I sometimes wonder whether, in contemplative moments late at night, President Trump gazes at a copy of “The Art of the Deal” and hears a quiet but insistent voice telling him that, for all his bluster, he’s actually an absolutely terrible dealmaker. As a businessman, he had enough successful deals to outweigh the disastrous ones, but as a president he has amassed an extraordinary record of failure when it comes to dealmaking:

Anne Gearan and David J. Lynch report:

Nearly three years into his tenure, the president who promised to bring his “Art of the Deal” business savvy to foreign and trade policy has few substantive deals to his name — and he is running short on time to deliver big-ticket agreements ahead of Election Day next year.
Trump has launched or proposed roughly two dozen international negotiations — from bold strokes with North Korea and the Taliban to far-fetched suggestions such as the U.S. purchase of Greenland. So far, the results include no grand bargains, some clear failures and numerous incompletes.

A complete list of the deals foreign and domestic that Trump has promised and then failed to make would be too long for this space, but here are just a few:

  • A trade deal with China
  • A new nuclear deal with Iran
  • A deal to get North Korea to give up its nuclear weapons
  • A deal to end U.S. involvement in Afghanistan
  • A peace deal between the Israelis and the Palestinians
  • A deal to make Mexico pay for a border wall
  • A deal to repeal and replace the Affordable Care Act with “something terrific
  • A deal on new gun-safety measures

You get the idea.

And in what may be remembered as his most important non-deal, Trump apparently tried to make a deal with Ukrainian President Volodymyr Zelensky — you find me dirt on Joe Biden, and I’ll release the military aid Congress appropriated — and the result is that not only did he not get what he wanted, he will likely be impeached because of it.


In short, it has become clear that Trump is in fact the world’s worst negotiator. But why? What is it that makes him so terrible at the kind of dealmaking he thought he’d be able to bring to the presidency?

Trump can’t be bothered to understand his negotiating partners. This is perhaps the single most important factor in a successful negotiation, and Trump displays no interest in it. What does the other side want? What are their incentives? What are they afraid of? Where might they be willing to make concessions, and what won’t they budge on?

Trump doesn’t understand incentives. Trump doesn’t demonstrate any understanding of why Kim Jong Un believes his nuclear weapons are literally the key to his survival, or why certain Republicans in Congress would be hesitant to blow up the Affordable Care Act, or why Xi Jinping has plenty of patience to drag on a trade war.


In his business career, Trump negotiated through domination, seeking partners who had less power and resources than him. He’d order a good or service from a small business, then refuse to pay, or maybe offer half of what he agreed to. Because of the power imbalance, they often gave up.

But that kind of bullying doesn’t work in politics. When he writes President Recep Tayyip Erdogan a childish and threatening letter telling Erdogan not to invade northern Syria, he doesn’t anticipate that Erdogan will react with contempt. Meanwhile, everyone around the world realizes how susceptible Trump is to flattery and uses it to manipulate him.

Trump thinks negotiation is just about personality. Trump is completely bored by the substance of issues. He believes he can just blow in, overwhelm the other side with his magnetic personality and get everything he wants. It keeps failing, but he is undeterred.


Trump thinks everything is zero sum. In everything he does, Trump makes clear his belief that there are only winners and losers, and if you’re not the winner, you’re the loser. But sometimes all sides need to feel that they’ve won. It’s often not at all about winning and dominating but about finding where mutual interests align.

Trump can’t build trust. One key to scams such as Trump University was the fact that there were always more suckers out there who had seen him on TV but didn’t understand who he really was. But now everyone knows who he is.

If you were a foreign leader negotiating with him, would you have any faith that he’d keep a promise? Of course not. The same applies to members of Congress, even Republicans, whose votes he might need. They’ve seen Trump operate, so they can’t assume he won’t change his position. Sen. John Cornyn (R-Tex.) has admitted to this problem.


Trump doesn’t follow through. Trump quickly loses interest if he can’t get a big, splashy — and quick — victory. But some negotiations require intense work over months or even years. Trump tends to bail out of situations that don’t look like they’re going the way he’d like — as the Kurds are now finding out.

When he ran for president, Trump played on — and shared — a naive belief many Americans have about government, that solving policy problems, like creating a new health-care or immigration system, is actually easy. One month in, he said, “Nobody knew that health care could be so complicated." By now he might have realized that political negotiations are far more complicated than trying to get a contractor to knock 10 percent off the cost of some gold-leaf wallpaper, then adjusted his approach accordingly.

But he hasn’t. So all those deals he promised will not be forthcoming.

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