Why Trump Fails at Making Deals

It is at the very core of his appeal. Since Donald Trump’s improbable run to the White House began in 2015, the real estate magnate has managed to win over U.S. voters—even many who allow they don’t like him personally—by arguing that he’s a master negotiator who will swing a lot of new deals for the American people.

But as the third anniversary of the president’s election approaches, evidence is mounting that Trump has mastered very little internationally. On the contrary, his various high-profile efforts at restarting negotiations with China, Iran, North Korea and other nations have—at least since the signing of his much-mocked makeover of NAFTA in 2018—all run aground. And this week Trump proved himself a dubious dealmaker yet again. He called off his visit to a close U.S. ally, Denmark—a country with a prime minister who’s also a natural political ally, because she’s as anti-immigrant as he is—ostensibly because the Danes refused to consider selling him Greenland (which, technically, may not be Denmark’s to sell anyway, since it is a semi-autonomous territory with its own prime minister).

To many longtime Trump watchers, the president’s poor performance at the diplomatic negotiating table is all of a piece with his overhyped career in business. “Donald’s deal-making skills are a wonderful figment of his own imagination,” said Alan Lapidus, the former architect to the Trump Organization who has known the president since he was a teenager and just starting in the family real estate business.

“His negotiating skill consists of screaming and threatening,” Lapidus told Foreign Policy. “Donald has no subtlety and no sense of humor. It’s bludgeon, bludgeon, bludgeon.”

To the extent that Trump and his business did negotiate successful deals, Lapidus said, it was largely because of the skill of his senior executives such as Harvey Freeman and Susan Heilbron, who handled most of the Trump Organization’s Atlantic City and leasing negotiations. “They did all the detailed analysis and reading, none of which he would ever do.”

Other former Trump business associates say that his frequent boasts about beating the banks at the negotiating table are also overstated; it is widely agreed that the negotiating skill of Trump’s then-chief financial officer, Stephen Bollenbach, is mainly what saved him from a close brush with personal bankruptcy when he was $900 million in debt in 1990.

Michael D’Antonio, a Trump biographer who interviewed him many times, agrees with Lapidus that there is no discernible difference in the way Trump negotiates today, as president, compared to his career in business. “His style involves a hostile attitude and a bullying method designed to wring every possible concession out of the other side while maximizing his own gain,” D’Antonio said. “As he explained to me, he’s not interested in ‘win-win’ deals, only in ‘I win’ outcomes. When I asked if he ever left anything on the table as a sign of goodwill so that he might do business with the same party in the future he said no, and pointed out that there are many people in the world he can work with, one at a time.”

When negotiating with countries rather than companies, however, the situation is different. There are only so many countries in the world, and a president must deal with the major ones again and again, and on many different levels—goodwill counts, in other words. Moreover, countries cannot be driven out of business like competitors in business; they don’t file for bankruptcy and conveniently disappear. There is no zero-sum “Only I win” outcome in trade.

Above all, national pride comes into play—a successful negotiation must leave the other side a face-saving way out. World leaders can’t just surrender and slink off like someone who’s been beaten on a business deal. Trump doesn’t appear to want to make such concessions—even though, at the urging of his son-in-law, Jared Kushner, he reportedly did concede a few points to Canada and Mexico during the talks over the United States-Mexico-Canada Agreement in 2018. (“This agreement would not have happened if it wasn’t for Jared,” Trump’s chief negotiator, U.S. Trade Representative Robert Lighthizer, told reporters at the time.)

“Temperamentally, the president is unprepared for diplomacy and negotiations with sovereign states,” said D’Antonio. “He doesn’t know how to practice the give-and-take that would produce bilateral or multilateral achievements and he takes things so personally that he considers those with a different point of view to be enemies. He is offended when others decline to be bullied and angered by those who counter his proposals with their own ideas.”

Thus Trump is finding that his bludgeoning approach appears to be only driving some interlocutors further into a corner, making agreements even more difficult than when talks began. He started a trade war with China unilaterally—after pulling out of the 12-nation Trans-Pacific Partnership that had created a united front against China—only to find his counterpart, Chinese President Xi Jinping, utterly unmoving on key issues such as state subsidies to business and intellectual property theft, even as markets are signaling that the two-year stalemate threatens the global economy. Trump’s condemnation of the Iran nuclear pact as “the worst deal ever” and attempt to sanction Tehran back to the table—including placing personal sanctions on its chief negotiator, Foreign Minister Mohammad Javad Zarif—has also gone nowhere. Same with his attempt to befriend North Korean leader Kim Jong Un and his botched offer to mediate India’s and Pakistan’s claims to the disputed province of Kashmir so as to ease the U.S. situation in Afghanistan. On one front where Trump might soon be able to achieve some success—negotiations with the Taliban—the president has left the negotiations almost entirely to his envoy, Zalmay Khalilzad, and some experts fear that a promised U.S. withdrawal from Afghanistan will lead only to a Taliban victory.

Trump himself continues to affect unconcern, saying he’s in “no hurry” in most of these cases. Yet again on Wednesday he told reporters “we’re winning” against China and mock-appealed to the heavens, saying, “I am the chosen one.” But he may be running out of time with the 2020 campaign just ahead.

Trump’s lack of success at international negotiations is largely matched on the domestic front. There have been no substantive talks on infrastructure, immigration, or health care, three of his key promises. (He did get a criminal justice reform bill, a Democratic Party agenda item that was again thanks in part to the negotiating skills of his son-in-law, Kushner.) And back in January, Trump completely surrendered to the Democrats over his promised border wall, ending a 35-day government shutdown that he had started, when he agreed to a temporary funding measure that allowed federal employees to return to work but put up no money for his wall.

Trump’s negotiating style is fairly predictable and follows a regular pattern, a combination of what another Trump biographer, Gwenda Blair, calls “bludgeoning and love-bombing.” Against China and Iran, he has been unremittingly critical, leaving Xi and Iranian President Hassan Rouhani almost no way to come to terms without seeming to surrender—which would be politically difficult, if not impossible, for both of them. But he has also tried flattery, tweeting this week that Xi “is a great leader who very much has the respect of his people” and saying of Rouhani at another point: “I am sure he is an absolutely lovely man!”

In dealing with Kim, also, Trump followed up an early slew of threats—at one point he even blasted his then-secretary of state, Rex Tillerson, for “wasting his time” trying to talk to North Korea—with repeated attempts at flattery, summiteering and exchanging private messages with Kim and promising him a “very rich” country if he gives up his nuclear weapons.

Yet neither Trump’s public diplomacy nor the talks with his ministerial-level negotiators have achieved any notable progress—except, perhaps, for Kim, who has gained an unprecedented degree of global recognition and legitimacy for his regime.

From China to Denmark, Trump’s approach is “vintage Donald, trying to get alone in a room with one other person, which of course is why he doesn’t like multilateral treaties or conventions at all,” Blair said. “He wants to be in there with one person so he can really lean on that person.”

The bid for Greenland, Blair said, is also in keeping with Trump’s career path. “Part of what’s going on is that he has only ever been engaged in building a brand,” she said. “First it was Trump Inc., then as a casino magnate, then as a reality TV magnate. Now it’s the president magnate. What better way to build that brand than to buy the world’s largest island?”

Lapidus—whose family ties to Trump go back to the president’s father, Fred Trump, for whom he also worked as an architect—said Trump’s approach here as well is all too familiar to his business associates. “It all flows out of the way he was when he was in business. Everything he’s doing now is an echo of that, starting with the nonstop lying, which at the time I thought was kind of cute.”

Now, as then, Lapidus said, Trump’s negotiating style is all tactics of the moment and no appreciable strategy—which is facilitated by the president’s frequent tweeting. Lapidus recounted a court hearing involving an Atlantic City casino in the 1980s, when he said he felt forced to back up, under oath, Trump’s false account of his reasons for building it.

“Afterward I asked him what he was doing, why he said what he did. He said, ‘Alan, I had no idea what I was going to say until the words came out of my mouth.’ That is Donald Trump.”