Our new book is The Comeback: The 2024 Elections and American Politics. The second Trump administration is has been full of ominous developments.
President Donald Trump’s surprise Anchorage summit with Russian President Vladimir Putin could have been a signature achievement for Steve Witkoff, the developer-turned-diplomat who facilitated the meet up.
But promised follow-up meetings between Putin and Ukrainian President Volodymyr Zelenskyy have not materialized, ceasefire demands were dropped, threats of tough action have disappeared and Trump’s team has offered no clear road ahead.
Some frustrated U.S., Ukrainian and European officials say part of the problem is the go-it-alone style of Witkoff, Trump’s special envoy for peace missions and go-to negotiator on Ukraine. He has refused to consult with experts and allies, leaving him uninformed at times and unprepared at others, according to seven people familiar with internal discussions. Two said he misses the mark by viewing the conflict through a real estate lens, like a land dispute.
Trump’s unconventional fixer has met Putin five times over six months, but he has yet to translate his access to the Russian leader into any breakthroughs on Ukraine....“His inexperience shines through, he has the president’s ear, which is evident, but there has been some confusion about what has been said and agreed,” said a person familiar with the diplomatic effort.
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“He’s kind of a rogue actor,” said a U.S. official familiar with Witkoff’s diplomatic style. “He talks to all these people, but no one knows what he says in any of these meetings. He will say things publicly but then he changes his mind. It’s hard to operationalize that.”
Witkoff’s Washington office is sparsely staffed, and short on people with Russia expertise or experienced in complex diplomatic negotiations. And he has refused to do typical consultations with Russia and Ukraine experts in and outside of government, according to the five people familiar with internal discussions.
Like Ellis in Die Hard, he thinks he’s a clever negotiator but he has no clue that he’s dealing with a stone killer. https://t.co/UkmpjDcqJI
— Jack Pitney (@jpitney) August 18, 2025
