Steve Witkoff and his attempt to trade legitimacy for personal triumph

By Isabella Joseph

‘Ethical’ and ‘politics’ are two words that, when placed together, often feel oxymoronic – and President Trump’s special envoy, Steve Witkoff, has become the latest figure to reinforce that perception. In a leaked audio recording from October 14, Witkoff is heard, as many have argued, ‘coaching’ Yuri Ushakov, Putin's foreign policy adviser, on how to appeal to Trump regarding the Russia–Ukraine war and a potential peace deal between the nations. Treason? Hardly. Tact, perhaps – the supposedly standard method of a seasoned dealmaker, at least according to Trump himself.

The White House quickly defended Witkoff, insisting that nothing illegal had occurred. No documents were signed, and no policy was formally reversed. Yet the public outcry made clear that legality was not the issue. The offence was the catastrophic erosion of the legitimacy of US foreign affairs. Once again, the familiar banner of the ‘legal yet illegitimate’ was raised – a recurring theme in global politics.

As special envoy, Witkoff has made numerous visits to Russia and none to Kyiv. One might assume that such a glaring imbalance would alert the US administration to the absence of meaningful diplomatic engagement with Ukraine – unless, of course, the administration counts the Kremlin’s preferences among its own. The leaked audio revealed Witkoff advising Ushakov on how Putin and Trump should arrange a meeting ahead of President Zelenskyy’s visit to the White House. He suggested how the call should unfold and even recommended what some have described as ‘empty flattery’ to win Trump over. In retrospect, Trump’s staunch defence of this unsolicited meeting suggests he may have gained something far more valuable than any peace deal could offer: an enormous boost to his personal ego.

The Witkoff transcript confirms a troubling reality: the pursuit of personal triumph has become more valuable than upholding the principles of democratic diplomacy.

The diplomatic failure here was not a violation of statute, but a violation of good faith.

Privately, Witkoff laid out what he considered the necessary terms for a deal. In the recording, he states: “Now, me to you, I know what it's going to take to get a peace deal done: Donetsk and maybe a land swap somewhere.” This was an extraordinary concession. Ceding the Donetsk region would constitute a breach of Ukrainian sovereignty and would set a dangerous precedent: that territory seized through brutal force can be legitimised by international agreement. By entertaining this, the US risked signalling that territorial integrity – a cornerstone of the modern international system – is a negotiable asset in a personal bargain rather than an inviolable international principle. Such a move ensured that any resulting peace framework would be viewed as a hostile diplomatic ambush rather than a genuine negotiation. Even if Trump continues to defend the envoy’s behaviour, the mark of illegitimacy cannot be erased.

Although Ushakov later claimed that the leaked audio was largely fabricated, the damage was irreversible. The framework’s credibility collapsed entirely. The subsequent 28-point proposal, leaked on November 25 and described by Bloomberg as a Russian “wish list”, appeared to confirm suspicions that Kremlin aides had planned for Witkoff to present a Russian peace plan as a US initiative. Trump’s peace proposal unveiled on November 20 looked, in hindsight, like a mere compilation of Russian demands. Whatever hope remained for a credible peace process was effectively sabotaged.

Witkoff – a real-estate magnate turned envoy – treated nations and sovereignty as though they were assets in a zero-sum property deal. Ukraine’s worst fears were realised: an American envoy was assisting their adversary, undermining Ukraine’s willingness to negotiate and deepening scepticism about the credibility of Trump’s diplomatic team.

For President Zelenskyy, accepting a deal developed through such an illegitimate process would amount to political self-destruction. Witkoff did not shift Trump’s already transactional worldview; rather, he exploited it, leveraging the President’s vanity for the chance to deliver a high-profile diplomatic victory.

The core debate, then, centres on the legitimacy of Witkoff’s objective. For critics, his behaviour was a betrayal of democratic principles. For the administration, it was the ruthless pragmatism of a dealmaker. Was Witkoff a compromised agent, or a realist who believed that acknowledging Russia’s military gains was the fastest route to stopping the bloodshed? For those with a transactional mindset, peace achieved by any means – regardless of whose interests are served – is still peace. In Witkoff’s view, the choice was stark: allow the killing of Ukrainian civilians to continue, or forfeit just enough territory to halt further devastation.

Ultimately, a choice was made, and the US chose itself. The US often acts not as a neutral arbiter but as a dominant force that offers selective support. In collaborating with Russia, the administration aligned with the stronger partner. Though it sacrificed credibility on ethical grounds, it gained political expediency, securing the potential for a decisive personal win.

The Witkoff transcript confirms a troubling reality: the pursuit of personal triumph has become more valuable than upholding the principles of democratic diplomacy. By trading legitimacy for the prospect of a deal, the administration has ensured that any future agreement will carry the indelible stain of a cynical, self-serving transaction. Image: Heute.at