Diplomacy for Sale: How Witkoff and Co. Cut a Deal with Russia

A Moscow-friendly deal that sells out Ukraine exposes how Witkoff and others are reshaping diplomacy for profit.

Nov 26, 2025

In a bombshell that should really surprise nobody, Bloomberg just reported that Steve Witkoff, the US Special Envoy to the Middle East, Russia, and apparently wherever else there’s money to be made, has actually been advising Kremlin apparatchiks on how to most effectively manage the President.

“Zelensky is coming to the White House on Friday,” Witkoff told Ushakov, “I will go to that meeting because they want me there, but I think if possible, we have the call with your boss [Putin] before that Friday meeting.”

In short, Witkoff appears to have been cooperating with the Russians to figure out how to most effectively advocate for their interests in the White House. This offers additional insight how Trump’s 28-point Russia-friendly plan to “end the war in Ukraine” came to be. But as dangerous as this plan is, it’s not just the content of the deal—which would force Ukraine to cede territory and constrain its military, undermining the very meaning of sovereignty—that is alarming. It’s also the process behind it.

How the administration arrived at this plan signals either gross incompetence or a fundamental shift in diplomatic priorities, one that has very little—if anything—to do with America’s geopolitical interests. Now, normally I would adhere to Hanlon’s Razor: “Never ascribe to malice that which could be adequately explained by incompetence.” Given Trump’s willingness to speak ill of just about every world leader other than Putin, however, my money is on something other than incompetence this time around.

We’ve seen much of the back-and-forth around whether or not this was an American proposal or a Russian one. First, we heard that this was Trump’s proposal to Kyiv. Recognizing the growing concern from both parties at the overtly pro-Russian nature of the plan, Rubio quickly sought to reassure Senators that the proposed plan was just a Russian proposal which the US was “passing along” to Ukraine. This was in turn quickly denied by the White House, leaving Rubio to publicly walk back what we can only assume he said to Senators privately. Meanwhile, the Trump Administration’s Ukraine Envoy, General Keith Kellogg, a three-star General with a lifetime of experience in international affairs, has been notably absent from any of the relevant conversations that should, presumably, have been at the very top of his portfolio.

In short, the National Security Advisor/Secretary of State, the person who is supposed to be in charge of coordinating America’s foreign policy across a sprawling federal government appeared to know nothing about the nature or origin of this deal. Neither did the Envoy charged with matters related to Ukraine. The absolute best case scenario is that this represents an incredible demonstration of ignorance and incompetence at the highest levels of government.

The much more realistic scenario, particularly in light of Bloomberg’s recent reporting, is that Witkoff, whose primary qualification appears to be his wealth and personal loyalty to the Trump family, was able to privately negotiate the terms of this deal with Russia’s Special Envoy, Kirill Dmitriev, excluding anyone in the administration who could ensure that appropriate diplomatic procedures were followed and US national security interests were properly considered. As a quick reminder, Witkoff is the same guy who, just a few short months ago, went to Moscow to speak with Putin and rather than bringing his own translator, chose to use one provided to him by the Kremlin, who, quite possibly, turned out to be a Russian agent. Because… Of course…

Ultimately, I believe that the focus on whether this was a mismanaged rollout of a Russian proposal or an even more mismanaged presentation of an American one is irrelevant because the answer won’t change anything. If the plan was Russian, why were we trying to pass it off as our own and why were we pressuring the Ukrainians to accept it? And if it was American, then why on earth would we essentially take Russia’s side and pressure Ukraine to capitulate? As with any crime, we should be asking: “who stood to gain?”

All of this becomes a lot easier to understand if we stop thinking of Trump, Witkoff, Putin, and Dmitriev as political leaders of opposing powers and instead think of them as leaders of competing but friendly mafia families dividing up territory and clout. Looking at the deal they concluded and the rhetoric emanating from both camps, it’s not too hard to get into that mindset. Nothing about this deal would ensure peace over the long (or even medium) term. Instead, this is merely a breather, offering Russia the chance to consolidate its gains and bide its time until it can attack again while the US, and more importantly, those in Trump’s immediate circles, have a chance to profit from doing business with Russia.

It does not take any great leaps of logic to come to this conclusion. From the Russian Foreign Minister stating that any deal would have to reflect the letter and spirit of Putin and Trump’s understanding from the Alaska Summit (I wonder what was agreed at the Alaska Summit…) to the recent revelations about just how cozy Witkoff has become with Russia’s leadership, I promise that you don’t have to be a chess master to understand the board.

Last week, I talked about how President Trump was privatizing American power at home. Today, this 28-point plan outlining Ukraine’s capitulation and the abandonment of American national security interests in Europe is what the privatization of American power looks like on a global scale.