Trump Envoy Steve Witkoff Criticised Over Iran, Hamas, Russia Strategy

The role of Steve Witkoff, the US special envoy to the Middle East, has come under massive scrutiny, with many foreign policy experts and analysts questioning his ability to effectively engage with geopolitical players such as Iran, Hamas and Russia.

Mr Witkoff has also become Donald Trump's primary liaison to Russian President Vladimir Putin. His attendance at high-level meetings with Russian officials without the support of a traditional diplomatic team has also left several people within the government astonished, according to a report by The New York Post on Wednesday.

During a meeting with Mr Putin last Friday, Mr Witkoff appeared alone, lacking the usual diplomatic or military advisers.

"Anybody engaging in these kinds of talks with Putin would benefit from having experienced Russia hands on his or her team and bringing them along to meetings with the Kremlin," John Hardie, director of the Russia programme at the Foundation for Defense of Democracies, told The New York Post.

A former Trump official didn't hold back, calling Mr Witkoff a "nice guy," but totally unqualified for the role. “Nice guy, but a bumbling f***ing idiot,” he said of Mr Witkoff.

Mr Witkoff's efforts to broker a ceasefire between Israel and Hamas initially saw some success when he helped pause hostilities for two months. But a subsequent attempt to extend that agreement collapsed. After a meeting with Hamas officials in Qatar on March 12, Mr Witkoff believed he had secured a deal that included the release of five living hostages in exchange for Palestinian prisoners.

Days later, Hamas altered the terms, offering only one living US hostage and four bodies - a proposal Mr Witkoff rejected, reported The New York Post.

Concerns about Mr Witkoff's competence reportedly stemmed from his statement in a Fox News interview on March 23, where he said he believed the US secured a one-month extension of the ceasefire on the previous hostage agreement. "I thought we had an acceptable deal," he said, as per Jerusalem Post.

Critics say Mr Witkoff's lack of diplomatic training may be clouding his judgement, especially in contexts requiring cultural and ideological understanding.

Shiri Fein-Grossman, former Head of Regional Affairs at the Israel National Security Council, said that Mr Witkoff's belief that "actors like Hamas or Iran are primarily motivated by a desire to live" shows a misunderstanding of their "ideological goals."

Some observers question the wisdom of assigning both Russia-Ukraine and Iran-Hamas dossiers to one individual.

Israeli security expert Danny Citrinowicz questioned how Mr Witkoff manages the "demanding negotiations" with both Iran and other parties. He expressed concern that the complexity of the Iran issue may require a larger team for effective handling.

Russian state media has taken notice of Mr Witkoff's tendency to echo Putin's rhetoric. During a March 2025 interview with Tucker Carlson, he adopted Moscow's language, referring to occupied Ukrainian regions as "so-called four regions" and claiming the residents overwhelmingly voted to be part of Russia. Ukrainian officials were quick to rebuke these claims.

As far as Iran is concerned, after indirect talks in Oman, he suggested letting Tehran keep its nuclear facilities as long as it agreed to low-level enrichment. The following day, however, he changed his mind and said that Iran's enrichment programme had to be fully dismantled.

Experts remain unconvinced though, with former National Security Advisor John Bolton stating, Mr Witkoff's "discussions with Iran are a waste of oxygen."