The Appalling Broken Record of Steve Witkoff Stories

The basic narrative is pretty clear at this point. But with each drip in this story, the larger picture comes into focus.

Photo by Kevin Andre on Unsplash

The hard-working staff here at Drezner’s World has written juuuuust a few newsletters about Steve Witkoff, Donald Trump’s extra-special envoy to the Middle East. A few of the greatest hits:

1. March 24th: “Yes, it’s safe to say Witkoff has underestimated the complications of the job.”

2. August 29th: “Even Witkoff’s backers are damning him with faint praise.”

3. November 25th: “For Trump, tolerating a freewheeling, bottom-up approach to intractable foreign policy conflicts offers the possibility of a way out…. [but] it makes it easy for well-connected foreign actors to pick and choose among the most pliable of Trump subordinates.”

4. November 30th: “Witkoff is spectacularly out of his depth — which means that he’s ginning up ideas with little understanding of the problem that he is trying to solve.”

All of these newsletters were written in response to either Witkoff freely demonstrating his ignorance or in-depth reporting in which multiple sources confirm Witkoff’s dubious foreign policy style. At this point it has become something of a broken record…. that is playing on a phonograph which is losing battery power. It’s both repetitive and awful.

The Witkoff narrative that emerges from these stories is clear. In short, Steve Witkoff:

• Possesses minimal knowledge of world history or world politics;

• Rejects consultation with officials who do know something about world history or world politics;

• Shares Trump’s belief that leader-to-leader business deals are the pathway to peace;

• Thinks material incentives are the way to secure peace from leaders who are far more interested in imperial expansion;

• Freelances to the point of not being entirely on the foreign policy reservation;

• Possesses such autonomy because Marco Rubio is the only person minding the foreign policy store and is doing a piss-poor job of it;

The Witkoff story that is prompting this particular newsletter is another Wall Street Journal bombshell with six bylined reporters: “How Putin Got His Preferred U.S. Envoy: Come Alone, No CIA.” The opening is a doozy, revealing that Putin wanted Witkoff as his interlocutor — and for good reason, Witkoff was a willing patsy:

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 blockading Russia’s troubled economy.

It is hard to pinpoint a moment in history when businessmen have held such direct sway over matters of war 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.

The rest of the 3,300+ word story confirms every element of the Witkoff narrative and extends it to Jared Kushner as well. The story notes that Kushner believed that the Abraham Accords “as a model for what he and Witkoff could arrange between Russia and Ukraine.” This is nuts on multiple levels — not the least of which is that the prospect of Saudi Arabia joining the Abraham Accords was a trigger for the horrific October 7th attacks and Israel’s devastating response. The story also details how both Witkoff and Trump have rejected any intelligence briefings on Russia.

The most ruefully amusing thing in the entire story is the observation that Witkoff himself is “aware of the criticism that he is bumbling his way through diplomacy of the highest stakes.”

About a week ago, Politico’s Felicia Schwartz and Eli Stokols wrote about the U.S. effort to provide security guarantees to Ukraine that are “Article V like” without actually being a Ukraine-within-NATO-honest-to-goodness Article V commitment. Beyond the problem of no one being aware that this was kinda sorta tried already, there are some breathtaking claims made by anonymous U.S. officials in that story:

“The basis of that agreement is basically to have really, really strong guarantees, Article 5-like,” a senior U.S. official said. “Those guarantees will not be on the table forever. Those guarantees are on the table right now if there’s a conclusion that’s reached in a good way.”….

The discussions over the weekend largely focused on detailing the security guarantees that the U.S. and Europe would provide Ukraine, but they also included territory and other matters. Witkoff and Kushner were joined by Gen. Alexus Grynkewich, head of U.S. European Command as well as the top commander for NATO.

The U.S. expects that Russia would accept such an arrangement in a final deal, as well as permit Ukraine to join the European Union. That could prove to be an overly optimistic assessment, given the Kremlin’s refusal to give ground in peace talks so far. And Moscow has yet to weigh in on any of the new agreements being worked out in Europe over the last few days.

“We believe the Russians, in a final deal, will accept all these things which allow for a strong and free Ukraine. Russia, in a final deal, has indicated they were open to Ukraine joining the EU,” a second U.S. official said. (emphasis added)

I have no idea which U.S. official said the bolded portion to Politico. But I’ll put fifty bucks on it being either Jared Kushner or Steve Witkoff. Both of them are clueless enough and self-confident enough to say something that delusional.