for him many times in his career. He outlasts people, wears them down."

Mr. Schwartz's advice? Decide what is acceptable and what is not acceptable before opening a negotiation with Mr. Trump and be perfectly clear about it. "If Trump smells blood, God save you," he said.

Here is a sample of Mr. Trump's past negotiating strengths and weaknesses:

1. He makes brash demands

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At the turn of the century, Mr. Trump was embarking on a new chapter in his career. After a debt-fuelled acquisition spree in the 1980s brought him to the brink of personal bankruptcy, Mr. Trump spent the next decade digging his way out of the wreckage (four Trump companies filed for bankruptcy protection in the 1990s). Then in 2003, he decided to try his hand at reality television. The Apprentice, starring Mr. Trump, was a massive success.

Before the second season of the hit show began, wrote Tim O'Brien in his book TrumpNation, Mr. Trump told NBC he wanted a raise – from $50,000 (U.S.) an episode to a whopping $18-million. The "coin toss with NBC was vintage Donald," wrote Mr. O'Brien. "Zoom in for the jackpot. Be outrageous in your demands. Keep a straight face. See what happens. Keep a straight face. Pretend you knew exactly what would happen all along." NBC raised Mr. Trump's per-episode fee to more than $1.25-million, the star told Mr. O'Brien.

Sometimes Mr. Trump's swagger could leave his negotiating partners dumbfounded. In the 1970s, New York planned to build a convention centre on a site controlled by Mr. Trump and his father, Fred Trump. Mr. Trump told the city that he was owed millions of dollars in fees, but he would forgo them if New York named the convention centre after his father.

A few weeks later, city employees examined the terms of the contract in question and discovered that Mr. Trump was not entitled to anywhere near the fee he had claimed, wrote Mr. O'Brien. Mr. Trump's bravado was "unbelievable," the city official who negotiated with Mr. Trump later said. "He almost got us to name the convention centre after his father in return for something he never really had to give away."

Mr. Trump's penchant for exaggerating his own deals exasperated some of his colleagues. Edward Gordon, a major real estate broker, described to Ms. Blair in her book how Mr. Trump would inflate the size of certain purchases without remembering that Mr. Gordon himself had handled the transactions.

"He'll double the numbers on me, and it's a deal I did for him," Mr. Gordon said. "I'll say, 'What are you doing, I did the [expletive] deal' – and he'll say, 'Oh, oh, yes.' But he believes it. … that's his strength and his weakness."

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(Mr. Trump's negotiating style – which one biographer said involved "grandiloquence, convenient slips of memory, and liberal doses of flattery" – has not endeared him to U.S. legislators, for instance, during the effort to repeal the health-care law known as Obamacare. "He's not seen as someone who understands policy," said Frances Lee, a political scientist at the University of Maryland and an expert on Congress. "They don't take his statements at face value.")

2. He always declares victory

Perhaps the most consequential negotiations of Mr. Trump's career took place in May and June of 1990. Mr. Trump was drowning in more than $3-billion of debt – a chunk of which he had personally guaranteed – and he was about to default on several payments.

He initiated talks with a consortium of banks that held the debt and "personally injected himself into the bargaining – sitting with the major banks for 12-hour stretches," wrote Wayne Barrett, Mr. Trump's first biographer. He also turned on the charm, at one point taking orders for shakes and burgers. But he also reminded the banks of his leverage: They all had an interest in seeing him avoid a long, drawn-out bankruptcy proceeding. "His debts were so big that everyone in the room was afraid to see him fall," wrote Ms. Blair. A bluff by Mr. Trump about striking a side deal with a different bank also helped, noted Mr. Barrett.

To nearly all observers, Mr. Trump remained relentlessly positive even as he teetered close to ruin (his first marriage, to Ivana Trump, had also just collapsed). Mr. Trump and the banks reached a deal in which they seized some of his assets, placed liens on other possessions and put a limit on his monthly spending.

"It was the greatest deal I ever made because I saw the world collapsing, and instead of waiting a year, I took my pride and I said the hell with it," Mr. Trump said years later, Michael Kranish and Marc Fisher wrote in their 2016 biography Trump Revealed. During the signing of the final documents, Mr. Trump autographed copies of his new book – Surviving at the Top – and handed them out to those present.

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Mr. Trump's determination to portray every outcome as a victory has faced challenges in the first year of his presidency. "This is a guy who has to win," said Ms. Blair. "He cannot not win." After Mr. Trump's failure to repeal and replace Obamacare, he shifted the blame to his fellow Republicans and vowed to hold Democrats responsible for the program.

3. He can be irrational

At times during his career, Mr. Trump negotiated deals – or refused them – for reasons that were not centred on rational calculation. In 1988, Mr. Trump bought the storied Plaza Hotel in New York for $407.5-million, a record for a hotel at the time. "This isn't just a building, it's the ultimate work of art," Mr. Trump said. "I was in love with it." He later wrote, "When a place like the Plaza is on the block, the toughest negotiators become soft, and logic often gets tossed out the window."

Mr. Trump also developed attachments to what he saw as belonging to him. "As much as he liked to buy, Donald found it almost impossible to sell, even when extraordinary deals came his way," wrote Mr. O'Brien. Mr. Trump balked at the last minute after negotiating a transaction to sell his option on a prime piece of Manhattan land in 1989 for $550-million. Not long after, the real estate market tanked.

Whether Mr. Trump will develop a similar devotion to certain policies or courses of action as President remains to be seen. "There's something emotional that won't allow him to [sell]," a person who negotiated deals with Mr. Trump told Mr. O'Brien. "He always believed there's another penny behind every offer he gets, so he won't let go."

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