Steve Witkoff’s record should worry us all

The man tasked with negotiating world peace is an old friend and golfing partner of Donald Trump. But when it comes to the most sensitive negotiations on earth, he is in desperately over his head

March 28, 2025

So, Steve Witkoff, the Henry Kissinger of our age. What do we know about this man charged with simultaneously bringing peace to the Middle East; creating harmony between Russia and Ukraine, and forging a love-in with Iran?

The routine profiles tell us little about the 68-year-old Bronx-born property developer beyond the fact that he was in the same line of work as Donald Trump and that the two men played a lot of golf together. But Trump clearly believes his golfing chum has exceptional negotiation skills. Why else would he pick him to shuttle between Vladimir Putin, Hamas, and Bibi Netanyahu in a bid to solve everything all at once?

Kissinger had been a US Army intelligence officer in the Second World War. At Harvard, he developed an intense knowledge of foreign policy and was a leading expert in arms control and disarmament. By the time he became National Security Advisor, he was “one of the most important theorists about foreign policy ever to be produced by the United States,” according to his biographer, Niall Ferguson.

Steve Witkoff develops luxury hotels.

Sure, that involves negotiations, a calm head, and good judgement. But you can be sure that the KGB will have assembled a much deeper profile of the man who has already met with Putin twice.

So far, things are going swimmingly, with the newly appointed US envoy describing the Russian president as “a super smart guy… I don’t regard Putin as a bad guy… I liked him… I thought he was straight up with me.”

So, he’s a great judge of character.

What would our KGB researcher—let’s call him Igor—have found out about Witkoff using open-source intelligence, ie, stuff that’s been in the newspapers?

Well, Igor would surely have unearthed a lengthy 1998 Wall Street Journal profile, which recounts how, only three years previously, Witkoff was a small-time landlord in the Bronx who wore a licensed handgun on his ankle while out collecting rents uptown.

The piece did not paint a flattering picture of Witkoff’s burgeoning property portfolio, with a number of sources voicing concern about how highly leveraged his operation was.

The article upset Witkoff, who told a podcaster 20 years later: “I don’t have a thick skin.”

According to this piece, financiers were nervous about lending Witkoff more money. But he was lucky enough to meet a man named Mark Walsh, a managing director at Lehman Brothers, whom he described in terms nearly as flattering as those he later reserved for Putin: “One of the finest people I have ever met in my life.”

Walsh was more trusting of Witkoff than others and backed him to buy the landmark Woolworth building in Lower Manhattan in 1998. Lehman even had plans for Witkoff to launch a $2 billion IPO.

Well, we know how the Lehman story ended. In 2008, the bank came crashing down, with some people suggesting that Walsh bore a share of the blame. Igor will no doubt have discovered a 2009 New York Times piece asking of Walsh: “How could a real estate wizard... end up doing deals that contradicted everything he seemed to stand for and contribute to the collapse of one of Wall Street’s most venerable firms?”

Witkoff was more understanding and went back into business with Walsh in 2011. He told the WSJ, “Unfortunately, Mark has to live with the talk of having done a couple of bad deals rather than people focusing on the overwhelming amount of good ones.”

So, Igor will have built a picture of Witkoff’s striking appetite for risk.

And sooner or later, he will doubtless stumble upon another of his associates, Jho Low, often described as a “Malaysian playboy.” Like Walsh, Low was only too willing to lend Witkoff money, providing 85 per cent of the equity for a $654m deal to buy the Park Lane Hotel in 2013.

That arrangement also ended in tears, with the US Department of Justice claiming that Low had used fraudulent proceeds to buy his 55 per cent stake. The NYT reported that “he sits at the centre of what authorities are calling one of the biggest international money laundering schemes ever.” Low is currently reported to be hiding in Myanmar or holed up in Macau.

In his 2018 podcast, Witkoff claimed to have “vetted [Low] like we would vet any other partner.”

He was not to know that his business partner would one day be described as one of the most wanted white-collar criminals on earth.

Bad judgement or bad luck? You decide.

But here we are with Witkoff plucked from relative obscurity—at least in international diplomacy—to be the key figure tasked with negotiating peace in the two most intractable wars on the planet.

Igor will have filed all this—and more—back to the Kremlin. But he will also have watched Witkoff’s recent interview with Tucker Carlson in which he was exceptionally complimentary about Putin.

A key passage featured Trump’s envoy fumbling to name the Ukrainian areas seized by Putin:

“STEVE WITKOFF: I think the largest issue in that conflict are these so-called four regions. Donbas, Crimea. You know the names.

TUCKER CARLSON: Lugansk [sic]

STEVE WITKOFF: Yeah, Lugansk. And there’s two others. They’re Russian-speaking. There have been referendums where the overwhelming majority of the people have indicated that they want to be under Russian rule.”

In fact, the US State Department currently lists no fewer than six regions wholly or partly occupied by Russia: Donetsk, Kharkiv, Kherson, Luhansk, Mykolayiv, and Zaporizhzhya Oblasts.

The same official State Department report has no time for the so-called referendums approvingly referenced by Witkoff. “They are almost universally described as illegitimate… The US Government… does not and will not recognise Russia’s purported annexation of these territories.”

Witkoff, in other words, preferred spouting Kremlin propaganda to the long-standing policy of his own country.

Bad judgement or staggering naivety? You decide.

In the circumstances, it is unsurprising that the NYT reported earlier this month: “Some experts and diplomats who know Mr. Putin fear that Mr. Witkoff may be in over his head.” And that’s before we get onto Netanyahu or the Iranian president.

The infamous Signal chat group—involving Witkoff along with all the defence, intelligence and State Department bigwigs—gave the appearance of a bunch of amateurs running the show, not least because they were careless enough to invite a prominent journalist to eavesdrop on their plans to bomb the Houthis.

We must all hope that Donald’s golfing partner can pull off an extraordinary double feat of simultaneously bringing peace to Ukraine and the Middle East. Are you holding your breath? I doubt Igor is.