Trump Dealmaker Image Faces Scrutiny as Record Shows Mixed Results An examination of Donald Trump's dealmaking in business and as president shows mixed results, with many boasts failing to materialize as voters weigh his record in midterm elections. WASHINGTON - Before there was much talk of being a personal brand, Donald Trump had landed on his: the consummate, swashbuckling, never-lose negotiator. 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. It was all about dealmaking prowess. You either have it, or you dont, he said. 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.Now, as he zigzags the country for Republican candidates from Florida to Alaska, Trump is exhorting voters to again embrace him as an unqualified success. The midterm election has become a referendum on his presidency and his record as a dealmaker. An examination of Trumps dealmaking, both in his time in the White House and in the private sector, shows decidedly mixed results.Presidential Deal Making Results MixedHes 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. As president, Trumps boasts of deals have not materialized. He insisted that Iran would be defeated in mere weeks. He later brokered what he called a great ceasefire, though 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 Russias war in Ukraine in a day. He announced an agreement that he said meant Moscow and Kyiv would not attack each others energy infrastructure.That pause never happened, even as the president insisted it would hold. I said, You agreed, Trump said in defending his assertions. Thats why. Trump promised he would use the threat of tariffs to 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 trade wars with Americas close friends, including Canada. The levies brought in more than US$83 billion this year through September, much of it paid for by American consumers and still far less federal revenue than Trump suggested. Even on less consequential matters, Trumps deals have foundered.He said he had a guy whos unbelievable at doing swimming pools who could fix the Lincoln Memorials Reflecting Pool for a little more than US$1 million. The cost has been closer to US$20 million so far. The presidents public acts typically mirror a well-traveled private sector pattern. 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. 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. Theres a certain bit of tap dancing around those details that he just cant do given whats happening in the world today.Television Reinvented Trump Dealmaker PersonaTrumps core narrative as master dealmaker had begun to fade until The Apprentice debuted in 2004. Allowed to play a rich and powerful tycoon on television, Trump rebooted his dealmaker persona.That image of wealth and success helped launch his first presidential run because people feel like, Well, if hes 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. But 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 OBrien, author of TrumpNation: The Art of Being The Donald, said Trump may finally find out after Election Day on Nov. 3 how much voters believe that hes 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 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, Latz said. Trump has long been guided by the notion that he can only win.Negotiation Experts Criticize Trump EgoHe could be a better negotiator if his ego didnt 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 cant make.Then, with the other parts of it, nothing can continue. He just has to win everything. 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 having the U.S. take a stake in the Union Pacific-Norfolk Southern rail merger.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 that Trump is the Dealmaker in Chief - before it fell apart. Trump has credited his own negotiating chops with helping to lower prescription drug prices and stimulate domestic manufacturing.The White House also promotes his dealmaking success. The midterm elections will show how much voters believe the image.