With Allies Like These Steve Witkoff Does Not Need Enemies
Anatomy of a devastating Politico story.
A running theme of my public writings — one that has spanned both terms — is that Donald Trump’s administrations are rife with exercises in beclowning the executive branch. As time has passed and Trump has fired or alienated the semi-competent people who agreed to work for him, he has selected folks who excel in sycophancy and little else.
The result in 2025 has been a foreign policy omnishambles. Trump’s cabinet might fawn all over him, and to be fair there are a few de facto cease fires that have been codified in the White House. Mostly, however, the foreign economic policy has been an exercise in horrible economic experimentation — and the security side of the equation has been even worse. Trump’s two military campaigns in the Middle East did not accomplish much of anything. There is no cease-fire in Gaza and the country is turning against Israel because of its genocidal actions in the occupied territories. I still don’t see a coherent China strategy emerging from the Elbridge Colbys of this administration.
Oh, and Russia and Ukraine are continuing their war despite Trump’s pledge to end it within 24 hours of his inauguration.
None of this looks great. Unsurprisingly, there has been a desperate White House effort to apply gold plating on all the piles of shit that Trump’s foreign policy has yielded.
Which brings us to their defense of Steve Witkoff, Donald Trump’s peace envoy for Russia, Iran, and Gaza.
Politico’s Felicia Schwartz has a doozy of a profile on Witkoff. The title is indicative: “‘His inexperience shines through’: Steve Witkoff struggles to manage Russia as Trump peace envoy.”
The lede is pretty bad too:
President Donald Trump’s surprise Anchorage summit with Russian President Vladimir Putin could have been a signature achievement for Steve Witkoff, the developer-turned-diplomat who facilitated the meet up.
But promised follow-up meetings between Putin and Ukrainian President Volodymyr Zelenskyy have not materialized, ceasefire demands were dropped, threats of tough action have disappeared and Trump’s team has offered no clear road ahead.
Some frustrated U.S., Ukrainian and European officials say part of the problem is the go-it-alone style of Witkoff, Trump’s special envoy for peace missions and go-to negotiator on Ukraine. He has refused to consult with experts and allies, leaving him uninformed at times and unprepared at others, according to seven people familiar with internal discussions. Two said he misses the mark by viewing the conflict through a real estate lens, like a land dispute.
Trump’s unconventional fixer has met Putin five times over six months, but he has yet to translate his access to the Russian leader into any breakthroughs on Ukraine.
You should read the whole thing, as it’s pretty damning. It is chock full of embarrassing quotes from U.S. officials like, “His inexperience shines through, he has the president’s ear, which is evident, but there has been some confusion about what has been said and agreed” and “He’s kind of a rogue actor. He talks to all these people, but no one knows what he says in any of these meetings. He will say things publicly but then he changes his mind. It’s hard to operationalize that.”
The other details in the story are also, how you say, not great. Schwartz writes that “His staff, to the extent he has any, often doesn’t know where he is or what he is doing, according to four people familiar with the dynamics of the office.” Also, “Witkoff at times appears to struggle to focus on more than one task at a time…. He is not a voracious consumer of his intelligence briefing materials and doesn’t read them every day…. Witkoff rarely reads his government email.”
So this all seems horrible. But the hard-working staff here at Drezner’s World has read enough hit pieces to know that sometimes the juiciest details come from those in the U.S. government who are nursing a grudge. For example, the fact that Schwartz discusses Witkoff’s failure to consult with experts and allies suggests that maybe it is said experts and allies who spilled the most tea to the Politico reporter.
Instead, let us turn our attention to the attempts by Wtkoff’s supporters to defend him. The Trump White House has tried to push back on Schwartz’s story. And it’s here that one realizes even Witkoff’s backers are damning him with faint praise.
Here are a list of the supportive statements in the Politico piece… followed by my deconstruction of them in italics:
“A second senior administration official defended Witkoff’s approach, saying the outcomes of his diplomacy ‘speak for themselves, in the form of the historic bilateral meeting [between Trump and Putin] and European leaders coming to the White House less than 48 hours later.’” Um… meetings themselves are not important outcomes! And it’s no surprise that the meetings happened! Putin was delighted to secure a bilateral meeting on U.S. soil. Ukraine and its European allies were eager to push back on Putin’s rhetoric in the Oval Office. The lack of forward progress since these meetings is evidence enough that nothing of substance was achieved.
“The second senior administration official said that Witkoff has plenty of access to expertise, adding that he is in regular communication with Secretary of State and acting national security adviser Marco Rubio, along with National Security Council officials ahead of conversations with Putin and other leaders.” To put it gently, Rubio is not a Russia expert, and Trump has denuded his NSC staff of significant expertise. This is not the brag the senior administration official thinks it is.
As a sign of Witkoff’s success, the official pointed to comments from Finnish President Alexander Stubb, who said during the White House meeting 11 days ago, ‘in the past two weeks we’ve probably had more progress in ending this war than we have in the past three and a half years.’” Pro tip: any time a small allied state is showering praise on Trump it is because they are placating a petulant, immature leader who only wants to hear praise.
“After hearing about POLITICO’s reporting, the White House sent over laudatory statements from six people. In one of those, U.K. National Security Adviser Jonathan Powell said Witkoff ‘has been able to open doors that no one else could’ and ‘is exactly [the] sort of person’ who gets results in diplomacy by concentrating ‘on building trust between key leaders … and moving quietly to cut a deal.’” Honestly, this is confusing. Trump’s comments over time suggests he trusts Putin less than he did at the start of his second term. Meeting with Trump did not require opening a door that no one else could — it’s just that no one wanted to open it. So I don’t see anything groundbreaking here.
“Vice President JD Vance said ‘Witkoff has made more progress towards ending the bloodshed in Ukraine than all his critics combined.’” You know what? Vance is correct, but the reverse is true as well. That is because no progress has been made by anyone. The best thing one can say about Witkoff is that he has tried but has had zero success.
“The second senior administration official [said] Witkoff checks his government email daily and receives a daily intelligence briefing.” If you are in government and only checking your email once a day you are a useless lump of flesh who has little idea of how to coordinate policy.
Even the Trump administration’s attempts to boost Witkoff’s bona fides fall flat. And if you think about it, that is the most damning indictment of Witkoff that there is.
It's true that he has opened doors, but at the Kremlin, to be bamboozled by Putin. It would have been best for him not to open them in the first place. 😅
Witkoff''s proud ignorance, his belief that he can just wing it, is a perfect fit for this shambolic regime.