To Preserve Credibility And Leverage Trump Must Replace His Envoy Steve Witkoff In Future Negotiations With The Kremlin.
With Unacceptable Visible Admiration For Putin, Steve Witkoff Has Utterly Disqualified Himself.
We have previously discussed that the only member of the Trump administration who explicitly articulated the concrete costs that the administration would be prepared to impose in response to Russian intransigence was the retired General Keith Kellogg.
Notably, for taking this clear stance, Kellogg was sidelined and excluded from key meetings—most notably in Saudi Arabia, as well as in other direct engagements, including those with the Kremlin.
Recently, in the aftermath of the U.S.-Ukrainian agreement for a 30-day ceasefire—which Russia rejected, offering instead a limited “energy ceasefire”—it was Trump’s special envoy (to the Middle East), Steve Witkoff, who was tasked with delivering messages to Moscow and negotiating with the Russian side.
Now, even before last week’s comments made by Witkoff, his appointment to this role was already problematic due to his lack of crucial qualifications and expertise in dealing with the Kremlin.
Steve Witkoff is a real estate developer with no background in foreign affairs, diplomacy, or national security.
His appointment appears to be based not on merit, experience, or expertise, but solely on his status as a loyal Trump supporter.
He functions as an informal Trump spokesperson rather than a serious diplomatic envoy.
While Witkoff has not (until recently), said anything overtly absurd in public discourse, two comments he made last week raise significant alarm.
These comments demonstrate either a profound naivety or a dangerous level of admiration and trust for Vladimir Putin.
Let’s review these comments in turn:
1) “I tend to believe that President Putin is operating in good faith. He said that he was going to be operating in good faith to the President yesterday and I take him at his word. [emphasis added]”
and;
2) [Interview with Tucker Carlson] “You know, it got personal. The President, President Putin, had commissioned a beautiful portrait of the President Trump from the leading Russian artist. And actually gave it to me and asked me to take it home to President Trump, which I brought home and delivered to him. It's been reported in the paper, but it was such a gracious moment and [Putin] told me a story, Tucker, about how when the President was shot, he went to his local church and met with his priest and prayed for the President. Not because he was the President of the United, he could be become the President of the United States, but because he had a friendship with him and he was praying for his friend. It was, I mean, can you imagine sitting there and listening to these kinds of conversations? And I came home and delivered that message to our President and delivered the painting. And he was, he was clearly touched by it. So, this is the kind of connection that we've been able to reestablish, through, by the way, a simple word called communication…… [later comments] “I don’t regard Putin as a bad guy, that is a complicated situation” [emphasis added]”
Importantly, these are not mere rumors, such as the previously discredited story about Tulsi Gabbard referring to Trump and Putin as “friends”—a claim the Associated Press later withdrew (and where we published a correction and an apology).
In contrast, Witkoff’s statements are publicly available and verifiable through video recordings of his own speech.
Witkoff’s Apparent Trust & Admiration for Putin.
In these comments, Witkoff comes across as deeply enamored with Putin.
Either he is genuinely affected by Putin’s rhetoric, or he is exceptionally good at pretending to be.
(side note: if the latter, he deserves an Oscar for his performance.)
Regardless, the consequence is clear: Witkoff has disqualified himself as a credible envoy or negotiator with Moscow.
This disqualification stems from the perception—whether by Putin or others—that Witkoff is emotionally or ideologically compromised.
Witkoff simply cannot continue as a credible envoy and negotiator without causing much harm to the credibility and leverage of the U.S.
There are a number of significant issues that would remain if Witkoff was allowed to continue business as usual:
1) Absence of a credible potential hardliner dealing directly with Putin.
A good envoy and a negotiator must be credible if he needs to dial up his ‘‘bad cop’’ face.
If Putin (wrongly or rightly) believes that Witkoff admires him or views him as negotiating in good faith, then there is no space for Witkoff to deliver hard messages or act as a credible threat.
Witkoff simply cannot play the role of the “bad cop” in any negotiation dynamic.
Now, one might argue that diplomacy often works best with a good cop–bad cop pairing, and that Witkoff’s softness could be balanced by someone more confrontational.
But the problem is that the only figure who plausibly played that role—Keith Kellogg—has already been sidelined.
No one else in the administration appears willing or capable of directly challenging Russian narratives or issuing credible threats.
Even Secretary of State Marco Rubio, who might otherwise serve in this role, does not appear to be taking a central direct position in the negotiation process.
As a result, we are left with a Trump loyalist who seems enamored with Putin, shuttling back and forth between Washington and Moscow in a dangerous form of “personal diplomacy” - a dynamic that Putin would be utterly foolish and reckless not to exploit.
2) Even higher Risk of Disinformation and Misjudgment.
If Witkoff genuinely believes that Putin is acting in good faith, he will undoubtedly influence Trump with that perception.
This will increase the likelihood that Trump continues to buy into Kremlin misinformation—such as the claim that Ukraine is the party violating the ceasefire.
3) Incentivizing Putin To Stall And Make Additional Gambles.
Even if Witkoff does not truly believe this ‘‘good faith’’ narrative but Putin believes that he does, it creates a new strategic risk: Putin could miscalculate, assuming that Witkoff will whitewash any violation, thereby encouraging more belligerent Russian behavior.
This misperception of leverage could stall negotiations or derail them altogether.
4) Damage to Allied Trust and Credibility.
Another dangerous risk stems from the reaction of U.S. allies, especially Ukraine and European partners.
Many are already skeptical of Trump’s foreign policy reliability.
And the additional perception that one of the chief U.S. negotiators with the Kremlin is a Putin sympathizer—who believes in some sort of Trump-Putin camaraderie and views Putin as a good-faith actor—could severely erode trust even further.
This perception would lead Ukrainians and Europeans to question the value of continued U.S. involvement in negotiations: why should they trust a process led by someone who seems sympathetic to the Kremlin?
The result could be a race by allies toward Plan B—ramping up preparations for further escalation, and abandoning hopes of a meaningful ceasefire.
This would mark a dangerous breakdown in alliance coordination, as European and Ukrainian actors begin to view U.S. diplomacy not just as ineffective, but actively harmful.
The conclusion of our European allies will be that the Kremlin now has a direct channel to Trump, via Witkoff, bypassing traditional foreign policy mechanisms.
The end result is a deterioration of Trans-Atlantic and Washington - Kyiv trust, an emboldened Kremlin, and an unraveling of any credible diplomatic leverage the United States hoped to maintain.