Politics

Trump’s ‘Rogue’ Envoy Blamed for His Endless Humiliations by Putin

PUTIN'S SECRET WEAPON

Steve Witkoff’s unprofessionalism is having significant consequences on the world stage.

U.S. President Donald Trump (R) and Russian President Vladimir Putin arrive for a press conference at Joint Base Elmendorf-Richardson on August 15, 2025 in Anchorage, Alaska.
Andrew Harnik/Getty

Donald Trump’s special envoy to the Middle East, Steve Witkoff, is being blamed for the failure of the president’s summit with Vladimir Putin in Alaska, with colleagues becoming increasingly frustrated with his unprofessionalism.

“He’s kind of a rogue actor,” a senior White House staffer told Politico. “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.”

Sources told the news outlet that Witkoff refused to consult experts or prepare for meetings in the lead-up to the historic summit in Alaska, where Trump failed to secure a peace agreement in Ukraine. The envoy assumed, like Trump, that his personal charisma and rapport with the Russian president would be enough to force a breakthrough.

“The thing is, Witkoff isn’t consistently engaged,” a White House source told Politico. “He will pop in for a visit to Vladimir Putin, say a bunch of stuff, not tell anyone what really happened, and then just f--- off to his life again.”

WASHINGTON, DC - MAY 28: U.S. Special Envoy to the Middle East Steve Witkoff delivers remarks during the swearing in ceremony for interim U.S. Attorney for Washington, D.C. Jeanine Pirro in the Oval Office of the White House on May 28, 2025 in Washington, DC. Trump has announced Pirro, a former Fox News personality, judge, prosecutor, and politician, after losing support in the Senate for his first choice, Ed Martin, over his views on the January 6, 2021 attack on the U.S. Capitol. (Photo by Andrew Harnik/Getty Images)
Steve Witkoff is a former real estate developer with no prior experience in diplomacy. Andrew Harnik/Getty Images

“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,” they added.

Witkoff has met with Putin five times over the past six months, but little is known of what was said between the two men behind closed doors. A former real estate developer with no prior experience in diplomacy, Witkoff views the negotiations through the lens of real estate, thinking of the conflict as merely a land dispute, Politico reported.

According to Politico, Witkoff’s failure to read intelligence briefings, check his government emails, or take notes at meetings has led him to parrot Putin’s talking points about the state of the frontlines in Ukraine and misinterpret his position, which, by proxy, may have influenced Trump’s understanding of the situation.

“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 source told the publication.

Following his last meeting with Putin before the summit in Alaska earlier this month, Witkoff returned to the White House with news of a major breakthrough—Putin had agreed to a land-swapping deal in eastern Ukraine in which Russian forces would withdraw from the occupied regions of Zaporizhzhia and Kherson in return for Kyiv ceding Donetsk and Luhansk. With this information, Trump would negotiate the details in Anchorage.

TOPSHOT - In this pool photograph distributed by the Russian state agency Sputnik, Russia's President Vladimir Putin greets US Special Envoy Steve Witkoff prior to their talks in Moscow on August 6, 2025. (Photo by Gavriil Grigorov / POOL / AFP) (Photo by GAVRIIL GRIGOROV/POOL/AFP via Getty Images)
Witkoff has refused to take notes or share details of his meetings with Putin. Gavriil Grigorov/Pool/AFP via Getty Images

The news shocked world leaders, who were adamant that Putin would never give up occupied territory in Ukraine.

The next day, further talks between White House and Kremlin officials revealed that Putin had said nothing about withdrawing from the occupied territories and merely conceded that he would not demand that the West formally recognize them as Russian, according to Reuters. Witkoff had misinterpreted Putin’s demand that Ukraine withdraw from Zaporizhzhia and Kherson as a concession offer.

President Donald Trump and Russian President Vladimir Putin shake hands at the end of a press conference at Joint Base Elmendorf-Richardson on August 15, 2025 in Anchorage, Alaska where they did not take any questions and did not reveal anything had been achieved at their meeting besides a promise for more talks.
President Donald Trump and Russian President Vladimir Putin failed to reach a peace agreement at the bilateral summit in Alaska earlier this month. Andrew Harnik/Andrew Harnik/Getty Images

Witkoff disputed Politico’s characterization of him, telling the outlet: “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.”

Vice President JD Vance has also praised his colleague’s work ethic, saying, “Witkoff has made more progress towards ending the bloodshed in Ukraine than all his critics combined.”

Witkoff was set to meet with top Ukrainian officials on Friday to discuss technical details he hopes will lead to a three-way summit between Trump, Putin, and Ukrainian President Volodymyr Zelensky. Kyiv remains cautiously optimistic.

“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,” a Ukrainian official said, adding they hope Witkoff will be receptive to their positions.

White House Deputy press secretary Anna Kelly told the Daily Beast: “It’s typical for the TDS-ridden activists and fake ‘journalists’ of the Daily Beast to regurgitate fake news just to undermine President Trump and his team.

“Like President Trump, Steve Witkoff left behind a massive business enterprise to serve his country, and he is doing an incredible job advancing peace around the world. Over 70 Americans detained abroad have returned home as a direct result of Mr. Witkoff’s efforts, and the President has full confidence in Mr. Witkoff’s ability to advocate for America First foreign policy.”

The Daily Beast has contacted the State Department for further comment.

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