Marty Latz is the founder of LATZ Negotiation and author of the just released book The Real Trump Deal: An Eye-Opening Look at How He Really Negotiates.

When President Donald Trump fired a broadside at NATO allies in Brussels on Wednesday, complaining once again that other nations are not paying their fair share for the alliance’s defense and labeling Germany a “captive of Russia,” he was displaying the same hyperaggressive negotiation style that has defined not only his first 500 days in office but his nearly 50-year business career.

In just the past month, he belittled Canadian Prime Minister Justin Trudeau as “weak” and “dishonest” and vowed to levy taxes “like never before” on iconic U.S. manufacturer Harley-Davidson after learning it might move some manufacturing overseas. He has even mocked members of his own party whom he considered insufficiently loyal, costing him key votes on major legislation.


But this high-volume, public shaming strategy—while winning headlines that play well with his political supporters—hasn’t delivered the negotiating results he has promised.

I have been studying and teaching negotiation for 25 years and, over the past 18 months, have studied over 100 of Trump’s business deals over the course of his almost five decades of negotiating, examining them for evidence of the traits used by history’s most celebrated negotiators. I’ve concluded that the man who made his career promoting himself as the ultimate deal-maker is far less effective than he thinks and often doesn’t negotiate well based on the experts’ proven research.

And his dearth of negotiating skills, unfortunately, will put him in a vulnerable position when he sits across the table from Vladimir Putin in Helsinki next Monday for what he confidently describes as “the easiest” meeting of his overseas trip.

For example, businessman Trump’s lack of patience and attention to detail, and his failure to do his homework led him to overpay by tens of millions for the Trump Shuttle and New York City’s Plaza Hotel in the mid-1980s. And his tit-for-tat public name-calling spat with New York City Mayor Ed Koch likely cost him a real estate deal worth billions with the world’s tallest building that he called “Television City.”

Compare this behavior with the examples of some of his history’s most noted negotiators. James Madison. Madison exhaustively prepared for the Constitutional Convention as he knew he needed to radically change the negotiation agenda from the failing Articles of Confederation to a new governing structure. Nelson Mandela exhibited similarly effective negotiating traits in balancing nonadversarial assertiveness with impressive levels of empathy when—after 27 years in prison—he negotiated an end to apartheid, a new national constitution and a transition to democracy with the white power structure that had imprisoned him. President John F. Kennedy, using strategic patience and creative flexibility, deftly steered two superpowers away from nuclear catastrophe during the Cuban Missile Crisis.

Madison, Mandela and Kennedy exhibited many of the traits that professor Andrea Schneider, head of Marquette Law School’s award-winning dispute resolution program, has found to be the personal characteristics of people who routinely succeed across the negotiating table. She has studied this for over 25 years, and she and other experts have identified five key attributes: assertiveness, empathy, social intuition, flexibility and ethicality.

Effective negotiators exhibit high levels of assertiveness, the ability to confidently state their case and support and defend their fundamental interests. This requires a) comprehensive knowledge of the issues and interests; b) the skill to strategically prepare with evidence and facts; c) an ability to articulate and persuade; and d) a nonadversarial focus and spirit.

Trump undoubtedly considers himself highly assertive. His breakfast broadside on Wednesday is proof. But he has undermined its effectiveness for years with his lack of preparation, spontaneous gut-level moves, threats, name-calling, an adversarial win-lose approach, and an extremely aggressive and often mean-spirited tone.

Putin, by contrast, appears to exhibit almost all these beneficial assertiveness characteristics—with the obvious exception of being nonadversarial, as Russia’s incursion in Ukraine and the well-documented meddling in the 2016 U.S. presidential election attest. Trump will have his hands full in Helsinki, not the least due to his lack of detailed knowledge of the issues.

Of course, Trump would point to his recent win with Pfizer—which agreed to temporarily roll back its price hikes this week—and his financial success over the years as evidence of his effective assertiveness. And he has negotiated some excellent deals in which his assertiveness played a positive role, including Trump Tower and his purchase of Mar-a-Lago. But his success with Pfizer and in those deals also reflected his aggressive exercise of leverage, a related but separate strategy based on his objective negotiating power.

The world’s best negotiators are also empathetic, as they deeply listen, understand and appreciate their counterparts’ needs and interests without necessarily agreeing with them. They have excellent questioning skills and intensely focus on their counterparts with open-mindedness and curiosity.

Mandela said, “I have always endeavored to listen to what each and every person in a discussion had to say before venturing my opinion.”

Few objective observers would describe Trump as an active listener, a deep questioner or someone who respects counterparts with whom he disagrees. Just ask Sen. John McCain, the former prisoner of war whom Trump ridiculed as not a hero; McCain later cast the deciding vote against Trump’s signature negotiation effort to repeal-and-replace Obamacare. Or ask former Mexican President Enrique Peña Nieto, who refused even to meet Trump shortly after his inauguration to negotiate over Trump’s signature campaign promise to build a wall on the Mexican border … and make Mexico pay for it.

Almost 50 years of Trump’s negotiating partners and counterparts would also weigh in here, including many of his erstwhile partners who became adversaries when he threw them under the bus after disagreements, including Harrah’s, numerous New York City development officials and his fellow United States Football League team owners.

“Personable, rational, perceptive, self-controlled, sociable and helpful” individuals, according to Schneider, exhibit high social intuition and emotional intelligence. Negotiation mastery requires these skills.

Trump has average skills here. According to many, he can be extremely charming when he turns on his “salesman” side. Unfortunately, he has combined these with Twitter rampages and an over-reliance on the value of personal relationships, whether with China’s Xi Jinping or North Korea’s Kim Jong -Un. Few concrete concessions from either tactic have been forthcoming. In fact, each illustrates the limitations of Trump’s overconfidence in his personal negotiation and relationship-building skills. After all, we’re now in a full-blown trade war with China. And North Korea recently derided the U.S. for its “gangster-like” behavior.

Of course, this is predictable. Personal relationships carry greater weight in business—where Trump has operated for many years—versus presidential negotiations—where Trump is a true neophyte.

Several Republican congressmen made this exact point during the health care negotiations, with Freedom Caucus leader Mark Meadows telling the Washington Post, “If this was about personalities, we’d already be at ‘yes’” after calling Trump “charming.” But, he then noted, “this is about policy, and we’re not going to make it about anything else.”

Rep. Dave Brat (R-Va.) told POLITICO much the same, noting after getting a call from Trump: “He’s selling. The salesman in sell mode. On that, he’s the best. Humor, heart, personality.” But Brat didn’t get his policy concerns addressed, so he didn’t support the bill.

Here’s the challenge relating to negotiation flexibility. Too much flexibility signals no core principles, no deal-breakers, no consistent strategy and weak leverage. Yet too much inflexibility signals no give-and-take, unnecessarily adversarial positional rigidity, a one-size-fits-all strategy and a weakening of parties’ credibility.

The right balance? Relative inflexibility on core issues and interests, with relative flexibility on more minor moves where it will satisfy the parties’ interests.

In this realm, Trump actually rates above average, at least early on in his business career. He was creative and appropriately flexible in several early deals when he dug into the details sufficiently to wheel and deal at the table. This led him to negotiate very effectively on his first big deal, the redevelopment of New York City’s Commodore Hotel. And he took a hard line on the major issues—but flexibly worked out the details—in his negotiations with financial institutions to stave off personal bankruptcy.

But later in business and once he ascended to the White House, his proficiency plummeted. As president, few counterparts have discerned core principles on which he won’t move. In fact, he has expressed support—on subsequent days, no less—of diametrically opposed positions on several major issues, including the Dreamers, gun control and health care.

Trade issues, though, are the closest thing Trump has to an abiding belief. He has opined about other countries taking advantage of the United States since the late 1980s. But he’s shown zero flexibility here (except in relatively minor one-off concessions, as with telecom manufacturer ZTE) and consistently misrepresents trade-related facts, undermining his effectiveness.

Trump’s well-documented reputation on issues of ethicality and honesty—ask the hundreds of subcontractors he stiffed despite their signed, valid contracts—undermines his negotiation effectiveness on all fronts. It doesn’t matter much what he says if his counterparts don’t believe him or feel he will renege the next day.

So how well will Trump negotiate with Putin on Monday? Putin scores relatively high on several of these characteristics, most notably his assertiveness, preparation and attention to detail, plus his inflexibility on core principles. Keep in mind, Putin has already accomplished some of his pre-negotiation goals—sowing discord within NATO, getting Trump to view Russia through a nonadversarial lens, and persuading Trump to openly consider weakening sanctions.