For Putin, relationship with influential Americans balances relations with China.
"Steve Witkoff, a billionaire real-estate developer and longtime golfing partner of Donald Trump, was just days into his job as the new president's special envoy to the Middle East when he received a tantalizing message from the crown prince of Saudi Arabia.
Vladimir Putin was interested in meeting Witkoff -- so interested that he might consider releasing an American prisoner to him. The invitation came from a Kremlin moneyman named Kirill Dmitriev, using the de facto Saudi ruler, Mohammed bin Salman, as an intermediary.
There was just one thing: Witkoff would be expected to come alone, without any CIA handlers, diplomats or even an interpreter, a person familiar with the outreach said.
The Russian president had been studying psychological profiles of the officials around Trump, including Keith Kellogg, the retired three-star general Trump had named as America's envoy to Russia and Ukraine. Putin's intelligence-agency reports stressed that Kellogg's daughter ran a charity in Ukraine -- a red flag signaling he might be hostile to Russian demands during coming peace talks, people familiar with the documents said. Kellogg had also shrugged off an appeal from television personality Tucker Carlson, who told him before Inauguration Day that Moscow was ready to start talking.
Perhaps there was someone else in Trump's inner circle who might make a better fit?
Ten months later, Kellogg is out and Witkoff and Dmitriev, two businessmen with strong personal connections to their respective presidents, are sketching a new economic and security order for Europe. Jared Kushner, Trump's son-in-law, has pitched in to help negotiate where Russia's borders will end, the shape of Ukraine's army and how quickly Trump could tear down the new Iron Curtain of sanctions for Russia's economy.
It is hard to pinpoint a moment in history when businessmen have held such direct sway over matters of conflict and peace. Since the end of World War II, Washington's relationship with Moscow was its most carefully calibrated, helmed by spy agencies who knew their rival intimately. Seasoned diplomats rehearsed rigid protocols to prevent misunderstandings between two nuclear powers poised like scorpions in a jar.
Today, those structures are virtually absent. America has had no ambassador in Moscow since June. There is no assistant secretary of state for European and Eurasian affairs. Witkoff has declined multiple offers from the CIA for a briefing on Russia. The State Department assigned a small group of staffers to support Witkoff, but members of that team, and others across the administration, have struggled to get summaries of Witkoff's foreign meetings.
Longtime allies in Europe also feel left in the dark, and worry that Washington no longer has their back, while Middle East monarchies are ascendant.
This month, Witkoff concluded his sixth trip to Russia, talking with Putin for five hours through midnight. Not since the U.S. allied with Joseph Stalin during the Lend Lease Act has a White House official enjoyed such frequent, personal access to a Russian or Soviet leader. Witkoff has yet to visit Ukraine. Its leaders -- and European capitals -- complain he is urging them to give Russia territory in return for a peace deal they aren't sure will hold. This weekend, Dmitriev is scheduled to visit Witkoff in Miami for another round of talks.
The emergence of Witkoff as envoy to the Kremlin is partly a story of Putin maneuvering to nudge aside America's diplomats and clasp hands with its billionaires. It wasn't a hard sell. Trump has made no secret of his skepticism about traditional institutions and alliances, valuing personal loyalty from a decadeslong friend like Witkoff.
As Kellogg sees it, Russia worked behind the scenes to replace him -- but it was Trump who made the call to narrow his portfolio to Ukraine. He and Witkoff get along well, he said in an interview. "I know the Ukrainians. He knows the Russians," he said. "Nobody's got their nose out of joint."
Speaking on Tuesday, Trump said that Witkoff "knew nothing" about Russia as he started the job, but was proving successful because "people love Steve."
To The Wall Street Journal, Witkoff, 68, calls himself a dealmaker. "It means putting yourself in the other party's shoes and figuring out how to help him get political space to do this deal," he said.
Yes, he lacks foreign policy experience, but nearly four years into a conflict that has cost more than a million casualties, he argues, it is time to try something new. Aware of the criticism that he is bumbling his way through diplomacy of the highest stakes, he stresses that he travels with diplomatic security and before trips, takes briefings by the National Security Council, Office of the Director of National Intelligence or Secretary of State Marco Rubio. After meeting Putin, he typically dials the president, vice president and Rubio over a secure U.S. Embassy line.
Presidencies from George H.W. Bush to Trump's first administration had numerous Kremlinologists and fluent Russian speakers, from Brent Scowcroft to Condoleezza Rice -- and yet none could head off a Ukraine crisis that has been building since the collapse of Communism.
"Perhaps in prior administrations you'd have a massively bureaucratic bloated process to get anything done," said White House spokeswoman Anna Kelly. "The president personally directs people he trusts, like Secretary Rubio, Special Envoy Witkoff and others, to implement his foreign-policy goals."
A White House official said that the decision to appoint Witkoff was Trump's decision alone. "Suggesting that foreign countries had any input on this is absurd," the official said.
Rubio in a statement said Witkoff is doing an "incredible job" and that he "understands the objectives and gets things done on behalf of the President and the American people."
To track the rise of business diplomacy, the Journal spoke to current and former U.S., Russian, European and Arab officials and businessmen, several of whom have been in the room during negotiations with Witkoff. In a series of interviews, Witkoff and Dmitriev described the evolution of their partnership.
"Trump thinks like a businessman, he thinks deals, but Putin thinks 100% the opposite," said Boris Bondarev, a former senior Russian diplomat who fled shortly after the Ukraine invasion and now lives in hiding. "For Putin, the conflict is more than a worldly matter, it's something sacred, something he must do, and that's why he sees Trump as a very good guy."
An early riser, Witkoff begins his day as it ends, pacing with his cellphone on a video call, its camera jerking haphazardly around the interior of his waterfront Miami mansion or private jet. The unlikely diplomat trying to end Europe's bloodiest war since 1945 speaks in golfing metaphors and long asides about the nature of capital markets.
The Bronx-born billionaire travels to Russia on his own private jet, paying his own expenses, a White House official said.
On some foreign trips, he brings his girlfriend Lauren Olaya, a former golf pro and anchor on Fox's "Swing Clinic," the official said. She doesn't join him in official meetings.
Witkoff said he has his own, tight-knit team within the government: "We develop a thesis on how to be successful," he said. "So I don't need to travel around with a zillion people."
He rarely visits the State Department, which prepared for him one of its most historic offices: the high-ceiling, wood-paneled suite where Secretary of State George C. Marshall planned the reconstruction of Europe. He prefers first daughter Ivanka Trump's old desk in the West Wing.
He likes to tell skeptical Ukrainians that once they settle, he could unlock $800 billion in reconstruction money -- a flood of investments four times the Marshall plan -- according to European officials who have been in the room with him. It is the kind of boastful big numbers, mixed with a make-money-not-war philosophy, that has endeared him to his boss, a friend of four decades.
After Trump's 2020 loss, Witkoff testified as a character witness during a Manhattan fraud trial when many previous supporters and donors were shying away.
He traveled with Trump throughout his second campaign and was golfing with him the afternoon a Secret Service agent found a pro-Ukrainian would-be assassin aiming his rifle near the sixth hole.
In one of his first appointments upon winning re-election, Trump named his friend as Middle East envoy.
Witkoff had previously done business with some of the Arab world's most powerful royal families. He co-owned the Park Lane Hotel in New York with an Abu Dhabi sovereign-wealth fund for a period, and has a close relationship with Qatar's prime minister, Sheikh Mohammed bin Abdulrahman al-Thani.
The dealmaker didn't waste any time working the phones. In the interregnum between Trump's election and inauguration, Witkoff joined forces with the outgoing Biden administration to negotiate with Israel and Hamas over a cease-fire in Gaza.
He was also dialing Gulf power brokers over Houthi attacks on ships bound for the Suez Canal and cursing at Prime Minister Benjamin Netanyahu.
The Trump team was in close contact with the Biden White House about which foreign officials they were speaking to, former officials said.
But Russia was especially delicate. Some incoming Trump national security officials tried to understand how to start a dialogue with the Kremlin without triggering an investigation, as Trump's former national security adviser, Michael Flynn, had in 2017.
Trump's official Russia envoy, Kellogg, held back. In the weeks before the inauguration, Carlson encouraged him to speak with the Russians, but Kellogg -- who had served as national security adviser to Vice President Mike Pence and later as a Fox News contributor -- wanted to hold off. Carlson disagreed: "He was totally committed to conflict with Russia," he said in a text message to the Journal.
Kellogg told the Journal that was "bullshit." From the moment Trump appointed him, he said, "I began working aggressively to achieve his goal of ending the death and destruction."
As it turned out, an official from the Kremlin, known as "Putin's money man," was already talking to the crown prince of Saudi Arabia about another envoy from the Trump administration: Steve Witkoff.
Last December, while Witkoff was visiting Saudi Arabia to discuss Gaza and other issues, the crown prince made an offer: I can help you solve Ukraine.
It involved Prince Mohammed's longtime friend and the head of Russia's sovereign-wealth fund, Kirill Dmitriev, whose wife is good friends with Putin's second daughter.
A bespectacled 50-year-old Harvard and Stanford alum, Dmitriev spoke the language of Wall Street. The Ukraine-born Russian citizen had moved to Moscow after Putin's 2000 election, helping usher in a flood of foreign capital in the heyday when his former employer, Goldman Sachs, spoke of Russia as one of the world's top investment opportunities.
When foreign investment tanked after Putin re-united Crimea, Dmitriev stepped up efforts to tap the Middle East. He befriended the region's most powerful royals, including Prince Mohammed, who in 2015 pledged to invest $10 billion in Russia's economy.
In 2020, the fund manager helped Kushner coordinate Russia's support for U.S. priorities in the Middle East. That included salvaging an oil alliance known as OPEC+, and the so-called Abraham Accords to normalize Israeli-Arab relations. Kushner would later see those initiatives as a model for what he and Witkoff could arrange between Russia and Ukraine.
While Witkoff was in Saudi Arabia, Prince Mohammed offered to make an introduction to the Russians, according to people familiar with the discussions.
In January, Witkoff began telling people that he might be asked to take on the Iran and Russia portfolios. A White House official said he began communicating with Dmitriev soon after the inauguration.
Dmitriev asked Prince Mohammed to deliver a message to Witkoff. Putin wanted to talk to the new Middle East envoy, and there was a deal to be done: Russia might be willing to negotiate a prisoner exchange as a gesture of good faith.
The prisoner in question was Marc Fogel, a high school history teacher serving a 14-year sentence in Rybinsk penal colony for carrying cannabis into Moscow's Sheremetyevo airport.
In an Oval Office meeting in the first weeks of the administration, Kellogg briefed the president and others on a plan to tackle the conflict in Ukraine. "You take Ukraine," Trump told him. "I've got Russia." Witkoff wasn't in the room.
Days later, Kellogg got a message from a colleague on the National Security Council: Witkoff had received security clearance for a Moscow trip.
On Feb. 11, Dmitriev met Witkoff at the airport and reassured him as they raced toward the Kremlin in a government car.
For three hours, Putin hosted Witkoff, who took notes as the president gave a lecture on the 1,000-year history of Russia.
Putin was assessing whether the man in front of him was as open to the Russian perspective as his profile suggested, two people with knowledge of the meeting said. If so, a gift had been prepared for him to take home. Fogel had been transported more than four hours to Moscow by the FSB, not told where or why he was moving.
Witkoff's heart skipped a beat when he saw Fogel waiting for him at the Moscow airport. He watched, tears in his eyes, as Fogel called his mother, nearly the same age as his own, as they flew home through a February snowstorm, Fogel recalled. Russia was very accommodating, in Witkoff's view.
Trump spent two hours with Fogel, patting him on the back and touring the Lincoln bedroom as the freed man gushed thanks to "Steve." Trump, visibly moved, said he wanted to bring home as many Americans as possible from Russian jails. (The U.S. released the Russian co-founder of a bitcoin exchange from its custody the next day.)
His Middle East envoy, who he called "a killer" dealmaker, would become America's emissary to the court of Putin.” [1]
1. Putin Backed Witkoff In His Unlikely Diplomatic Ascent --- Release of American prisoner, Saudi foray bolstered Trump's 'dealmaker'. Parkinson, Joe; Ballhaus, Rebecca; Hinshaw, Drew; Grove, Thomas; Faucon, Benoit; et al. Wall Street Journal, Eastern edition; New York, N.Y.. 20 Dec 2025: A1.
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