In the mid-80s, Donald Trump, a billionaire and a celebrity, told anyone who would listen that he could end the Cold War in a day. He believed that all it took (and he was lobbying for it) was for President Ronald Reagan, his friend Ronnie, to appoint him as a plenipotentiary ambassador, and with his unique negotiating talent, he would sit the Russians down at the table and sign an agreement. 40 years later, Trump is president for the second time and still sees the world exactly the same way. He admires the powerful, authoritarian figures, and those he considers winners. He despises losers, those who "don't have the cards" to play a significant role. And above all, he believes that he, his friends, and his family are the only ones qualified to solve the world's problems. Not diplomats, not conventional politicians, not experts: businessmen, those who understand the "art of the deal."
This explains the power of Steve Witkoff, a 68-year-old amateur with a fortune of over 2 billion dollars and conflicts of interest everywhere. He is the special envoy for the Middle East and whatever else comes up. A man with no training or experience in foreign policy who has already met with Vladimir Putin three times and has been seduced by his rhetoric; the one who pressured Benjamin Netanyahu, the one who mediates between Arab leaders and terrorist groups. The United States has historically promoted businessmen, lawyers, and figures who transitioned from the private or academic sector to key positions in its foreign policy. Especially as ambassadors and special envoys, but also as ministers. Trump almost exclusively trusts them. That's why he appointed executives like Rex Tillerson or Mike Pompeo as secretaries of State and put others like Mark Esper in charge of Defense. But this case is special.
Marco Rubio is, on paper, responsible for American diplomacy, but in the capitals of Europe and Asia, it has been understood that to truly reach the president's ear, it is often better to court Witkoff, a real estate magnate considered by some as the shadow Secretary of State. Because Rubio holds the position, but he also has a history as a Trump rival, someone who insulted and disrespected him. Witkoff, on the other hand, has been a friend for over 40 years, a golfing buddy (he was playing with him the day a man armed with a rifle and hiding in the bushes was arrested a few hundred meters away from them), someone whom Trump appreciates, respects, and who has no political ambitions.
Witkoff, like Trump, is a New Yorker. He was born in the Bronx and raised on Long Island in a Jewish family that manufactured coats for women. He studied Law and Political Science and bonded with the current president one early morning in 1986 during marathon negotiations for a real estate deal. Witkoff, a partner at the Dreyer & Traub law firm representing the magnate, went to get food at a 24-hour establishment on East 39th Street and rescued a hungry, cashless Trump. "I asked for a ham and Swiss cheese sandwich," he explained two years ago in court when he testified in favor of his friend in one of Trump's fraud trials. The snack laid the foundation for their subsequent friendship.
Trump convinced Witkoff to specialize in real estate law and transition to development. In the 90s, he founded his company, the Witkoff Group, which owns several properties in New York, including the Park Lane Hotel and the Woolworth Building. Like Trump, he has close family members leading the businesses, including his ex-wife, Lauren Rappoport, and his sons Zach and Alex, who is the co-CEO. They also have controversial cryptocurrency businesses in common with the president's children.
His personal bond with the president is very strong, in both directions. In July 2024, at the Republican National Convention, he said he had the "privilege" of calling Trump a "true and dear friend for many years, through good and bad times," such as the death of one of his sons from an overdose in 2011. Witkoff is unwaveringly loyal, completely loyal, and stood by his side through divorces, bankruptcies, trials, and, above all, did not turn away after the Capitol riot and what seemed like his downfall. That's why Trump treats him almost like family. "A person like Donald Trump has many acquaintances, too many to even name or count. He has very few true friends outside his family, and Steve is primus inter pares among them," said Susie Wiles, the powerful White House chief of staff.
Witkoff has served his leader in Moscow, Tel Aviv, or Doha, as well as in negotiations with the Republican rivals whom Trump defeated in the party primaries. At a post-election dinner in November 2024, he unexpectedly put himself forward as a possible presidential envoy to the Middle East, citing his ties to the region (in reality, with the Gulf countries' sovereign funds, which rescued him in the past from failed business operations). It was the same position his son-in-law, Jared Kushner, held in the Republican's first term. "And Trump looked at me and said, 'Well, a million people have tried. Let's choose a good guy who is smart,'" the businessman recounted.
His style is clearly more discreet. He doesn't raise his voice, but his language is very similar to Trump's: with clear objectives, grand promises, and the same excess of confidence. He doesn't speak other languages, has no experience in foreign policy, or basic diplomatic training. He doesn't grasp the codes, nuances, and sensitivities. He doesn't understand the culture, history, and traditions of the governments or organizations he has to deal with. And he doesn't seem to believe that it matters.
In interviews and podcasts, he has stated that for peace negotiations, he follows his instincts, relies on his intuition and his track record of success in real estate deals. And, above all, he uses his personal relationship and access to the president as an asset. Since January, he has explained that he "has read many books and watched Netflix documentaries on global conflicts," and has come to the conclusion that being an outsider, someone detached from the past and therefore less cynical and pessimistic, is the best asset, and that "he can leverage the lack of experience and succeed where professionals have failed." Just like Trump in politics.
The reality is very different. He is an amateur who often fails to grasp the gravity of situations, simplifies and trivializes dramatically, relies on falsehoods (especially in the case of eastern Ukraine), and focuses on achieving results he can boast about, regardless of the consequences or victims. He uses private and unencrypted mobile phones with absolute irresponsibility for calls or messages in exposed messaging groups. He works with a very small team, about half a dozen people, who do not charge for their work and he often pays for their travel on his private plane. A "lone rider," disorganized, constantly improvising, with offices halfway between the White House and the State Department. Accompanied on his trips by his girlfriend, Lauren Olaya, a former professional golfer.
Being accountable only to the leader, with almost absolute autonomy. And with overwhelming conflicts of interest. Years ago, Witkoff got caught up in a scandal with a Malaysian fraudster, a hotel he couldn't sell, and banks pressuring him to repay the loan he had used to buy it. He moved with Arab funds and, in the end, the one from Qatar, interested in his ties to Trump, came to the rescue. Now, a decade later, his son Alex has been getting money from the same Gulf actors with whom his father was negotiating peace in the region.
Putin has mocked him time and time again. He makes him wait for hours when he goes to Moscow, tells him what he wants to hear, and his advisors have created a strong and effective bond. After each trip, Witkoff returns to Washington embracing the Kremlin's proposals, openly stating in front of the cameras how much he respects and trusts Putin. And privately advises (as seen in the leaked call last week) the Russians on the best way to seduce the President of the United States. "I like Putin, he's not a bad guy", he said, delighted, to Tucker Carlson, another friend of Trump seduced by the Russian leader and blinded by his privileged access.
"I think Mr. Witkoff has adopted the Russian side's strategy. I think it's very dangerous because, consciously or unconsciously, I don't know, he is spreading Russian narratives," lamented Volodimir Zelenski in the spring. Not by chance, he does not go to Kiev nor allows Marco Rubio to go to Moscow. Only him or, as on this occasion, Trump's son-in-law. Those who see business opportunities everywhere, from the Gaza Strip as a new Riviera to Russian commodities.
Witkoff is the closest thing to a realist in International Relations, someone who thinks and acts in terms of interest defined as power, but ignoring decades, if not centuries, of wars, hatred, and passions. Someone who believes that if there are no agreements, it's not because of what's at stake, but due to the lack of talent or creativity of those in charge. "I'm not an ideologue, I'm an amateur diplomat. But diplomacy is negotiation, and I've been doing it all my life", he told a journalist from The Atlantic before the summer.