The U.S. administration has expressed disappointment over the way President Donald Trump's special envoy for the Middle East, Steve Witkoff, is conducting talks with Russia, according to a report by the New York Post.

Witkoff, who represents Trump’s interests in the Middle East, is also involved in direct communication with Russian President Vladimir Putin. According to insider sources cited by the newspaper, Witkoff has been attending high-level discussions alone and has, on occasion, relied on translators provided by the Kremlin—an unusual approach that strays from standard diplomatic norms.

During his most recent meeting with Putin, which took place last Friday, Witkoff greeted the Russian leader warmly, referring to him as an old friend. Notably, he arrived without the usual entourage of advisors, experts, and military personnel that typically accompany American officials at such negotiations, the article states.

Putin, on the other hand, was joined by his aide Yuri Ushakov and the head of the Russian sovereign wealth fund, Kirill Dmitriev.

"Anyone engaging in dialogue with Putin would benefit from having a team of seasoned negotiators at their side," said John Hardie, director of the Russia Program at the Foundation for Defense of Democracies.

A former Trump administration official was more blunt in his assessment of Witkoff’s solo efforts:

"He’s a nice guy, but clumsy as hell. Honestly, it’s foolish for him to try doing this on his own."

"Maybe I'm Just Being Misled"

The article points out that as Trump’s special representative to the Middle East, Witkoff had attempted to broker a ceasefire and secure the release of hostages between Israel and Hamas—a mission that ultimately fell through.

In Israel, observers have criticized Witkoff’s lack of diplomatic background and his tendency to take on too much at once.

"How does Witkoff divide his focus between two of the most critical sets of negotiations? I think he means well, but dealing with Iran alone is such a massive task that I sincerely hope he’s bringing in more people to help," commented Danny Citrinowicz, a security analyst at Tel Aviv's Institute for National Security Studies.

Two Negotiators Instead of One

According to the piece, Trump has designated two separate special envoys to handle issues concerning the Russia-Ukraine war. In addition to Witkoff, retired General Keith Kellogg serves in a similar capacity. Initially tasked with overseeing both Ukraine and Russia, Kellogg later transitioned to focusing solely on Ukraine, leaving Russia-related matters to Witkoff. The article notes that this arrangement has made managing negotiations more challenging.

"The main issue with how President Trump split duties between Witkoff and Kellogg is that Witkoff, who has better access to Trump, tends to relay Moscow’s perspective while having little sway over viewpoints from Kyiv," Hardie said.

Former U.S. Ambassador to Russia Michael McFaul offered his own critique, suggesting that the situation calls for a single, experienced negotiator.

"If Trump were truly serious about mediating an end to the war in Ukraine, he’d appoint one person to serve as a go-between for both parties. Someone well-versed in diplomacy. As it stands, Witkoff functions more as Putin’s mailman than an actual negotiator," McFaul remarked.

Witkoff's Interactions with Putin

As previously reported by UNIAN, during Witkoff’s latest visit to Russia on April 25, Putin discussed the potential resumption of direct talks with Ukraine. Yukio Ushakov, Putin’s assistant, described the conversation as constructive and "quite useful." They reportedly explored the idea of restarting bilateral peace negotiations between Moscow and Kyiv.

McFaul continues to maintain that Witkoff has failed to make any progress toward a ceasefire in Ukraine and should be replaced by a more experienced diplomat. He noted that even the most skilled negotiator would struggle to manage multiple international conversations simultaneously, stressing that Witkoff should focus solely on one region.

Recently, Witkoff spoke publicly about his dealings with Putin, boasting of four meetings with the Russian leader. He emphasized that none of the sit-downs lasted under three hours, with one reportedly stretching to "almost five hours."

Other News You Might Find Interesting:

• Trump Administration Approves First Weapon Sales to Ukraine – Kyiv Post

• Rubio Calls Mineral Deal “A Step Toward Ending the War”

• Tesla Board Reportedly Seeking New CEO to Replace Musk – WSJ