Donald Trump's special envoy to Ukraine, Steve Witkoff, has become the target of intense criticism in Washington, with some detractors even branding him "Dim Philby" amid controversial peace negotiations with Russia.
The Leaked Calls Controversy
A five-minute phone conversation on 14 October between Witkoff and Vladimir Putin's foreign policy adviser Yuri Ushakov sparked outrage when it was leaked to Bloomberg News. During the call, the American envoy advised Moscow on how best to handle President Trump, suggesting they flatter his peace-making ambitions and praise the Gaza agreement while supporting a similar multi-point approach to ending the Ukraine conflict.
The leak prompted immediate calls from Trump opponents for Witkoff's dismissal, with many presenting the friendly tone as evidence that Trump has become a Kremlin puppet. Meanwhile, Russian officials blamed European powers for the leak, accusing them of attempting to derail potential peace agreements.
Business Background Versus Diplomatic Experience
Witkoff faces criticism on multiple fronts, beginning with his close personal and business relationship with President Trump. His lack of traditional diplomatic experience has alienated professional foreign service officers, while his failure to master Ukraine's war geography during an interview with conservative journalist Tucker Carlson earlier this year provided ammunition to his critics.
His involvement in Trump's Middle East peace efforts led to accusations that he was overstretched, and his several lengthy meetings with Putin - during which he notably refrained from describing the Russian leader as "Enemy Number One" - inevitably resulted in him being labelled a Putin stooge.
The Case for Witkoff's Approach
However, many charges against Witkoff can be viewed differently. His business-honed ability to understand perspectives from both sides of a negotiation could prove invaluable in delicate peace talks. Qualities displayed during his controversial Carlson interview - appearing open, affable, comfortable in his own skin, modest, humane and patient - may have contributed to his several-hour first meeting with Putin rather than the brief encounter many anticipated.
Witkoff appears to share with Trump the capacity to gauge how situations might appear from another party's perspective and adjust his approach accordingly. This doesn't make him a Putin apologist but rather a qualified negotiator who understands priorities on both sides of the conflict.
Another leaked call between Russian officials Ushakov and Putin's chief Ukraine negotiator Kirill Dmitriev discusses the genesis of a 28-point peace plan and claims officials from the US, Russia and Ukraine were all involved in the process. Though Dmitriev has called this leak "fake," it appears designed to establish Ukraine's involvement on record.
Both leaks coincide with news that Witkoff will travel to Moscow next week in a move widely seen as attempting to revive the stuttering peace process. Presenting him as too friendly with Russians and biased against Ukraine could weaken his negotiating position and discredit his mission before it begins.
The ultimate judgement of Witkoff's effectiveness may depend entirely on outcomes. If Putin rejects whatever terms appear in draft agreements and chooses to continue fighting, Witkoff will be remembered as a starry-eyed Putin sympathiser and diplomatic amateur. However, if his evident ability to communicate with Putin and his deal-making acumen foster the trust necessary for Moscow to make concessions, he may be credited with saving Ukraine as a sovereign state and countless lives.
