The US — Iran Negotiator, Steve Witkoff’s Psychological Profile. An Unfit Choice.
Steve Witkoff is U.S. President Donald Trump’s Special Envoy to the Middle East. Witkoff’s political position is unusual: his November 2024 appointment rests entirely on his longstanding personal relationship with Trump rather than prior diplomatic accomplishments. Witkoff is Trump’s golf partner, business associate, and Mar-a-Lago club member.
For decades, Witkoff worked in real estate development, where negotiating success depends on personal relationships, identifying mutual interests, and reaching compromises where everyone makes money. This experience frames how Witkoff has approached international conflicts and Middle East relations. The problem is that international relations differ from commercial real estate negotiations, where both sides seek financial profit.
In his failed negotiations with Iran, Witkoff was ill-equipped to negotiate with a partner seeking expanded territorial control, greater political influence, and weakened US influence in the Middle East. Iran’s objectives were alien to Witkoff, whose entire repertoire of negotiating skills was honed while developing luxury hotels, golf courses, and apartment buildings. Only after meeting with Iran’s representatives did Witkoff learn that they don’t play golf in Iran.
Witkoff’s failure as an international negotiator stems from the delusions that he and Donald Trump share. Both men approached negotiating with Iran like they were building a hotel. Neither anticipated the problems they would encounter because neither could imagine waters deeper than an estate deal. Saying that Trump and Witkoff misjudged Iran is a charitable understatement.
For its part, Iran has played like a grandmaster playing chess against a novice. Trump and Witkoff still haven’t figured out that Iran always had all the cards, and they were being played.
Iran’s objective has always been to expand its sphere of influence, and it has done just that. Aside from making Trump look like a fool, Iran’s resolve has highlighted the US’ trillion-dollar military impotence and lack of leadership. The truth of the matter is there’s zero credibility associated with appointing a kiss ass real estate developer pal of Donald Trump’s as the US Middle East Envoy.
Trump and Witkoff’s business experience has almost entirely been based on cultivating a US “good ole boy” network. That strategy has not translated into successful foreign policy. In fact, the US Middle East policy under Trump has been a catastrophic failure on all levels. For example, Israel’s destruction of Gaza with weapons the US supplied violated the established rules of war. As a consequence, the International Criminal Court indicted Israeli Prime Minister Benjamin Natanyhu for genocide and crimes against humanity. The complicity of the US in the Gaza genocide raises conflict of interest questions about Steve Witkoff. Witkoff is Jewish and supports Israel. Is that the guy you would want negotiating with Iran?
Witkoff and Trump’s relationship-based negotiating style was a non-starter in the Iran negotiations because both men are friends with Israel’s Prime Minister, and Israel was bombing Iran. When Iran expressed its unwillingness to meet with Witkoff, he and Trump erroneously concluded that Iran didn’t have a desire for peace. The global risk posed by Witkoff’s psychological profile is that he sees Iran’s lack of friendliness toward him as a personal affront. In Witkoff’s eyes, Iran is like the banker who refuses to loan his real estate company money.
In real estate deals, protracted negotiations create tension. This psychological stressor occurs when someone has invested significant money and time in a real estate project, and the project is delayed. Delays increase interest expenses, disrupt construction schedules, and in general make the project less profitable.
Drawing on their real estate experience, Trump and Witkoff subconsciously compared Iran’s foot-dragging to a delayed real estate deal, and they walked away. Now, instead of admitting Witkoff’s personal failure as a diplomat, Trump is threatening to use the US military to annihilate Iran and its people. Trump’s stated plan to kill Iranian civilians based on their nationality, if carried out, will be the same as the genocide Benjamin Netanyahu committed when he killed hundreds of thousands in Gaza because they were Palestinian.
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Trump and Witkoff have approached diplomacy with Iran, and many other countries, like they were building a hotel. Their real estate development approach may have worked in New York City, but that’s small potatoes compared to Iran, which has 93 million people. When Trump and Witkoff’s “let’s make a deal” strategy flopped, they tried to extract unilateral concessions by using military force.
Eight months have passed since the US war against Iran began, and it has caused the US to lose enormous respect in the world community. Even more humiliating than the ongoing decline of US prestige is that the US coalition with Persian Gulf nations is in tatters. All of the US allies in the Gulf have been under constant attack and suffered enormous damage because the US can’t or won’t defend its Gulf state partners.
An immediate consequence of Trump and Witkoff’s diplomatic bumbling is that Saudi Arabia is now on the verge of collapsing as a state. Witkoff’s commercial real estate bargaining skills have been a bust in the Middle East. They did work in Israel, however, where he and Trump’s son-in-law have proposed (Project Sunrise) a $112 billion oceanfront hotel and casino development in Gaza.
The Persian Gulf states pose a different set of circumstances than Gaza, but the outcome could be the same. The widening Persian Gulf war and destruction are slowly unraveling the fabric that holds those states together. Times are so tough that this week, the Saudi-funded and Trump-backed LIV professional golf league filed for bankruptcy. Maybe Steve Witkoff, with his access to super-secret classified information, can tell us which grifter convinced the sand kingdom (Saudi Arabia) to invest in golf.
Before it’s too late, the Saudis and other Gulf states must acknowledge that the US screwed them over and doesn’t have their back. A wise decision would be for them to immediately freeze all US military activities for 60 days and ask Iran and the Houthis to do the same. Then start negotiating based on what you all have in common.
Persian Gulf peace negotiations could be aided if the participants paused to reflect on where they came from. Look back 4,500 years and think about the Middle Eastern ancestors who built the Great Pyramid and traded with the Gulf states and Persia. All the peoples fighting each other in the Gulf have some Egyptian in them.
Egyptians laid the foundation for civilization, and the pyramids show who the world’s true leaders were. The pyramid builders' leadership has stood the test of time, and those in the Middle East waging war against each other are not living up to the potential their ancestors bestowed.
It pains me to say that “The Gulf state fighting has brought shame on their ancient ancestors to whom we owe so much. Stop all US military activities in Gulf nations, and don’t invite Trump or Witkoff to your peace negotiations. If you get stuck, I would recommend 2026 Nobel Peace Prize Winner Navi Pillay as an arbitrator. She was responsible for Benjamin Netanyahu being indicted for genocide. She is honest, speaks the truth, and is empathetic.
Eight months since the US — Iran war began, three things are clear:
1) The US has huge debt problems domestically and can’t afford the cost of adequately defending its Gulf state allies. Trump’s America First policy does not include Persian Gulf nations. The US has made promises it can not keep.
2.) Low-cost off-the-shelf weapons technology has made high-cost US military hardware and defense systems obsolete. The Ukraine’s asymmetric warfare strategy is defeating Russia, and Iran is using the same strategy in the Middle East. Persian Gulf nations have spent hundreds of billions of dollars on US weapons that are not keeping them safe.
3. ) The war against Iran is like a cancer. It’s slowly eating away at all of the Persian Gulf nations. There is no end in sight because the US has suffered no adverse consequences. When the war does end, trillions of dollars in Persian Gulf damage and lost resources will have occurred. There will be no winners.
