THE ART OF THE (HOLLOW) DEAL

Why Trump’s Negotiation Style Fails the Win-Win Test 

By Mark Young

President, Rational Games, Inc. 

1 June 2025

“Deals are my art form,” Donald Trump boasts in The Art of the Deal. “I am quite simply a brilliant dealmaker.”

It’s a bold claim and one that may appear credible at first glance. Trump exudes confidence, commands media attention with flair, and barrels forward with relentless energy. Witness his recent whirlwind involvement with crises from Gaza to Capitol Hill, all in a week. The performance is dazzling.

Yet negotiation, as we teach it at Rational Games, is not a performance.

It’s not about dominating a room, bullying a counterpart, or claiming a quick win. True negotiation is about creating lasting value, understanding the interests underlying the positions, and building relationships founded on trust, empathy, and cooperation. Judged by those standards, the “art” in Trump’s deals reveals itself as dangerously hollow.

Let’s examine the cracks in this gilded façade. The Pitfalls of the Trumpian Playbook:

1. Disregard for Process and Preparation: Trump’s notorious impatience and distaste for detail undermine sustainable outcomes. Negotiation demands curiosity, preparation, and an attention span longer than the next news cycle.

2. Disruption Without Reconstruction: Breaking norms may energize, but without vision or empathy to rebuild, the chaos is costly. At Rational Games, we believe in disrupting to transform, not just to destroy.

3. A Business Lens on Every Conflict: Not every dispute is transactional. Strategic framing matters. Conflict zones like Ukraine or the Middle East are not business ventures; they are moral, historical, and deeply human. Attempting to monetize them cheapens the complexity and sabotages trust.

4. Relational Myopia: Deals don’t end at the signature. In real life, you meet again. Win-win negotiators preserve the relationship, knowing it’s often more valuable than the agreement itself.

5. Zero-Sum Thinking: Trump’s inability to look beyond his gain closes the door to joint value creation. At Rational Games, we teach that the pie can and should be made bigger.

6. Short-Term Wins, Long-Term Damage: Flashy gains often come at the expense of tomorrow’s credibility. Great negotiators play the long game, building reputational capital with every interaction.

And in terms of classic negotiation mistakes:

7. Weak Anchors and Quick Concessions: Trump often starts strong but folds under pressure. An effective negotiator knows how to make and defend a principled offer and how to say no with dignity.

8. One-Note Style: Bluster. When all you have is a hammer, every problem looks like a nail. Trump’s bullying may work in reality TV, but at the global table, it closes ears and opens resistance.

9. Manufactured Time Pressure: Deadlines and ultimatums rarely foster better deals. They create anxiety, not alignment.

10. Truthful Hyperbole: The Ethics Void Trump's Comfort with Exaggeration Undermines the Core of What We Believe: That Negotiation Is Not Just About Results, but About How You Get Them.

At Rational Games, we hold that negotiation is not merely a tool for striking bargains, it’s a path to creating peace, resolving conflict, and building better systems. A good negotiator seeks sustainable outcomes and stands for something.

We train not in tactics of dominance, but in the art of listening, building, and creating value through games, play, and grounded theory from thinkers like Roger Fisher, William Ury, and Daniel Shapiro.

We aim to make negotiation a human, empathetic, and principled practice. Trump’s approach might get the spotlight, but it rarely gets the substance or the sustainability.

So let’s ask ourselves: What kind of negotiation culture do we want to model?

At Rational Games, we believe the future lies in cooperation, not coercion. In creativity, not chaos. In win-win, not hollow wins.

Let’s play a better game.

Comments welcome.