Concerns Rise Over Witkoffs Unmonitored Encounters with Putin, Breaking Diplomatic Norms

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

Witkoff, a former real estate lawyer and investor recognized for his aggressive negotiation style, has allegedly met with Putin four times since February without the presence of seasoned diplomatic advisors or approved interpreters, departing from established U.S. diplomatic practices.

During their most recent meeting last Friday at the Kremlin, Putin was accompanied by senior aide Yury Ushakov and Kirill Dmitriyev, the head of the Russian Direct Investment Fund. A Kremlin video of this encounter reveals Witkoff questioning whether the sole figure seated next to him at the table was «from the embassy.»

Initially designated as the Middle East special envoy when Trump assumed office in January, Witkoff has since been given an expanded role as an ambassador-at-large, responsible for negotiating an end to the conflict in Ukraine.

His direct and unsupervised diplomatic efforts have faced criticism from various political factions. Ukrainian President Volodymyr Zelensky and certain Russian state media have either accused or commended Witkoff for reflecting the Kremlin’s narrative.

Additionally, some have highlighted Witkoff’s lack of familiarity with the identities and backgrounds of the interpreters who have been present during his meetings with Putin.

«He’s a nice guy, but a total mess … he shouldn’t be handling this alone,» the New York Post quoted a Trump administration official as saying.

Retired Army General Keith Kellogg, who was originally appointed as special envoy for the Russia-Ukraine conflict, has been reassigned to focus solely on Ukraine, which has left the two leading U.S. negotiators with limited visibility into one another’s discussions, according to the tabloid.

«If Trump were genuinely serious about mediating an end to the war in Ukraine, he would appoint one individual to communicate with both sides—shuttle diplomacy—and ideally, someone with experience in diplomacy,» former U.S. Ambassador to Russia Michael McFaul stated on X. «Witkoff is merely delivering messages for Putin. He isn’t negotiating anything.»

Following Witkoff’s latest trip to Moscow and the State Department’s warnings about a possible withdrawal from its mediation role in peace negotiations, Putin suggested a 72-hour ceasefire to coincide with Russia’s Victory Day holiday on May 9.

Both Ukraine and the White House dismissed this proposal, urging the Kremlin to accept a 30-day ceasefire agreement originally suggested by U.S. officials after discussions in March, which Putin promptly rejected.