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.

There were many barriers to the summit in Anchorage yielding results — Putin’s unwillingness to make significant concessions to end his war against Ukraine the major one, but many of those familiar with Witkoff’s role in the negotiations with Russia say he has made talks more difficult.

Witkoff is still trying to make inroads.

He is meeting Friday in New York with Andriy Yermak, head of Zelenskyy’s presidential office, part of an effort to get Russia and Ukraine meeting for technical talks ahead of an eventual trilateral summit. The lower level discussions between Russian and Ukrainian officials, should they happen, are expected to cover territory, security guarantees and other issues and to pave the way for higher level conversations, a senior administration official said.

“What we’re trying to do is put Putin and Zelensky together and create the opportunity to have a successful meeting,” Witkoff said in an interview.

This article is based on conversations with 13 people, including U.S. and foreign officials and other people familiar with the diplomatic effort to end Russia’s war on Ukraine. Many were granted anonymity to discuss sensitive negotiations and internal deliberations.

A number of those people argue that the war is much more complex than Trump’s confidant seems to grasp, and blame him for American efforts that have yet to net any meaningful concessions from Moscow.

“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,” said a person familiar with the diplomatic effort.

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.”

That’s not enough to declare success, his detractors say.

“He’s kind of a rogue actor,” said a U.S. official familiar with Witkoff’s diplomatic style. “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.”

Witkoff’s Washington office is sparsely staffed, and short on people with Russia expertise or experienced in complex diplomatic negotiations. And he has refused to do typical consultations with Russia and Ukraine experts in and outside of government, according to the five people familiar with internal discussions.

Different definitions of success

The summit in Alaska was notable in part because of how little preparation went into it. Typically ahead of such a high-profile meeting, foreign ministers and lower level staffers reach agreement on the choreography and outcomes ahead of time to make sure the meeting is productive and worthwhile.

The new goal of organizing lower-level technical meetings suggests Witkoff’s team may be returning to a more traditional approach and is a reversal from the White House’s previous insistence on the importance of bringing the leaders together immediately.

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.

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.”

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.”

In another, Vice President JD Vance said “Witkoff has made more progress towards ending the bloodshed in Ukraine than all his critics combined.”

Free-wheeling style

People familiar with Witkoff’s style liken it to Trump’s free-wheeling approach of doing business.

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. They said he spends most of his time at his office in the White House, while the rest of his team is at the State Department.

“The thing is, Witkoff isn’t consistently engaged. He will pop in for a visit to Vladimir Putin, say a bunch of stuff, not tell anyone what really happened and then just fuck off to his life again. Meanwhile, the Russians are talking to you about how ‘Witkoff says…’ and you don’t know whether they’re right or not, but you can’t get a readout from the Russians,” the U.S. official said.

Witkoff at times appears to struggle to focus on more than one task at a time, the U.S. official and another one of the people said, adding that when a flurry of developments occurs in one portfolio, say Gaza or Iran or Ukraine, other priorities take a backseat. He is not a voracious consumer of his intelligence briefing materials and doesn’t read them every day, the second person said.

Witkoff rarely reads his government email, according to one of the people and the U.S. official familiar with his role.

The second senior administration official rejected this characterization, saying Witkoff checks his government email daily and receives a daily intelligence briefing. After receiving criticism for using Putin’s translator in Russia, Witkoff now uses a State Department translator during official meetings, the official said.

New positions, new challenges

Part of the issue for Witkoff may be the manner in which he came into his role as chief Ukraine negotiator. During the transition after the 2024 election, Trump named Witkoff to be his special envoy for the Middle East, while Trump named Keith Kellogg as the special envoy for Russia and Ukraine.

At that time, many State Department Russia and Ukraine experts went to work for Kellogg, a second U.S. official said.

But Kellogg was sidelined in dealing with Russia after Moscow complained about him, as POLITICO previously reported. Witkoff became the de facto Putin go-between after he made his first trip to Russia in February to secure the release of a detained American schoolteacher and kick off a monthslong effort at rapprochement after he made the prisoner deal with Moscow.

But many of the staff that specialize in the region stayed at Kellogg’s office, leaving Witkoff’s office with no dedicated Russia or Ukraine experts, the second U.S. official said. That hasn’t changed even as his official remit has expanded to “special envoy for peace missions” to include a number of global disputes.

Discontent on Russia’s side

Witkoff’s Russian interlocutors are also frustrated, particularly with his inability to properly convey Putin’s messages and red lines to Trump, according to the person familiar with his diplomatic efforts, another person familiar with the matter and the first U.S. official.

Russian officials value that Trump has sent someone who is close to the president and can speak for him, but are concerned that Witkoff doesn’t fully understand what Putin is telling him, they said.

Witkoff made a trip to Moscow this month to try to make headway with Putin before Trump’s now-lapsed deadline on steep tariffs for purchasers of Russian oil.

Witkoff left his August visit with Moscow convinced that Russia had agreed to significant territorial concessions — shaping his advice to Trump that the president should grant Putin the one-on-one summit he had long sought, the second U.S. official said.

When he returned to the U.S., Witkoff and Trump both touted those concessions on territory in Eastern Ukraine. His European and Ukrainian interlocutors did not see it that way, the second U.S. official and one of the people familiar with the diplomacy said.

Witkoff said he has not misconstrued the message coming from Moscow.

“I have tremendous support from the State Department, from lots of Russian experts. There’s a lot of very smart people in our system. And not one of them, not in our system, not one of them on the U.S. side has ever said to me, ‘you missed something here,’” he said.

In the discussions, Russia has offered what the Trump administration sees as a significant compromise, a senior administration official said. Under the deal, the U.S. would recognize Russian control over Luhansk, Crimea and Donetsk at their official boundaries and Kherson and Zaporizhia at the contact line, or battle lines on the ground.

“Never before had there been any discussion about this, a compromise on the regions,” the senior administration official said.

But many of Washington’s European and Ukrainian partners do not see this as Russia meaningfully yielding, the second U.S. official said. Such a deal would require Ukraine to withdraw from some of its most heavily fortified territory in Donetsk. Ukraine and its allies see that as legitimizing Putin’s land grab.

Putin’s talking points coming through

There are other instances that have frustrated U.S. and European officials well. In a CNN interview after Trump and Putin’s Alaska summit, Witkoff said Moscow had conceded that Ukraine’s Western partners could provide security guarantees modeled on NATO’s Article 5, which obligates members to treat an attack on one as an attack on all.

However, two of the people familiar with the matter said, Russia had actually suggested conditions similar to those it offered in 2022 during ultimately failed peace talks in Istanbul — that Ukraine could have a so-called deterrence force but that Russia would have a veto over when it was used.

As one person familiar with Witkoff’s role in the process put it: “There’s what Russia says, and what Russia means.”

The second senior administration official said Witkoff “understands all the complexities.”

When Witkoff flies to Moscow, he uses his own plane and brings no policy experts. He is usually only accompanied by his chief of staff, a translator and diplomatic security, according to two people familiar with the matter and the second senior administration official, who added that he pays for all of it himself.

Following the Alaska meeting, European officials have impressed upon Witkoff and Trump the strategic importance of the Donbas region for Ukraine — and how ceding all of it, including territory Russia hasn’t captured, is unacceptable to Kyiv, according to two of the people familiar with internal discussions.

“He seems to have bought into the false Russian narrative that they are winning on the front lines, which we all know is not true,” another one of the people familiar with the discussions said.

Witkoff rejected this characterization.

“What I’m here to do is actually bring two sides together, narrow the issues and get it to a place where we can build political capital and fix this stupid thing,” he said.

At the White House last week, the assembled European leaders likened giving up the Donbas to giving up Florida, trying to phrase it in ways that Trump and Witkoff could grasp, two of the people familiar with internal discussions said.

Some of Ukraine’s allies have suggested comparing the area to the Golan Heights in Israel, likening the strategic importance to another area of the world Witkoff is better steeped in, one of the people said.

Ukraine’s allies look for other avenues

European and Ukrainian officials are buoyed by the presence of other officials working on the process. Kellogg, damaged from his sidelining this year, has managed to come back more into the fold.

But allies were disappointed to see that Kellogg, whose approach they prefer to Witkoff’s, was left out of the Alaska trip after clearing his schedule to go.

Kellogg did later join the meetings with the Europeans in Washington, reassuring those who think he has a more clear-eyed view of the war than Witkoff does, according to the person familiar with internal discussions and another person.

Missteps with Russia aside, European and Ukrainian officials are thrilled that the intense diplomacy of the past several weeks has led to a serious conversation on security guarantees and what the U.S. and Europe would commit.

But, both U.S. officials noted, this process is being led by Rubio and Joint Chiefs Chair Gen. Dan Caine, both of whom they much prefer to work with and feel have a clearer-eyed take on the war.

Ukraine, meanwhile, is hoping that Witkoff’s Friday meeting brings new options. A Ukrainian official said the meeting comes after Yermak and secretary of the Ukrainian National Security Council Rustem Umerov visited Qatar to scout the country as a possible location for a meeting between Zelenskyy and Putin.

“Our main focus is to reiterate that Ukraine is ready to meet Russia at the presidential level but Russia continues to delay the process and constantly invents new pretexts as to why to delay it,” the Ukrainian official said, adding that they hoped Witkoff would be receptive to their arguments.

Nahal Toosi and Jack Detsch contributed to this report.