The Bronx real estate hustler who proves Trump is the boss from hell |
Welcome to Power Players, The i Paper’s new opinion series in which our writers and experts take an in-depth look at the key figures in American politics as the US reshapes itself and the world. • JD Vance will inherit Trump’s America in 2028. We still don’t know who he is• The radical philosopher inspiring Vance and Trump’s descent into despotism
Welcome to Power Players, The i Paper’s new opinion series in which our writers and experts take an in-depth look at the key figures in American politics as the US reshapes itself and the world.
• JD Vance will inherit Trump’s America in 2028. We still don’t know who he is• The radical philosopher inspiring Vance and Trump’s descent into despotism
“Well it was pretty silly but they thought they could strong arm us,” said Steve Witkoff, President Trump’s Special Envoy to the Middle East, offering a post-mortem on his own negotiations. “We went in there and tried to make a fair deal with them and it was very, very clear that was going to be impossible.” It hadn’t begun like this — with the failed negotiator pushing through a media round on Fox to justify the Iran war. But with hopes, suspicions and fears in every Middle Eastern capital, the New York real estate billionaire was on a speed-run to get Mr Trump a Nobel Peace Prize through an Iran deal.
I was working in the Foreign Office as a special adviser when Steve Witkoff first appeared on the scene. Had Trump really appointed some real estate pal of his to wrap up the Gaza War? There was a mixture of shock and scorn in the ranks at how this could possibly have come about. A few old hands predicted his time in diplomacy would be a failure. He’d fail to launch. But Witkoff kept on rising, as the Democrats levelled accusations he sought to enrich himself and the Trump family with fabulous real estate deals in Russia, even Iran, once he’d landed those prize-winning peace deals.
European diplomats are a bit like members of a guild. They join foreign ministries practically as children, straight out of university and spend their lives there, imbibing manners, traditions, techniques shaped by both this continent’s painfully remembered history and their historic buildings. Their prediction, almost to a man, was that Iran nuclear negotiations were so complicated — you could not afford a minute, let alone a whole term of amateur hour. They were right.
But let’s get back to the man. Witkoff is a self-made billionaire who grew up in 1960s Jewish Long Island, a golfing buddy of Trump who’d systematically played being a property lawyer, into a landlord, into a major real estate investor. A man with deep ties to Qatar, their prime minister even flew to his son’s wedding. Globalised, very. But very different from a diplomat.
Nobody could sum that gulf up better than Trump. “Steve’s a great dealmaker,” said the President last December. “He was a real estate guy in New York. He knew less about rivers and metes and bounds and Russia and the various places he’s working on. He knew nothing about it. But I recognised — for 20 years I’ve been dealing with everybody in New York, I said, ‘Steve’s got the best personality.’”
The first time I listened in to an official call with Witkoff, then only Special Envoy to the Middle East, I was struck by how utterly, utterly, different he sounded from the diplomatic world I had grown used to. This was no bullshit — or a lot of bullshit, it depends on the deal buddy — Bronx real estate talk. By the time I got to see him in the flesh in Paris, as a far-end-of-the-table extra in a few of the various Ukraine talks, I had the distinct impression that the diplomatic blob on King Charles Street had underestimated him. He wasn’t going away.
The first thing I learnt in politics about advisers or aides is there is only one question about them that matters. Can they actually speak for the boss? From Whitehall to the White House, the game in any political environment is about working out who has delegated power — and who doesn’t. The Gaza ceasefire, with Witkoff saying — no, no way, do it now — to Bibi Netanyahu was the first sign Witkoff did. He really did push the Israeli leader around.
This marked him out as different from the slew of other “envoys” Trump appointed after his inauguration. The East End-born Mark Burnett, the producer of The Apprentice, briefly inserted himself in UK-US diplomacy only to fade from view. Ric Grenell, vaguely titled as the envoy for Special Missions, bobbed along achieving little. General Kellogg, handed the Ukraine brief, lasted under a year. The reason: too far from his views, he couldn’t speak for the boss. But Witkoff, diplomats from Russia to Britain came to believe, could.
The Kremlin courted him: come to Moscow without the CIA, they said — seeking him out as the go-between. In fact, it was not just the Russians, but Putin himself doing the courting, seeking to seduce him as the route to a diplomatic triumph he could never achieve — after 1.2 million casualties — on the battlefield.
And so did we. The person in Whitehall who realised first just how important Witkoff would be was Jonathan Powell. Officials and politicians easily get hung up about “speaking to someone at their level”. The more insecure the politician, the more likely this is to come up. But the former 10-year Downing Street chief of staff turned all-powerful British national security adviser had no compunctions about talking to a mere “envoy”. And talking constantly. Feeding him ideas and analysis. Helping him work out the points in the negotiations he was manning where all sides could agree — or where to avoid. I felt the special relationship was becoming an abusive farce around me but somehow Jonathan Powell had docked like the perfect clever Athenian to the all-powerful Roman, as the Aeschylus-reading Harold Macmillan had imagined the relationship as a whole. His overriding aim was this: make him listen on Ukraine.
This is what was going on behind the scenes. Russia v Britain — in a battle of whispers in the ear. This has happened many times before: across post-colonial and Cold War contest-zones. But never quite like this in Washington. But what were we saying? This is the crux of it. Europe, based on intelligence and now years of invasion, is beyond convinced that this is not a war simply about territory, but the very existence of an independent Ukraine, whatever Putin might claim. Witkoff has approached it like a real estate deal. A question of territory. And so far, as a result, he has had no success.
The truth is that speaking for the boss isn’t the only thing that matters in politics when it comes to aides. The second thing I learnt to ask, once you’ve established that, is: can they actually get anything done? From the moment Witkoff was promoted to Special Envoy for peace missions in charge of handling Russia and Iran, the entire diplomatic world had been wondering this. Until this war began.
Over the winter, Witkoff was the man geopolitics was running through. As Trump boasted of assembling a “massive armada” in the Gulf, the largest US military build-up since the Iraq War, the dealmaker from Long Island found himself charged with pulling off a diplomatic trick that has defied 20 years of professional diplomats. A deal would have ended Iran’s nuclear programme, that was acceptable to Israel and the Washington hawks, while being face-saving enough for the mullahs. “The President is curious,” said Witkoff on Fox as the clock ran out. “I don’t want to use the word capitulated but why haven’t they capitulated.”
Landing a deal requires clarity of aims. Witkoff knows this of course. But as he handled the Iran file, three objectives got tangled and muddled in Trump’s rhetoric: a deal to end the nuclear programme, stopping Iran’s ballooning missile programme and – especially after the protests hit — full regime change. When I was in the Foreign Office and in the room at Europe’s own talks with the Iranians, I did feel there was a narrow path to a nuclear deal: one that would give Iran a token, face-saving amount of enrichment. But I was sceptical they’d fold on missiles which was what Israel truly worried about. And anyone can see regime change cut against any deal.
The fact is that Trump is not running an administration but a court — where the closeness and confidence of the king is key. A court where Bibi Netanyahu would turn out to be the greatest courtier. The rise of Witkoff was a story of taking on more and more for the boss. The truth is, in politics, that’s not always a good thing. Because when it goes wrong it’s suddenly all on you.
There was no grand deal to trumpet for Trump on Fox this week. Instead, Witkoff marched through making a series of nuclear justifications that will be pored over by Democrats, historians and journalists like Colin Powell’s at the United Nations on the eve of the Iraq War. Whatever happens now, Witkoff’s rise will never end at a Nobel gala night in Oslo. Instead his name will forever be linked to a cataclysmic failure of diplomacy. Then again, maybe it was always thus. No crying in the casino, as they say. One’s rise and success can easily turn into catastrophic disaster, with you owning the mess, if you play at the highest stakes on the world stage.
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