Personal business ties and loyalty are Trump’s yardstick for naming diplomats
TEHRAN – President Trump has consistently favored real estate developers, major business executives, and corporate negotiators for high-profile diplomatic and envoy positions.
In his first administration, roughly 43.5% of his ambassadorial appointments were political appointees rather than career diplomats—a historical high—with a heavy concentration of business magnates. That trend has leaned even further into utilizing personal business relationships for sensitive geopolitical assignments.
He has tasked high-profile real estate developers and business figures to deal with critical diplomatic and negotiating tasks.
Among these negotiators and diplomats are Steve Witkoff, Jared Kushner, Thomas Barrack, etc.
Witkoff, a real estate developer, is one of Trump's most prominent diplomatic appointments. He is a billionaire New York property developer (founder of the Witkoff Group) with no prior foreign policy experience. He was appointed Special Envoy to the Middle East and Special Envoy for Peace Missions.
Jared Kushner, also a real estate developer, served as Trump’s senior advisor and de facto special envoy during his first presidential term.
Kushner, who is also Trump’s son-in-law, and Witkoff have been acting miserably as Trump’s chief negotiators to put an end to the Ukraine war.
Witkoff’s diplomatic performance in the Ukraine conflict has been widely criticized as incompetent, largely due to his lack of regional expertise and his go-it-alone negotiation style.
Writing in MS Now in September 2025, Steve Benen said, “When it came time for Donald Trump to choose a special envoy to work on ending Russia’s war in Ukraine, the president had a small army of experienced, knowledgeable and qualified diplomats to choose from. The Republican tapped Steve Witkoff for the job instead.”
Witkoff effectively admitted as much to Tucker Carlson during an interview in March. “I underestimated the complications in the job, that’s for sure,” he said. “I think I was a little bit quixotic in the way that I thought about it. Like, I’m going to roll in there on a white horse. And no, it was anything but that, you know.”
In August 2025, Politico wrote, “Some frustrated U.S., Ukrainian and European officials say part of the problem is the go-it-alone style of Witkoff, Trump’s special envoy for peace missions and go-to negotiator on Ukraine. He has refused to consult with experts and allies, leaving him uninformed at times and unprepared at others, according to seven people familiar with internal discussions. Two said he misses the mark by viewing the conflict through a real estate lens, like a land dispute.”
Multiple reports have indicated Witkoff acted as a parallel Secretary of State, frequently failing to consult with seasoned diplomats and State Department experts.
Witkoff’s diplomatic negotiations with Ian have proven catastrophic.
Prior to the U.S. air strikes on three Iran’s nuclear sites – Fordo, Natanz and Isfahan - with B-2 bombers in June 2025, Witkoff held two rounds of talks with Iranian Foreign Minister Abbas Araghchi. The first round was held on April 12 in Muscat and the second round on April 19. The two rounds were mediated by Oman.
Witkoff and his master suffered and still continue to suffer from the illusion that complicated issues can be resolved easily and in a short time.
After the June conflict, known as the 12-day war, Iran agreed to hold talks again with the U.S. side upon insistence by friendly countries and a willingness by Tehran not to shut the door to diplomacy. Anyhow, the talks were resumed in early February. This time, Kushner joined Witkoff. They formally met on February 6 and February 26. Though Omani Foreign Minister Badr Al Busaidi as a mediator, wrote on X that the sides made "substantial progress" on a potential nuclear framework, the U.S. and Israel suddenly started a war of aggression against Iran to the surprise of the world on February 28.
Another incompetent Trump diplomat is Thomas Barrack, a real estate investor. Trump nominated Barrack, his longtime friend and property mogul, to serve as ambassador to Turkey.
Middle East Eye reported on May 31 that Barrack would also serve as Trump’s special envoy to both Syria and Iraq.
Before being named special envoy to these two countries, he made frequent visits to Beirut after the ceasefire between Lebanon and Israel in November 2024. However, his trips produced no results. He only tried to deepen divisions between the rival Lebanese political factions that helped Israel to continue violating the ceasefire. The violation of the ceasefire continued until the war broke out on March 2, 2026, following the U.S.-Israel war on Iran.
Barrack is notoriously famous for his reckless remarks when talking to reporters at the presidential palace in Baabda, Beirut, on August 26, 2025, when he used the word “animalistic” as reporters, like anywhere else in the world, competed to ask their questions. He told them: "Act civilized, act kind, act tolerant... The moment that this starts becoming chaotic, like animalistic, we're gone."
Trump’s ambassador to the European Union, Gordon Sondland, also a hotel developer, marked the beginning of the emergence of a rift between the Trump administration and the EU, especially after Trump scuttled the 2015 Iran nuclear deal despite warnings by European leaders.
Sondland bypassed traditional State Department channels to act as a direct negotiator on trade and Eastern European policy.
Using real estate developers as diplomats and envoys represents a distinct approach to international relations in Trump’s administration. Rather than relying on standard diplomatic protocols, these appointments leverage transactional, high-stakes corporate negotiation tactics. This strategy frequently places personal loyalty and private-sector bargaining experience directly at the center of Trump’s foreign policy.
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