Growing Concern in Trump Administration Over Witkoffs Unsupervised Meetings with Putin

Insiders from the Trump administration are reportedly growing increasingly uneasy about special envoy Steve Witkoff’s private meetings with Russian President Vladimir Putin, as detailed by the New York Post on Wednesday, citing anonymous sources familiar with the situation.

Witkoff, an ex-real estate attorney and investor known for his tough negotiation skills, has allegedly met with Putin four times since February, without any seasoned diplomatic advisors or approved interpreters, which deviates from established U.S. diplomatic practices.

During their latest meeting last Friday at the Kremlin, Putin was accompanied by senior aide Yury Ushakov and Kirill Dmitriyev, head of the Russian Direct Investment Fund. A video from the Kremlin showed Witkoff questioning whether the individual sitting next to him at the table was “from the embassy.”

Originally designated as the Middle East special envoy when Trump assumed office in January, Witkoff has since broadened his responsibilities to include serving as an ambassador-at-large, focused on negotiating an end to the conflict in Ukraine.

His unmonitored approach to diplomacy has faced backlash from all political sides. Ukrainian President Volodymyr Zelensky and certain Russian state media have either criticized or commended Witkoff for mirroring Kremlin narratives.

Critics have also highlighted Witkoff’s lack of knowledge regarding the identities and backgrounds of the interpreters present during his discussions with Putin.

“He’s a nice guy, but a clumsy fool … he shouldn’t be handling this on his own,” a Trump administration official was quoted as saying by the New York Post.

Retired Army General Keith Kellogg, initially appointed as special envoy for the Russia-Ukraine conflict, has been re-designated as “special envoy for Ukraine” only, resulting in limited communication between the two leading U.S. negotiators, according to the tabloid.

“If Trump were truly committed to mediating an end to the war in Ukraine, he would appoint one person to negotiate with both parties through shuttle diplomacy, preferably someone with diplomatic experience,” former U.S. Ambassador to Russia Michael McFaul stated on X. “Witkoff is merely serving as a messenger for Putin. He’s not engaging in genuine negotiations.”

Following Witkoff’s latest trip to Moscow and warnings from the State Department about the possibility of the U.S. withdrawing from its mediation role in the peace talks, Putin suggested a 72-hour ceasefire to align with Russia’s Victory Day celebration on May 9.

Both Ukraine and the White House dismissed this proposal, advocating instead for a 30-day ceasefire agreement that U.S. officials introduced after discussions in March. Putin rejected that offer.