Analysis: Trump says he's a great dealmaker. His record says otherwise

Trump Tower had just opened and The Art of the Deal was three years from publication when 38-year-old Donald Trump suggested he could negotiate Russian arms control better than Ronald Reagan.

“It would take an hour-and-a-half to learn everything there is to learn about missiles,” Trump told The Washington Post in 1984. Of dealmaking prowess, he said, “You either have it, or you don’t.”

Before there was much talk of a personal brand, Trump had landed on his: the consummate, swashbuckling, never-lose dealmaker.

As he zigzags the country for Republican candidates, from Florida to Alaska, Trump is exhorting voters to again embrace him as an unqualified success in a midterm election that has become a proxy referendum on his presidency and his record as a dealmaker.

“He’s not as good at this as he thinks he is,” said Christopher Preble, senior fellow and director of the Reimagining US Grand Strategy programme at the Stimson Center, an international security think tank.

He insisted that Iran would be defeated in mere weeks. He later brokered what he called a “great” ceasefire, although it quickly fizzled. Trump repeatedly has said Tehran is desperate to make a deal to end fighting. That also proved untrue.

He promised to negotiate an end to Russia’s war in Ukraine in a day but hasn't. He now has turned to Moscow to buy diesel.

Trump also said he would use the threat of tariffs to negotiate the best trade deals ever, only to offer unilateral duties that have raised domestic prices and led to a trade war with Canada.

Even less consequential deals have foundered.

Trump said he had a “guy who’s unbelievable at doing swimming pools” who could fix the Lincoln Memorial’s Reflecting Pool for a little more than $1 million. The cost has been closer to $20 million.

His public acts usually mirror a well-travelled private sector pattern. Much of Trump’s career as a developer relied on his making agreements that turned into bad financial bets and led to bankruptcy.

He frequently boasted about doing better in negotiations than he really had, then tried to cover expensive missteps by refusing to pay people working for him, often suing them. His biggest successes came when he had maximum leverage.

Trump’s core narrative as master dealmaker had begun to fade until The Apprentice debuted in 2004. Trump was then allowed to play a rich and powerful tycoon on television, and reboot his dealmaker persona.

Marty Latz, a negotiation expert and author of The Real Trump Deal: An Eye-opening Look At How He Really Negotiates, said Trump the businessman saw every negotiation as a zero-sum game.

“The reality is, he did negotiate some excellent deals, but also that he did fail spectacularly in a number of deals, and that he has never really successfully negotiated as president in a significant number of contexts,” said Latz.

Trump has long been guided by the notion that he can only win.

“He could be a better negotiator if his ego didn’t get in the way,” said Barbara Res, a former executive vice president in charge of construction at the Trump Organisation, who also wrote Tower of Lies.

That spotty record has not stopped Trump from bragging about his dealmaking prowess. Top officials in his administration have rushed to reinforce the idea.

“Downplaying President Trump’s record as a dealmaker-in-chief would require overlooking the nearly 20 trade agreements he successfully negotiated and the trillions of dollars in announced manufacturing investments secured during his presidency," White House spokesperson Matthew Middleton said in a statement.

Some good deals include Trump's first-term Abraham Accords and a ceasefire agreement that ended fighting between Israel and Hamas.

Tim O’Brien, author of TrumpNation: The Art of Being The Donald, said Trump has long sought to create unpredictability in negotiations, viewing them as an extension of his ego: “If he’s the one causing the chaos, he’s often the only one who can end it.”

The Republican president describes his negotiating style as following his instincts and pushing for everything he can imagine, then not stopping until he gets it.

“I aim very high, and then I just keep pushing and pushing and pushing to get what I’m after,” he said in The Art of the Deal.

Res said she and others on Trump’s team would often use performative tactics to keep him happy. Trump Organisation officials would meet with construction managers or subcontractors and settle on their best price, they then would bring them to Trump so he could officially sign off on the deal.

Before the Trump meeting, Res said she often would advise those she had already negotiated with to add a small percentage to their asking price. That way, Trump could get them to agree to a lower price and feel like he’d won something.

Trump also thrived in another area most successful business leaders do not: going to court constantly, either by refusing to pay those working for him and filing lawsuits, or getting sued.

That was another strategic choice, Latz said, because doing so often let him reduce his own costs or to settle with his creditors for far less than he actually owed.

All told, Trump was involved in 4000-plus pieces of litigation over 40 years of business.

That was not “a matter of whether he’s right, or whether he can win", Res said. "The power of being able to manipulate the legal system is terrifying.”