Trump administration insiders are growing increasingly concerned over special envoy Steve Witkoff’s solo meetings with Russian President Vladimir Putin, the New York Post reported Wednesday, citing anonymous sources familiar with the matter.
Witkoff, a former real estate attorney and investor known as a “fierce negotiator,” has reportedly met with Putin four times since February without experienced diplomatic advisers or vetted interpreters, breaking with longstanding U.S. diplomatic protocol.
During their latest meeting last Friday at the Kremlin, Putin was joined by senior aide Yury Ushakov and Russian Direct Investment Fund head Kirill Dmitriyev. In a Kremlin video of that meeting, Witkoff can be heard asking if the one person sitting on his side of the table for discussions was “from the embassy.”
Initially appointed Middle East special envoy after Trump took office in January, Witkoff has since taken on an expanded role as ambassador-at-large, tasked with negotiating an end to the war in Ukraine.
His direct, unsupervised diplomacy has drawn criticism from across the political spectrum. Ukrainian President Volodymyr Zelensky and some Russian state media outlets have accused or praised Witkoff for echoing the Kremlin’s messaging.
Others have pointed to Witkoff’s unfamiliarity with the identities and backgrounds of interpreters present during his meetings with Putin.
“Nice guy, but a bumbling f***king idiot … he should not be doing this alone,” NYP quoted a Trump administration official as saying.
Retired Army General Keith Kellogg, who was first named special envoy for the Russia-Ukraine war, has been reassigned as “special envoy for Ukraine” only, leaving the two top U.S. negotiators with limited insight into each other’s discussions, the tabloid reported.
“If Trump finally got serious about mediating an end to the war in Ukraine, he would appoint one person to talk to both sides — shuttle diplomacy — and preferably someone with some experience in diplomacy,” former U.S. Ambassador to Russia Michael McFaul wrote on X. “Witkoff acts as a mailman for Putin. He is not negotiating anything.”
Following Witkoff’s most recent visit to Moscow and warnings from the State Department that the U.S. could pull back from its mediation role in peace talks, Putin proposed a 72-hour ceasefire to coincide with Russia’s May 9 Victory Day holiday.
Both Ukraine and the White House dismissed the idea, urging the Kremlin to accept a 30-day ceasefire deal that U.S. officials first proposed following discussions in March. Putin rejected that proposal.
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