Developer-turned-diplomat

The Hindu

24-05-2025

In November 2024, while appointing Steven C. Witkoff as Special Envoy to the Middle East [West Asia], U.S. President Donald Trump said that 'Steve will be an unrelenting voice for peace.' Since then, Mr. Witkoff, 68, in the words of an American analyst, has morphed from Trump's 'Middle East Envoy' into the 'Envoy of Everything'.
In less than six months, he managed to broker a ceasefire between Israel and Hamas (which has since lapsed), another ceasefire with the Houthis, got Russia to release a jailed American school teacher in a prisoner swap, persuaded Hamas to release an Israeli-American hostage, had Russia and Ukraine agree to resume truce talks, and got Iran back to the negotiating table over its nuclear programme, notwithstanding the fact that it was Mr. Trump who had scrapped a perfectly functional nuclear deal. That's an impressive run of achievements for any diplomat, let alone somebody with no formal diplomatic training and no background in international relations.
What explains his success? Admittedly, he works for a hands-on President who likes to do all diplomacy by himself. But that still doesn't account for his effectiveness, which might be rooted in how he bagged this gig in the first place.
At one level, it helps to be the President's long-time golf partner. It helps even more if you are a businessman from the same industry as the President (real estate), and both subscribe to its distinctive set of values — pragmatism, realism, and a belief that cracking deals and making money trumps all else, including ideology and abstract questions of right and wrong.
At another, Mr. Witkoff has trod the well-worn path of billionaire tycoons who begin by funnelling millions of dollars into a Presidential campaign, leverage their contributions to gain the candidate's confidence and influence within the party, and after their chosen horse wins the race, manoeuvre themselves into a position within or outside the administration from where they orchestrate a sweet convergence of interests between state policy and private business. They may do so with or without a formal role in the administration. Elon Musk is a prime example, and so is Witkoff.
However, unlike Musk and other megadonors of Mr. Trump, Mr. Witkoff is one of the few men outside the Trump clan who enjoys his absolute trust. It is this dynamic — he can pick up the phone and call the President any time — that sets Mr. Witkoff apart from other notional contenders for the role of one of the U.S.'s top diplomats, be they distinguished career diplomats or politicians with years of experience with the Senate Committee on Foreign Relations.
Mr. Witkoff's interlocutors — Vladimir Putin, Benjamin Netanyahu, Hamas — value the fact that they are negotiating with someone who actually speaks for the U.S. President and not another functionary from the State Department.
Such a high level of trust is not bought with financial contributions alone. It is earned over time. Mr. Witkoff's relationship with Mr. Trump goes back to the 1980s, when he was working for a law firm that handled Mr. Trump's real estate transactions. The story goes that Mr. Trump walked into a deli one day without his wallet, and Mr. Witkoff bought him a sandwich, launching a friendship that has served both of them rather well. Mr. Witkoff is on record saying that when he first met Mr. Trump, he wanted 'to be like him.' He acted on that impulse, transitioning from legal work to the real estate business, buying and selling property in some of the hottest markets, including Manhattan.
Mr. Witkoff has stood by Mr. Trump at critical times when many of his avowed supporters deserted him, such as after the January 2021 riot at the Capitol. He has testified on Trump's behalf in a civil fraud trial. Within the Republican Party, he has been Mr. Trump's prime trouble-shooter. Acting as Mr. Trump's emissary, he flew out to meet fellow Republicans who were not exactly fans of Mr. Trump. Mr. Witkoff negotiated with them — the likes of Georgia Governor Brian Kemp, Nikki Haley, one-time rival in the presidential race Ron DeSantis — and eventually lined them up in Mr. Trump's corner.
Mr. Trump and Mr. Witkoff believe that the negotiation skills and mindset that helped them crack complicated property deals are not only transferable to conflict resolution but are superior to the staid toolkit of traditional diplomacy. That partly explains Mr. Witkoff jetting off for one-on-one meetings — with aides or even translators — with Russian President Vladimir Putin, who he has met at least four times. It also explains the U.S.'s departure from protocol in talking directly with Hamas — something it has never done before. Ever the pragmatic deal-maker, finding Benjamin Netanyahu to be an obstacle, Mr. Witkoff simply bypassed him, which is how he got the American-Israeli prisoner freed when others had tried and failed.
Mr. Witkoff's desire to be the West Asia Envoy also needs to be seen in the context of his links to sovereign wealth funds from Gulf countries, including the Qatar Investment Authority, which bailed him out of a real estate deal gone wrong. The penchant for approaching geopolitical problems through the real estate lens found grotesque expression in Mr. Trump's idea, backed by Mr. Witkoff, that Gaza should be depopulated and redeveloped as a Mediterranean Riviera. It cannot be denied, however, that a conventional diplomat would have never approved the public airing of such an idea. As someone who both understands and shares Mr. Trump's vision, Mr. Witkoff's USP is his ability to market that vision to foreign interlocutors, but sans the Trumpian brashness, which could be fatally jarring in diplomatic realms populated by large yet fragile egos.