Russian President Vladimir Putin welcomes U.S. President Donald Trump's envoy Steve Witkoff during a meeting in Moscow, Russia August 6, 2025. Sputnik Gavriil Grigorov Pool via REUTERS
The global diplomatic goals of the U.S. used to be handled by a vast corps of skilled professionals, but under Trump, virtually all overseas goals are in the hands of one "witless" envoy, as James Ball wrote for The i Paper, possibly because he has a background "almost identical" to the president's.
Ball broke down Steve Witkoff's unlikely and alarming ascent in a scathing analysis from Wednesday. Initially chosen to oversee an Israeli ceasefire deal in Gaza, he was later upgraded to overseeing all missions in the Middle East, including brokering a deal to defuse tensions with Iran.
Now, he is also handling talks to end the years-long war between Russia and Ukraine. This high-stakes job has seen him make many alarming breaks from standard diplomatic procedures, such as meeting solo with Russian President Vladimir Putin and insisting that he trusts the Kremlin's English interpreters. These decisions overwhelmingly give Russia an upper hand, something Witkoff might not mind, Ball noted, as he has previously praised Putin and said that he does not "regard him as a bad guy."
"Is he amoral, or just incompetent?" Ball asked. "Usually, sensitive diplomatic negotiations are left to people with huge experience of the areas in which they operate. Typically, the lead negotiator has lived and worked in the region for decades, speaks the relevant languages, and has relationships with key power brokers in the various factions involved. They know the history, the resentments, the red lines. The hope is they can leverage that into the patient drudgework of diplomacy, dragging often reluctant parties over the line to a deal none of them will love, but that they can all live with."
Witkoff cannot meet that standard for all the missions he has been tasked with, Ball argued, because "No one on the planet has intimate experience of Israel, Gaza, Iran, Russia and Ukraine." That matter is made by the fact that the billionaire has had no diplomatic experience at all prior to his appointment as Trump's "Special Envoy for Peace Missions." The president, Ball suggested, seemed to pick him because of their strikingly similar professional backgrounds.
"His background is almost identical to Trump’s – Witkoff is a billionaire who made his money through real estate deals," Ball explained. "His portfolio is even more U.S.-focused than the President’s, and the handful of major deals his company closed outside the U.S. were in London. Witkoff knows the world of US real estate, and little else."
With "the witless Witkoff" now handling the Russia-Ukraine peace talks between Russia and Ukraine, Ball wrote that Trump has made him all of Europe's problem, with no regard for the consequences of his failure.
"It is Ukrainians first, and then Europeans, who will pay with their lives if Witkoff screws up," Ball wrote. "Americans will sit a continent away and pretend it’s not their problem if it blows up in their faces."