How Trump's top envoy bit off more than he could chew
Steve Witkoff, described as the 'everything negotiator', will fly to Oman on Saturday for talks with Iranian officials over Tehran's nuclear programme.
However, on Friday the 68-year-old met Vladimir Putin in Moscow to discuss the war in Ukraine, and has also been working on a hostage release deal in Gaza.
'Witkoff is involved in two other major talks [besides Iran] – he's constantly having to think about Gaza and the hostages, as well as Ukraine,' said Giora Eiland. 'He may be highly talented, but the nuclear issue is a highly technical matter.'
The retired major general, who often held high-level discussions on Iran's nuclear programme, added: 'It would also help to have experience of Iran's sophisticated and manipulative negotiating technique.'
Those close to Mr Witkoff – a former real-estate mogul whose biggest deal before his new role was the $632 million sale of New York's Park Lane Hotel – testify to boundless energy, hard-headedness and a deft touch for diplomacy.
In an interview with Tucker Carlson last month, the man who said he 'wanted to be' Donald Trump when the pair first met demonstrated a touch of imaginative sympathy possibly beyond the president.
You could talk to Hamas, Mr Witkoff said, when you realised its members 'wanted to live' and were not 'ideologically intractable'. He said: 'I believe they strap on the suicide vests onto young kids who don't know what they're doing.'
Even still, some of the progress that earned him the title ambassador at large has started to fade.
The ability to consider the position of each party in a negotiation is not the only one needed for a man in Mr Witkoff's shoes.
You also need time – lots of it – and expertise. Ukrainian officials were furious with Mr Trump's envoy when, in the same interview, he appeared not to know the names of the four regions recently occupied by Russia ('Crimea and Donbas' he said, referring to Donetsk, Luhansk, Zaporizhzhia and Kherson).
Defenders of Mr Witkoff argue his role is big picture, not obsessing over the details.
At times, Mr Witkoff, who is Mr Trump's golfing partner, has admitted to the challenges of his multi-faceted role. 'Maybe that's just me getting duped,' he told the Israeli news channel i24 of a moment when he thought Hamas had agreed to a deal.
He faces a challenge on Iran, with Mr Trump issuing a two-month deadline to secure a deal limiting Tehran's ability to construct a nuclear bomb. The UN mechanism allowing for the imposition of heavy 'snap-back' sanctions, from the 2015 Iran nuclear deal, expires in October.
Ahead of the talks, the president deployed at least six B-52 bombers to the Diego Garcia air base on the Chagos Islands. He has said he thinks 'Iran is going to be in great danger' if the negotiations fail.
Tehran has signalled that it is open to a deal, with Seyed Abbas Araghchi, the foreign minister, writing in the Washington Post that it could unleash a 'trillion-dollar' opportunity for US businesses.
However there are splits in the US national security team over what kind of agreement is needed. Some agree with Benjamin Netanyahu, Israel's prime minister, that only a full dismantling of Iran's nuclear programme is acceptable – and a military strike should follow if one is not forthcoming.
'There is an ocean of space between saying that Iran can't have a nuclear weapon and that Iran's nuclear programme must be 'dismantled' like Libya's. There is a risk that the US side, which currently lacks clear expertise and a defined endgame, will be out-negotiated by an Iranian side that has both,' Karim Sadjadpour, an Iran analyst at the Carnegie Endowment for International Peace, told the New York Times.
In his Carlson interview, Mr Witkoff spoke less ambitiously of a 'verification programme' to prevent Tehran from taking the final steps towards the bomb.
The envoy is not the first US official to regularly undertake 'whirlwind' diplomacy trips across the Middle East. Antony Blinken, the former Democrat secretary of state, regularly shuttled between Jordan, Egypt, Gaza and Israel.
But Mr Witkoff's peace-making agenda is wider still, and he appears to be operating more out on a limb as fears grow that a lack of experience and pressure from the White House could lead to unsatisfying outcomes across his portfolio.
At a meeting with Putin last month, he was kept waiting for several hours by the Russian president. On Friday, Dmitry Peskov, the Kremlin spokesman, downplayed any chance of a breakthrough in a brief interview. The meeting was largely an opportunity for Putin to share Russia's perspective and would take 'as long as the president needs', he said.
Margarita Simonyan, the editor-in-chief of Russia Today, described Mr Peskov as wearing a 'wide smile' as he talked to journalists.
Witkoff was criticised online for holding his right hand respectfully over his heart as Putin approached him. 'I liked him,' he said of Putin in his interview with Carlson, describing the Russian dictator as 'gracious to accept me'.
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