Trump Is Actually Lousy at Making Deals, According to Negotiation Experts

After the president caved and ended the shutdown without getting a wall, it's clearer than ever he's not a master negotiator.
Donald Trump

On Friday afternoon, as Donald Trump agreed to a deal to reopen the federal government without getting the border wall funding he was demanding, it was hard to forget that his celebrity was originally founded upon his prowess as a dealmaker. This personal mythos built his brand in the 80s and was a major element of his presidential campaign. But the shutdown put a major dent in that reputation, as he got most of the blame for the resulting chaos from the public and struggled to put pressure on the Democrats.


Just before Trump announced that he would agree to a funding bill that would keep the government open for three weeks while Congress debates border security and immigration issues, VICE spoke with a number of experts in the art and science of negotiation to get their take on how the president has been managing these talks. Was there some genius behind all the chaos, or did 800,000 federal workers go without pay for weeks because Trump really is just a horse running loose through a hospital?

To properly analyze Trump’s handling of the shutdown, it makes sense to look at his past. G. Richard Shell, a legal studies and business ethics and management professor at Wharton and author of many books on negotiation, recently did a deep dive into what molded the president’s approach to deal making for a special issue of Harvard's Negotiation Journal. Shell pointed to two foundational elements he believes are the keys to understanding Trump’s brand of deal-making

“First, you’ve got to understand that he didn't really actually negotiate that much himself,” said Shell of Trump’s real estate heyday. “He had a team of lawyers out, principally in the 70s and 80s. Two main lawyers: Roy Cohn as his litigator and a guy named George Ross who was his deal-maker.”

According to Shell, while Trump leveraged his rolodex to schmooze mayors for permits or manage relationships with the banks and money guys, his legal soldiers hammered out the granular details behind closed doors. Lacking a comparable brain trust today, Trump is less likely to see his big-picture ideas realized.


“Facet number two is he trusts nobody and he's never trusted anybody,” continued Shell. “When you are deeply and utterly suspicious of other people, always, even the ones who have been your friends that are close to you, that makes the whole world pretty transactional. It's a predatory environment that he imagines himself to be in and there's not a lot of human kindness or compassion or long-term trust in there.”

Shell believes these factors have resulted in an issue for Trump’s private-backroom-deal style, compounding his inexperience in the more public and nuanced wheeling and dealing of DC. "I would go back to the two things George Ross taught us about how to successfully negotiate with Trump: Assume there are no rules and stand your ground," said Shell following Trump's shutdown-ending announcement. "[House Speaker] Nancy Pelosi seems to have instinctively understood this. She gained his respect (he can’t even come up with a nickname for her other than 'Nancy'), he sensed he was losing his leverage, and he backed down while saying that he was really just declaring a truce in a war he would certainly win later."

Josh Weiss, a senior fellow at Harvard’s Negotiation Project, noted that when approaching any negotiation, one must consider all parties’ interests and positions, “positions being what people want, interests why they want those things.”

Trump's position on a wall was relatively clear, but his motivations are more complicated. The crux of the issue revolves around border security and immigration but, as is often the case in politics, the public-facing motivations may be masking others. Weiss thinks that Trump may have “painted himself into a corner” with his wall campaign promise, and now that he’s hitched his entire presidency to getting one constructed, he may never agree to a long-term deal that doesn’t give him that win to bring back to his base.


“In most negotiations you have constituents that you have to go back to,” explained Weiss. “So we talk about what your victory speech will look like and, if you can't write one, it's very likely that the deal's not going to work.”

The ongoing negotiations over the wall present a challenge, because Trump is so determined to build a wall and Democrats are so determined to stop him. But Weiss noted that “one way out of a single-issue negotiation block is to try to think more broadly about adding in other issues so that people can turn around and say, ‘Look, this is what we really wanted to get.’” While Trump's offers last weekend were clearly non-starters for the Democrats, the experts I spoke to thought that more significant immigration reform concepts could ultimately provide a way out.

“This is being treated as a classic distributive negotiation, like ‘I either get this or I don't,’” said Parker Ellen, an assistant professor of management and organizational development at Northeastern University. “The only way you get a deal on that is if somebody is willing to move off of their position and make some concessions and right now, the only concessions with the proposals that have been made have not included the fundamental position of conflict, which is wall or no wall.”

The shutdown started because initially, both Trump and the Democrats thought they had leverage to get the other side to cave. “There’s the concept of BATNA, which stands for your 'best alternative to a negotiated agreement,'” explained Weiss. “In any negotiation, you want to be able to answer that question. If I sit down with somebody and we don't reach agreement, what happens then, where do I go from here?”


Initially, both sides believed that their BATNA of “no agreement” was better than a compromise that showed they were giving in. But as the shutdown dragged on, with angry federal workers unpaid, government functions not being performed, and flights being grounded thanks to air traffic controller shortages, Trump evidently felt pressure to bring this to an end.

William Ury, the co-author of Getting to Yes, one of the better-known books on negotiation, feels that the public, who he refers to as “the third side,” shouldn't discount its own role in ending the shutdown.

"It’s the felt pressure of the 'third side' on the parties which leads to this opening," said Ury. "Once in the negotiation process, it will be harder to get off like when you get on an escalator. The likelihood is of an agreement."

Ultimately, even if Trump never gets his wall, Ury, believes his showmanship and ability to spin may prove more important than his negotiating skills. Whatever abilities the president lacks, he's “extremely talented at framing things as a victory even though, for other people, it wouldn't seem that way.”

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