‘His Inexperience Shines Through’: Steve Witkoff Struggles to Manage Russia as Trump Peace Envoy
30th August 2025
Politico, a Voice of the Crust.
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.
What puzzles Politico is also what is ‘frustrating’ these apparatchik officials: They are used to people in government doing things The Way They’ve Always Been Done, and neither Trump nor Witkoff are meeting expectations.
This is a feature, not a bug. Doing things The Same Old Way is what got us into this situation in the first place. Trump (and Witkoff, who appears to be on the exact same page as Trump) is an entrepreneur; entrepreneurs don’t go for small incremental advances, but look for some way to achieve the Big Win. The way you do that is to try something, and, if that doesn’t work, try something else. If you do that often enough, you’ll finally hit the jackpot. Politicians and creatures of the Deep State aren’t looking for the Big Win; they’re looking to avoid the Big Loss (or, indeed, any loss at all that will impair their Peer Group Rating among the other apparatchiks).