Trump's unlikely backchannel raises a major question: can unconventional diplomacy break the stalemate in Ukraine?

In a recent interview, Donald Trump did something surprising that almost no one noted at the time: He placed a relatively obscure real-estate developer, Steve Witkoff, at the center of some of the most delicate geopolitical negotiations on earth. And not just Middle East diplomacy, either, where Trump and his team — Jared Kushner, Avi Berkowitz, and others — famously brokered the Abraham Accords, but the Russia-Ukraine war itself.

Who is Steve Witkoff, and why does Trump believe he could help end the largest European conflict since WWII?

Last month, Witkoff met with Vladmir Putin as Trump’s envoy.

Trump’s telling of their meeting is pure Trump: kinetic, punchy, and laced with the kind of personal loyalty he values as much as conventional résumés. He introduced Witkoff as “a great businessman” and “a great negotiator,” but added that those qualities alone don’t make him special. 

What matters to Trump — far more — is that Witkoff is “a great guy,” someone universally liked and trusted. In Trump’s world, likability isn’t a soft skill; it’s leverage. “Everybody loves him,” Trump said. “Everybody… on both sides.”

And that’s where Trump’s argument really begins.

Witkoff’s Five-Hour Meeting With Putin

President Trump arranged for Witkoff to meet Vladimir Putin in Moscow. Witkoff, a man with “no idea about Russia” and little political background, went in for what Trump assumed would be a brief, polite 15-minute handshake.

It lasted five hours.

Trump repeatedly called to check on Witkoff’s progress. At 30 minutes, at an hour, at two hours — Witkoff was still in the room with Putin. “Most people I’d send in, number one, they wouldn’t be accepted,” Trump joked during the interview. “Number two, if they were, the meeting would last five minutes.”

Five hours with Putin is not something the average American businessman accomplishes. For Trump, that is proof of Witkoff’s unique value: he can connect. He can disarm. He can sit across from hardened political operators and simply be himself — and somehow that works. Trump, never shy of grand comparisons, even called him “Henry Kissinger, who doesn’t leak.”

This is where the speculation becomes interesting. Trump clearly intends to use informal envoys — trusted confidants, friends, businesspeople — to explore cease-fire frameworks behind the scenes. That’s not new; American presidents have done it for decades. What is new is the idea of someone like Witkoff, not a seasoned diplomat, becoming an intermediary between Trump and Putin during an active war.

Could It Actually Work?

On one level, the idea sounds improbable. The Russia-Ukraine is a brutal, grinding, multi-front conflict with catastrophic human toll, competing historical claims, and security guarantees that will shape Europe for generations.

But Trump’s point isn’t that Witkoff is a geopolitical theorist. It’s that he has a human superpower — what old-school diplomats used to call “the gift of the room.” He can get people talking. He can build rapport. And for Trump, whose entire foreign-policy philosophy can be summarized as “you make peace with the people who can stand you, not with the people who can’t,” that quality is priceless.

The United States will never negotiate an end to the war on Ukraine’s behalf. Kyiv will always lead that process. But a Trump-backchannel aimed at testing Putin’s red lines and probing whether there is any conceivable formula for a cease-fire: territorial freezes, demilitarized zones, security guarantees, phased sanctions relief, or some hybrid of the above.

Trump genuinely believes the war “would’ve never happened” if he were president, and he now portrays ending it as a central mission of his second term.

The Middle East Comparison

Trump also pointed to the Israel-Gaza ceasefire and broader Middle East realignments — achievements he described as “the most challenging breakthrough maybe ever” — as proof that unconventional diplomacy works. He framed it as a sweeping strategic shift: demilitarization of Gaza, disarmament of Hamas, and regional unity that would’ve been unthinkable a decade ago.

He credited Witkoff and Jared Kushner as examples of people who could “get the job done,” not because they read the right white papers, but because they approach negotiation the way Trump does: personally, directly, relentlessly.

If that formula produced the Abraham Accords — and it did — Trump sees no reason it cannot be tried in Eastern Europe.

And that brings us back to Steve Witkoff.

Is he going to single-handedly end the Russia-Ukraine war? No. But could he serve as a trusted backchannel for a president who values loyalty, secrecy, personal chemistry, and unorthodox approaches to diplomacy? Absolutely.

Witkoff represents Trump’s belief that diplomacy is, at its core, a human enterprise. It’s about who can stay in the room the longest — and who can get the other side to stay there with them.

Five hours with Putin may not solve a war.

But in a world where almost no one can talk to anyone anymore, five hours might be a start.

(Contributing writer, Brooke Bell)