Witkoff's Fading Star

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“I don’t regard Putin as a bad guy”. So said Trump’s Special Envoy to the Middle East turned Russia pointman, Steve Witkoff, in a recent appearance on The Tucker Carlson Show in which he spoke at length about a rollercoaster two months of shuttle diplomacy that has taken him to Qatar, Gaza and Moscow. Witkoff’s rise to become one of America’s top diplomats has been meteoric and impactful, and is both a cause and an effect of a major reset in US foreign policy that has shunned traditional allies and brought old antagonists such as Russia in from the cold.

Witkoff’s Interview on Fox News

So who is Witkoff, and why does his political ascendancy matter? 

Witkoff, like Trump, made his fortune in the world of Manhattan real estate. He started out as a real estate lawyer, before founding real estate investment firm Stellar Management in 1985. After successfully investing in a number of lower price residential and office developments in the city, he started the Witkoff Group in 1997, which went on to acquire high-profile assets such as the Woolworth Building and Park Lane Hotel. Forbes estimates that Witkoff is now worth at least $1bn. 

The Woolworth Building in New York City

It is reflective of Trump’s view of the world that he has picked a real estate mogul to be his lead international negotiator. The president is of course himself a real estate guy, and he has come to understand geopolitics in transactional terms, under which parties pursue their own, narrow material interests and think in the timeframe of closing a deal, rather than creating a long-term settlement. It is also reflective of Trump’s lack of interest in expertise or detail when making these appointments or trying to negotiate with America’s partners and adversaries. 

Early Wins

But despite his lack of diplomatic experience, Witkoff got off to a strong start, scoring some big wins in his first few weeks.

Before the Trump administration was even inaugurated, he was in Qatar negotiating with Hamas representatives, resulting in the agreement of a truce between Israel and Hamas under which strikes on Gaza were paused and hostages were handed back. During a conflict that has seen an estimated 50,000 Palestinians killed and in which both sides have strong incentives to keep fighting, this is a real achievement. 

Witkoff was, according to reporting in non-partisan, non-US news outlets, a positive force in the agreement. Financial Times sources credited him with breaking the deadlock around US negotiations  with Netanyahu, forcing talks and outcomes where Biden’s officials had been given the runaround.

He also scored an early win on Russia diplomacy too, travelling to Moscow and securing the release of Marc Fogel - a US citizen serving a 14-year jail sentence in Russia for possession of medical marijuana  - in exchange for Alexander Vinnik, a Russian crypto entrepreneur facing money laundering charges in the US. 

Marc Fogel

However, just over two months into the new administration, things are looking decidedly less rosy. The Israel-Hamas ceasefire has unwound after negotiators failed to agree a second phase, with Israel resuming strikes on Gaza on 18 March, killing more than 400 Palestinians. 

Blaming Hamas for failing to honor its commitments, Witkoff told Fox News: “I thought we had a deal, an acceptable deal. I even — I even thought we had an approval from Hamas, maybe that’s just me getting — getting, you know, duped”. That Witkoff considers himself to have been “duped” by Hamas suggests that he failed to understand what their underlying demands and motives actually are, instead relying on their word rather than a sober assessment of the conflict’s drivers. 

In Witkoff’s defence, he is unable to overcome the internal politics in Israel that prolong the conflict. Netanyahu’s political position is precarious: he has been dependent on restive, far-right coalition partners to pass a budget last week in order to stave off fresh elections that could see him removed from office and facing long-running corruption charges.

Advantage Putin

However, it is Witkoff’s statements on Russia and Ukraine that should really lead Americans to question his judgement and qualification for the role. In his wide-ranging conversation with Tucker Carlson, Witkoff appeared sincere but bereft of detail. He stumbled over Ukraine’s geography, and was only able to name two of the Ukrainian regions currently claimed by Russia, Crimea and Donbas, before Carlson helpfully gave him a third (Luhansk, which he revealingly pronounced as the russified “Lugansk”). These are not minor oversights - they have been major points of contention between Moscow and Kyiv since 2014. His difficulty naming them points to an extremely broad brush approach to the conflict that likely ignores the real complexity of the situation. 

Tucker Carlson and Steve Witkoff talk geopolitics

More surprising still is that he appears to have taken on Russian talking points since his meeting with Putin. When discussing the contested regions in Eastern Ukraine, he seemed to push the Kremlin narrative that they were legitimately part of Russia, saying that: “They are Russian-speaking, and there have been referendums where the overwhelming majority of the people have indicated that they want to be under Russian rule”. It is a sign of how far American foreign policy has moved under Trump that referenda held by the proxies of an authoritarian invading power are considered valid or meaningful. 

Beyond parroting Kremlin lines on the Russian language and the so-called referenda in eastern Ukraine, Witkoff seems to share the Europe-scepticism of other high profile members of the Trump administration like Pete Hegseth and JD Vance. When Tucker Carlson asked him about the UK’s plans for an international force to support a ceasefire in Ukraine were “posture” and an attempt to “be like Winston Churchill”. 

This incredulity toward what would be one of the main stakeholders in any plausible peace agreement raises renewed questions about how balanced the Trump administration’s approach to resolving the conflict is. As we’ve written before, Zelenskyy likely understands that the era of blank cheque US taxpayer support is over, and that some kind of reciprocal financial arrangement with Washington will be needed to reset the political narrative about American support for Ukraine. But the perception that the US is railroading Kyiv, London and Brussels in some kind of backroom deal with Putin is a major obstacle to creating a viable peace in Ukraine. This is not adept diplomacy. 

Witkoff is, of course, handcuffed by the whims of his boss, and is not empowered to decide US foreign policy independently of the White House. However, his apparent gullibility towards America’s long term adversaries and disregard for its allies makes for a weak negotiator who will struggle to resolve the major conflicts sitting in his intray. If Trump wants to win a Nobel Peace Prize, he has picked the wrong guy for the job.