Jared Kushner and Steve Witkoff have spent the year attempting to negotiate with both Iran and Russia over wars that show no sign of ending. Kushner is Donald Trump's son-in-law and served as a senior adviser during Trump's first term in the White House; Witkoff is a real estate developer and a longtime friend of the president. Writing in a recent column for The Bulwark, Cathy Young does not mince words about the pair, branding them clowns.

According to The New Yorker, which published an extensive profile of Kushner, the Iran negotiations initially went well — until President Donald Trump's decision to begin bombing brought them to a close. It has been downhill from there. Iran, however, is not the only war in play.

Young also recalled Trump's 2024 campaign promise to end the Russia-Ukraine war "on day one." Russia launched its full-scale invasion of Ukraine in February 2022, meaning the fighting was already in its third year when Trump took office. Trump in fact said he could probably settle the conflict even before officially taking office. Seventeen months on, the promise remains unmet, and Trump continues to fall short.

Neither Kushner nor Witkoff, Young noted, has any experience as a diplomat or negotiator, and the inexperience has shown.

"It's safe to say that in the entire known history of diplomacy, there has never been a more clownish team of envoys than Witkoff and Kushner," the column said. "It's hard to find as much unanimity on anything in the Ukrainian media and among the independent Russian punditry as there is on this pair."

Young pointed to a "widely circulating sobriquet" for the duo — Vityok i zyatyok — "a pun involving a Russian nickname for 'Victor' and a diminutive for 'son-in-law.'" The wordplay is difficult to translate, but she said the sentiment is akin to calling the men "the Two Stooges."

Witkoff, Young wrote, embodies a "cluelessness and obsequiousness with Putin" that goes back long enough to be "legendary." "When we retire, we'll have all these incredible stories and incredible memories, and yours will be right at the top of it all," Witkoff told the Kremlin autocrat.

The envoys' most recent round of "negotiations" — a duo Young dubs "Tweedledum and Tweedledumber" — accomplished nothing on their latest trip to Moscow. They arrived with the same "peace proposals" and repeated the same recycled comments about "constructive" and "candid" conversations.

"However, most Russian-speaking observers noticed one richly symbolic detail," Young wrote. At one point during the visit, the envoys had dinner with Putin's special envoy Kirill Dmitriev at a Moscow restaurant whose exterior featured a large slogan: "EVERYTHING FOR VICTORY!" "It doesn't seem especially suggestive of a desire for peace," she observed.

The men also traveled to Ukraine. But after the trips, a report by CNN revealed that Cosmos 2573, an elite Russian spy satellite, was one of 14 Russian spacecraft tracking aircraft flying over Prince Sultan Air Base near Riyadh, Saudi Arabia — a facility that hosts U.S. forces — in the days before a major Iranian attack there. The finding suggests Russia has picked a side in the U.S. conflict with Iran — and it is neither Trump nor his close partners the Saudis. Instead, Russia appears to be feeding intelligence to Iran.

At a press conference alongside Ukrainian President Volodymyr Zelensky, journalist and television host Dmytro Gordon did not hold back when he pressed Witkoff about his meetings with Putin.

"Don't you think Putin has been lying to you all along" Gordon asked. "Don't you think that Putin, the Russians and Russia understand only one language — the language of strength? And finally, aren't you disgusted to sit at the same table with an international war criminal, a butcher of the Ukrainian people who is personally responsible for Ukraine's tragedy?"

Witkoff gave a non-answer.

Russian journalist Yevgenia Albats believes the administration's pivot back to the Russia-Ukraine war stems from its failure in Iran. "Trump desperately wants to score some points somewhere before the midterms," Young wrote, referring to the November 2026 midterm elections.

Young added that CIA Director John Ratcliffe may take over the negotiations, given that Kushner and Witkoff have failed in every respect. Meanwhile, Putin's confidence about the war may not rest on reality: in Young's assessment, his theories of eventual victory may be grounded in exaggerated battlefield reports — with recent Ukrainian counterattacks near Lyman a case in point.

Ukraine, Young concluded, faces a difficult winter ahead. But Russia's assumed momentum and Trump's diplomacy are far less formidable than they appear.