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Trump Tower had just opened and \u201cThe Art of the Deal\u201d three years from publication when 38-year-old\u00a0Donald Trumpsuggested he could negotiate Russian arms control better than Ronald Reagan.<\/p>\n
\u201cIt would take an hour-and-a-half to learn everything there is to learn about missiles,\u201d Trump told The Washington Post in 1984. It was all about dealmaking prowess. \u201cYou either have it, or you don\u2019t,\u201d he said.<\/p>\n
Before there was much talk of being a personal brand, Trump had landed on his: the consummate, swashbuckling,\u00a0never-lose\u00a0negotiator.<\/p>\n
It was an image he cultivated in the New York tabloids and later on reality TV, repeating it so often that, to his supporters, perception became reality.<\/p>\n
Now, as he\u00a0zigzags the country\u00a0for Republican candidates, from Florida to\u00a0Alaska, Trump is exhorting voters to again embrace him as an unqualified success in a\u00a0midterm election\u00a0that has become a referendum on his presidency and his record as a dealmaker.<\/p>\n
An examination of Trump\u2019s dealmaking, both in his time in the White House and in the private sector, shows decidedly mixed results.<\/p>\n
\u201cHe\u2019s not as good at this as he thinks he is,\u201d said Christopher Preble, senior fellow and director of the Reimagining U.S. Grand Strategy program at the Stimson Center, an international security think tank.<\/p>\n
He insisted that Iran would be defeated\u00a0in mere weeks. He later\u00a0brokered what he called a \u201cgreat\u201d ceasefire, though it quickly fizzled. Trump repeatedly has said Tehran\u00a0is desperate\u00a0to make a deal to end fighting. That also proved untrue.<\/p>\n
He promised to negotiate an end to\u00a0Russia\u2019s war in Ukraine\u00a0in a day. He announced an agreement that he said meant Moscow and Kyiv would not attack each other\u2019s energy infrastructure. That pause never happened, even as the president insisted it would hold. \u201cI said, \u2018You agreed,\u2019\u201d Trump said in defending his assertions. \u201cThat\u2019s why.\u201d<\/p>\n
Trump promised he would use the threat of\u00a0tariffs\u00a0to negotiate the best trade deals ever, only to offer unilateral duties nearly the whole world over. Those import taxes have raised domestic prices and sparked\u00a0trade wars with America\u2019s close friends, including Canada. The levies brought in\u00a0more than $83 billion\u00a0this year through September, much of it paid for by American consumers and still far less federal revenue than Trump suggested.<\/p>\n
Even on less consequential matters, Trump\u2019s deals have foundered. He said he had a \u201cguy who\u2019s unbelievable at doing swimming pools\u201d who could\u00a0fix the Lincoln Memorial\u2019s Reflecting Pool\u00a0for a little more than $1 million. The cost has been closer to $20 million so far.<\/p>\n
The president\u2019s public acts typically mirror a well-traveled private sector pattern.<\/p>\n
He frequently boasted about doing better in negotiations than he really had, then sought to cover expensive missteps by refusing to pay people working for him, often suing them. His biggest successes came when he had maximum leverage.<\/p>\n
\u201cYou can spin a real estate deal, as, \u2019Oh, you know, I got the better part of the deal because I bought it for this much and I sold it for this much,\u2019\u201d Preble said. \u201cThere\u2019s a certain bit of tap dancing around those details that he just can\u2019t do given what\u2019s happening in the world today.\u201d<\/p>\n
Trump\u2019s core narrative as master dealmaker had begun to fade until \u201cThe Apprentice\u201d debuted in 2004. Allowed to play a rich and powerful tycoon on television, Trump rebooted his dealmaker persona.<\/p>\n
That image of wealth and success helped launch his first presidential run \u201cbecause people feel like, \u2018Well, if he\u2019s the president some of that success and wealth is gonna rub off on me,\u2019\u201d said Joel Penney, a professor at Montclair State University who studies the intersection of pop culture and politics.<\/p>\n
But even now, as his\u00a0approval ratings have sunk to near-historic lows, Trump still insists he is among the best dealmakers the world has known.<\/p>\n
Tim O\u2019Brien, author of \u201cTrumpNation: The Art of Being The Donald,\u201d said Trump may finally find out after Election Day on Nov. 3 \u201chow much voters believe that he\u2019s a competent manager and a great dealmaker.\u201d<\/p>\n
Marty Latz, a negotiation expert and author of \u201cThe Real Trump Deal: An Eye-opening Look At How He Really Negotiates,\u201d said Trump the businessman saw every negotiation as a zero-sum game.<\/p>\n
\u201cThe 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,\u201d Latz said.<\/p>\n
Trump has long been guided by the notion that he can only win.<\/p>\n
\u201cHe could be a better negotiator if his ego didn\u2019t get in the way,\u201d said Barbara Res, a former executive vice president in charge of construction at the Trump Organization, who wrote \u201cTower of Lies: What My Eighteen Years of Working with Donald Trump Reveals about Him.\u201d \u201cAny concession that should be made, he can\u2019t make. Then, with the other parts of it, nothing can continue. He just has to win everything.\u201d<\/p>\n
Top officials in the Trump administration go to great lengths to amplify the idea that he is a master negotiator.<\/p>\n
\u201cI make one of those deals every day that no normal person would make,\u201d the president said in May, defending having the U.S. take a stake in the Union Pacific-Norfolk Southern rail\u00a0merger.<\/p>\n
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 \u201cthe dealmaker in chief.\u201d<\/p>\n
Republican South Carolina Sen. Tim Scott posted on X that the ceasefire with Iran \u201conce again\u201d proved that Trump \u201cis the Dealmaker in Chief\u201d \u2014 before it fell apart.<\/p>\n
Trump has credited his own negotiating chops with helping to\u00a0lower prescription drug prices\u00a0and stimulate\u00a0domestic manufacturing. The White House also pointed to a long list of trade agreements that Trump announced since last year with China, Japan and countries across Europe, Southeast Asia and elsewhere.<\/p>\n
White House spokesman Matthew Middleton said \u201cthis administration will continue advancing an America First economic agenda.\u201d<\/p>\n
\u201cDownplaying President Trump\u2019s 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,\u201d Middleton said in a statement.<\/p>\n
The president\u2019s ledger also includes successes such as his first-term\u00a0Abraham Accords\u00a0and a\u00a0ceasefire agreement\u00a0that ended fighting between Israel and Hamas in Gaza \u2014 though\u00a0strikes, raids and killingshave continued there ever since. Neither deal succeeded in achieving\u00a0larger and lasting Middle East peace\u00a0as Trump predicted they would, though.<\/p>\n
An agreement on\u00a0civil nuclear cooperation with Saudi Arabia\u00a0is in the early stages. An accord allowing the U.S. to\u00a0help tap Venezuela\u2019s petroleum reserves\u00a0that Trump calls \u201cprobably it\u2019s the biggest deal in the history of our country\u201d will similarly take years to pay dividends \u2014 if it ever does.<\/p>\n
O\u2019Brien said Trump long sought to create unpredictability in negotiations, viewing them as an extension of his ego: \u201cIf he\u2019s the one causing the chaos, he\u2019s often the only one who can end it.\u201d<\/p>\n
The president describes his negotiating style as following his instincts and pushing for everything he can imagine, then not stopping until he gets it.<\/p>\n
\u201cI aim very high, and then I just keep pushing and pushing and pushing to get what I\u2019m after,\u201d he said in \u201cThe Art of the Deal\u201d with ghostwriter Tony Schwartz, who later became so disillusioned that he noted that Trump did not write the book and may not have even read it.<\/p>\n
Published in November 1987, \u201cThe Art of the Deal,\u201d nonetheless made Trump nearly as well-known for his appearances on \u201dLifestyles of the Rich and Famous\u201d as any real estate venture. \u201cWe need a leader that wrote \u2018The Art of the Deal,\u2019\u201d Trump declared when launching his 2016 presidential run.<\/p>\n
Latz said Trump has changed the way he pursued deals when he was in the business world since returning to the White House in 2025, automatically assuming that the power of the presidency \u201ctranslates to negotiation leverage.\u201d<\/p>\n
And a business negotiation is far different from one involving multiple countries, Latz said, like the Russia-Ukraine war and the conflict with Iran, where superior military might is not always enough.<\/p>\n
\u201cWe may have conventional power,\u201d Latz said, \u201cand yet we may not have power at negotiation. Donald Trump used to understand that.\u201d<\/p>\n
In business, the stakes were markedly lower, and his showmanship was not always in public view.<\/p>\n
Res said she and others on Trump\u2019s team would often use performative tactics to keep him happy.<\/p>\n
Before meeting with Trump, 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 had won something.<\/p>\n
\u201cWe did that because we knew he wanted to feel that he was better than everybody,\u201d she said.<\/p>\n
Trump also thrived in another area most successful business leaders do not \u2014 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.<\/p>\n
It meant \u201ctaking advantage of a system which many of us would think is morally wrong,\u201d Latz said. \u201cBut it reflected an understanding of leverage.\u201d<\/p>\n
All told, Trump was involved in 4,000-plus pieces of litigation over 40 years of business, which meant even his best deals \u201cresulted in suing,\u201d Latz said, \u201cAnd that\u2019s not a coincidence.\u201d<\/p>\n
That practice has continued right into Trump\u2019s presidency, as lawsuits remain active against everyone from\u00a0the BBC\u00a0to\u00a0JPMorgan Chase.<\/p>\n
Res said it was not \u201ca matter of whether he\u2019s right, or whether he can win. The power of being able to manipulate the legal system is terrifying.\u201d She said Trump avoided signing \u201ca contract that allows for arbitration\u201d in favor of court and then, cases take so long, that \u201cpeople can go bankrupt in the first year if they don\u2019t play the game his way.\u201d<\/p>\n<\/div>\n
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