President Trump’s ambassador-at-large, Steve Witkoff, faces growing criticism for his inexperienced and ineffective approach to high-stakes negotiations with Russia, Iran, and Islamist terror groups. A former real estate investor with no diplomatic background, Witkoff now functions as Trump’s lead negotiator with Russian President Vladimir Putin and serves as special envoy to the Middle East. His solo meetings, reliance on Kremlin translators, and perceived alignment with adversarial narratives have sparked concern among Trump administration insiders and U.S. allies alike.
Witkoff greeted Putin “like an old friend,” according to reports, during a solo meeting where he lacked the typical U.S. delegation of advisors and translators. “Anybody engaging in these kinds of talks with Putin would benefit from having experienced Russia hands on his or her team,” said John Hardie of the Foundation for Defense of Democracies (FDD) Meanwhile, Putin brought senior aides Yury Ushakov and Kirill Dmitriev to the meeting.
Critics, including Ukrainian officials, believe Witkoff echoes Russian narratives. During a March 21 interview, he stated, “The largest issue in negotiations was political,” referring to Moscow’s claim to four Ukrainian regions (Donetsk, Kherson, Luhansk and Zaporizhzhia), but failed to recall their names. “Consciously or not, he is spreading Russian narratives,” Ukrainian President Volodymyr Zelensky said on April 17. While Former U.S. Ambassador to Russia Michael McFaul described Witkoff “as a mailman for Putin” who “is not negotiating anything.”
Diplomatic confusion extends beyond Russia. As special envoy to the Middle East, Witkoff attempted to broker an extended cease-fire between Israel and Hamas. On March 12, he left Qatar believing the terror group had agreed to release five hostages. Days later, Hamas countered with a drastically different offer. Witkoff admitted on Fox News, “Maybe that’s just me getting duped. I thought we were there, and evidently we weren’t.”
One member of the first Trump administration summarized the growing concern over Witkoff more bluntly. “Nice guy, but a bumbling f–king idiot,” they told the New York Post. “He should not be doing this alone.”
The Iran nuclear negotiations have also raised concerns. Witkoff’s initial approach largely mirrored that of the Obama-era Joint Comprehensive Plan of Action (JCPOA). The agreement, which President Trump previously referred to as possibly “the worst deal in history,” granted a pathway for Iran to eventually receive millions in sanctions relief and allowed for sunsets on several key restrictions.
Witkoff originally suggested a softer stance, proposing to allow Iran to retain its nuclear infrastructure. He took this position despite well-established evidence of Tehran’s past deceit and numerous treaty violations regarding similar nuclear infrastructure agreements.
Witkoff eventually reversed course after backlash, stating, “Iran must stop and eliminate its nuclear enrichment and weaponization program.” However, as Andrea Stricker of the FDD warned, “Iran may say that it’s permanent, but in effect, it would retain all its enrichment infrastructure.”
Shiri Fein-Grossman, a former Israeli security official, joined the rising chorus of White House insiders and foreign allies warning of the special envoy’s naïveté. “His assumption that actors like Hamas or Iran are primarily motivated by a desire to live… reflects a dangerous misunderstanding,” Fein-Grossman said.
Similarly, Danny Citrinowicz, an Israeli security expert and fellow at the Tel Aviv-based Institute for National Security Studies observed that Witkoff “is a good guy, but the Iran issue is so complex that I’m hoping he is bringing more people to the team… Because as of now the Iranians might have the upper hand, given their vast knowledge in negotiations.”
