U.S. President Donald Trump has tasked one of his closest friends with traveling to Russia this week to meet with President Vladimir Putin. He wants to unblock negotiations on a peace agreement for Ukraine, which seemed close a few days ago but has stalled again due to Moscow’s indifference. And for that, he needs someone he can trust. His emissary is Steve Witkoff, a 68-year-old New Yorker born into a Jewish family in the Bronx who has no background in diplomacy — and yet has been performing this critical task for several months now.
Witkoff, the son of a ladies’ coat manufacturer, has recounted on several occasions how that friendship began. In 1986, he was working as a junior lawyer for a law firm advising on a real estate transaction involving the Trump family. At that time, the current president had not yet founded his own company. The negotiations dragged on all night. During a break, almost at dawn, Witkoff went down to a deli to grab a bite. There he ran into Trump, who had ordered a ham and Swiss cheese sandwich but didn’t have the money to buy it because he had forgotten his wallet. Witkoff offered to pay for him.
They didn’t see each other again for eight years. But in 1994, when Trump was already a public figure, they met and reminisced about the sandwich incident. From that moment on, they became inseparable friends. Both are New Yorkers, both are millionaires, both amassed their fortunes as real estate tycoons, both moved to Florida with their families, and both are passionate about playing golf. In fact, Witkoff was with Trump at the West Palm Beach course in Florida when the second assassination attempt against the then-Republican candidate took place there in September 2014.
Witkoff will travel to Moscow this week amid an ongoing controversy surrounding the leak of a phone conversation he had with a Putin advisor, in which Trump’s envoy offered advice to the Russians on negotiating with the U.S. president. The leak of the call, published by Bloomberg, has generated unease and misgivings among Ukrainian negotiators, European partners, and even some Republicans in Congress, who believe the U.S.-proposed peace plan for Ukraine is being designed at Moscow’s behest.
The phone call took place on October 14. The transcript shows Witkoff speaking with Yuri Ushakov, Putin’s top foreign policy advisor, and alluding to the draft peace plan for Ukraine, which points to the need for Kyiv to accept the loss of territory to Russia. “From me to you, I know what it will take to achieve a peace agreement: Donetsk and maybe a land swap somewhere. But I’m saying that instead of talking like that, let’s talk with more hope because I think we’re going to reach an agreement here. And I believe, Yuri that the president will give me a lot of space and discretion to reach the agreement,“ the American envoy told his Russian counterpart.
Furthermore, Witkoff advises Ushakov that the Russian president should shower the American with praise and emphasize his peacemaking qualities as a way to win him over. He even urges him to arrange a conversation between Putin and Trump before Ukrainian President Volodymyr Zelenskiy is due to arrive at the White House for an official visit during which the latter Zelenskiy was expected to request long-range missiles from Washington that could potentially tip the scales of the war in Ukraine’s favor. The call between Putin and Trump did indeed take place the day before Zelenskiy’s visit, and the U.S. president ultimately denied Kyiv the missiles and pressured the Ukrainian leader to yield to Russian demands.
Ukraine’s diplomatic offensive, along with its European allies, has softened the U.S.’s 28-point peace plan, toning down its initial pro-Russian slant. But the move has not pleased the Kremlin, which has frozen negotiations. “There was no peace plan, there was a list of issues that were proposed for discussion,” Putin declared on Thursday. “Every word of the peace plan for Ukraine must be seriously debated,” he added.
So Witkoff, a generous donor to Trump’s presidential campaign, will have an important mission next week if he manages to meet with Putin. It won’t be their first meeting. The real estate mogul has an estimated fortune of $2 billion, with a portfolio of buildings, hotels, and other properties in New York, Los Angeles, and Florida, and businesses in Arab countries. In February, following intervention by Saudi Crown Prince Mohammed bin Salman, he traveled to Moscow to negotiate directly with Putin during a three-and-a-half-hour meeting for the release of an American teacher, Marc Fogel, who had spent three years in a Russian prison accused of marijuana smuggling. In exchange, the United States released a Russian cryptocurrency kingpin. In early August, he met again with the Russian president to prepare a meeting with Trump in Alaska.
Although he is currently negotiating peace in Ukraine, Witkoff’s official title is Special Envoy for the Middle East. Republican Senator Lindsey Graham of South Carolina revealed in an NBC News interview that Witkoff offered his services to Trump to negotiate peace between Israel and Palestine. “Trump looked at me and said, ‘Well, a million people have tried. Let’s pick a nice guy who’s a smart guy,’” Graham recounted.
Months later, Witkoff and Jared Kushner, Trump’s son-in-law, became the architects of the peace plan and the subsequent negotiations that ended with the agreement between Israel and Hamas in Gaza, after two years of war that left more than 67,000 Palestinians dead, many of them children.
Witkoff, who is unfamiliar with the intricacies of diplomacy but knows the tricks of business deals inside and out, brought that agreement to fruition after 10 frantic days of calls and multi-party meetings between Israeli officials and leaders of Arab countries. He secured the release of the Israeli hostages by the Palestinians and the freedom of some 2,000 Palestinian prisoners from Tel Aviv.
Before that, Trump had already turned to his friend immediately after winning the election. In November 2014, he sent Witkoff to the Middle East to negotiate a ceasefire. Since the change of government had not yet taken place, the New Yorker had to work with Joe Biden’s team. Some members of that team have fond memories of Witkoff’s role.
Just before the election, the U.S. president had also asked his friend to smooth things over with his Republican rivals. The party primaries had been fiercely contested, and Trump had left some wounds in his wake. Witkoff lent his private plane to facilitate a meeting between the president and Ron DeSantis, the governor of Florida. He also facilitated reconciliation with the governor of Georgia, Brian Kemp, and the former ambassador to the United Nations, Nikki Haley.
The truth is, these two real estate moguls have a long history together. After all, Witkoff is still the man who buys Trump sandwiches and solves his problems.
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