When Trump Tower had just opened, and “The Art of the Deal” was still three years from publication, a 38-year-old Donald Trump suggested he could handle Russian arms control better than President 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. To him, it was all about dealmaking prowess. “You either have it, or you don’t,” he said.

Long before “personal brand” entered the mainstream lexicon, Trump had settled on his: the consummate, swashbuckling, never-lose negotiator. He cultivated that image in the New York tabloids and later on reality television, repeating it so often that, for his supporters, perception became reality.

Now, as he zigzags the country on behalf of Republican candidates from Florida to Alaska, Trump is urging voters to once again embrace him as an unqualified success in a midterm election that has become a referendum on his presidency and his record as a dealmaker. Every seat in the House of Representatives and roughly a third of the Senate is on the ballot.

Yet an examination of Trump’s dealmaking — in both the White House and the private sector — shows decidedly mixed results.

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

Deals that didn’t hold

Trump insisted that Iran would be defeated in mere weeks. He later brokered what he called a “great” ceasefire, though it quickly fizzled. He repeatedly claimed Tehran was desperate to make a deal to end the fighting. That, too, proved untrue.

He promised to negotiate an end to Russia’s war in Ukraine in a day, and announced an agreement he said meant Moscow and Kyiv would not attack each other’s energy infrastructure. That pause never happened, even as the president insisted it would hold. “I said, ‘You agreed,’” Trump said in defending his assertions. “That’s.”

On trade, Trump promised the threat of tariffs would secure the best deals ever, only to impose unilateral duties on nearly the entire world. Those import taxes have raised domestic prices and ignited trade wars with some of America’s closest friends, including Canada. The levies brought in more than $83 billion this year through September — much of it paid by American consumers, and still far less federal revenue than Trump suggested.

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, a landmark on the National Mall, for a little more than $1 million. The cost so far has been closer to $20 million.

A familiar pattern from the private sector

The president’s public record typically mirrors a well-traveled pattern from his business career. He frequently boasted of having negotiated better terms than he actually had, then sought to cover expensive missteps by refusing to pay people who worked for him — often suing them. His biggest successes came when he held maximum leverage.

“You can spin a real estate deal, as, ’Oh, you know, I got the better part of the deal because I bought it for this much and I sold it for this much,’” Preble said. “There’s a certain bit of tap dancing around those details that he just can’t do given what’s happening in the world today.”

Trump’s core narrative as master dealmaker had begun to fade until the NBC reality show “The Apprentice” debuted in 2004. Allowed to play a rich and powerful tycoon on television, he rebooted his dealmaker persona. That image of wealth and success helped launch his first presidential run.

“People feel like, ‘Well, if he’s the president some of that success and wealth is gonna rub off on me,’” said Joel Penney, a professor at Montclair State University who studies the intersection of pop culture and politics.

Even now, as his approval ratings have sunk to near-historic lows, Trump still insists he is among the best dealmakers the world has known. Tim O’Brien, author of “TrumpNation: The Art of Being The Donald,” said Trump may finally find out after Election Day on Nov. 3 — the first nationwide vote since he returned to the White House in 2025 — “how much voters believe that he’s a competent manager and a great dealmaker.”

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 treated 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,” Latz said.

‘He just has to win everything’

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 Organization, who wrote “Tower of Lies: What My Eighteen Years of Working with Donald Trump Reveals about Him.” “Any concession that should be made, he can’t make. Then, with the other parts of it, nothing can continue. He just has to win everything.”

The White House pushes back

Top officials in the Trump administration go to great lengths to amplify the idea that he is a master negotiator.

“I make one of those deals every day that no normal person would make,” the president said in May, defending the U.S. taking a stake in the Union Pacific-Norfolk Southern rail merger, a combination of two of the country’s largest railroads.

A parade of advisers — including former White House press secretary Karoline Leavitt, Commerce Secretary Howard Lutnick and Interior Secretary Doug Burgum — have all labeled Trump “the dealmaker in chief.” Republican South Carolina Sen. Tim Scott posted on X that the ceasefire with Iran “once again” proved Trump “is the Dealmaker in Chief” — before it fell apart.

Trump has credited his negotiating skills with helping to lower prescription drug prices and stimulate domestic manufacturing. The White House has also pointed to a long list of trade agreements Trump has announced since last year with China, Japan and countries across Europe, Southeast Asia and elsewhere.

White House spokesman Matthew Middleton said “this administration will continue advancing an America First economic agenda.”

“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,” Middleton said in a statement.

A mixed ledger

The president’s ledger also includes successes such as his first-term Abraham Accords, which normalized relations between Israel and several Arab countries, and a ceasefire agreement that ended fighting between Israel and Hamas in Gaza — though strikes, raids and killings have continued there ever since. Neither deal achieved the larger, lasting Middle East peace Trump predicted.

An agreement on civil nuclear cooperation with Saudi Arabia is in the early stages. An accord allowing the U.S. to help tap Venezuela’s petroleum reserves — a deal Trump calls “probably it’s the biggest deal in the history of our country” — will likewise take years to pay dividends, if it ever does.

Chaos as a negotiating tool

O’Brien 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 president describes his negotiating style 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,” written with ghostwriter Tony Schwartz, who later became so disillusioned that he pointed out Trump did not write the book and may not have even read it.

Published in November 1987, “The Art of the Deal” nonetheless made Trump nearly as well known for his appearances on ”Lifestyles of the Rich and Famous” as for any real estate venture. “We need a leader that wrote ‘The Art of the Deal,’” Trump declared when launching his 2016 presidential run.

Business leverage vs. presidential power

Latz said Trump has departed from the way he pursued deals in the business world since returning to the White House in 2025, automatically assuming that the power of the presidency “translates to negotiation leverage.” A business negotiation is far different from one involving multiple countries, he added, pointing to the Russia-Ukraine war and the conflict with Iran, where superior military might is not always enough.

“We may have conventional power,” Latz said, “and yet we may not have power at negotiation. Donald Trump used to understand that.”

Staged victories

In business, the stakes were markedly lower, and the showmanship was not always in public view. Res said she and others on Trump’s team often used performative tactics to keep him happy. Before meeting with Trump, she said, she would frequently advise counterparties she had already negotiated with to pad their asking price by a small percentage. That way, Trump could talk them down to a lower price and feel he had won something.

“We did that because we knew he wanted to feel that he was better than everybody,” she said.

Litigation as strategy

Trump also thrived in an arena most successful business leaders avoid: constant court battles, whether by refusing to pay people who worked for him and filing lawsuits, or by getting sued. Latz said that, too, was a strategic choice, because litigation often allowed him to reduce his own costs or settle with creditors for far less than he actually owed. It meant “taking advantage of a system which many of us would think is morally wrong,” Latz said. “But it reflected an understanding of leverage.”

All told, Trump was involved in 4,000-plus pieces of litigation over 40 years of business, meaning even his best deals “resulted in suing,” Latz said. “And that’s not a coincidence.”

That practice has continued straight into his presidency, with lawsuits still active against everyone from the BBC to JPMorgan Chase.

Res said it was never “a matter of whether he’s right, or whether he can win. The power of being able to manipulate the legal system is terrifying.” She said Trump avoided signing “a contract that allows for arbitration” in favor of the courts, where cases drag on so long that “people can go bankrupt in the first year if they don’t play the game his way.”

This story was originally featured on Fortune.com.