Steve Witkoff catapulted himself to the billionaire club with a combination of gumption and charm. Credit: Getty
Stephen Witkoff, President Trumpâs Middle East envoy, might be a fresh face for followers of world affairs. But for students of New York real estate, heâs an old familiar presence. The 67-year-old has been buying, leasing, selling, and modifying buildings in the Big Apple for more than 30 years, catapulting himself to the billionaire club in the process.Â
Investing as the head of the Witkoff Group, he has been updating classic Manhattan office buildings like the Woolworth tower and creating luxury condominium high-rises like 111 Murray Street. Even today, his son Alex is rescuing One High Line â the pair of angular Bjarke Ingels-designed waterfront towers in West Chelsea â from an ignominious fate as the misbegotten condo development of a collapsed investing group.
Along the way, Witkoff has built a reputation for a high risk tolerance that suits Trump as the two of them seek to settle the ultimate real-estate dispute: namely, the Israeli-Palestinian conflict. The prize is unquestionably attractive. Yet given the stakes and the sensitivity of the region, Gotham-style real-estate wrangling could also prove disastrous.Â
Witkoffâs journey to the world of high diplomacy began, of course, in his friendship with fellow developer Trump. Indeed, so close are the two men that Witkoff was on the golf course at Mar-a-Lago last year when a second failed assassination attempt was made on Trump. According to a New York real-estate source, who declined to be identified because he didnât want to get involved in Trumpian affairs, Witkoffâs grandson was named Donald after his grandfatherâs friend, the president. And Trump attended Alexâs bar mitzvah reception, the person said.
Trump rewarded Witkoffâs personal loyalty by naming the latter his envoy to the Middle East. When it comes to the bedeviling region, Trump has from the beginning thought outside the box. Witkoffâs position is roughly the same as that of Jared Kushner â Trumpâs son-in-law, also a major figure in New York real estate â in the first term. Despite just about no previous experience as a mediator, Jared, son of real-estate mogul Charles Kushner, produced the Abraham Accords that opened diplomatic relations between the Jewish state and four Arab states: the United Arab Emirates, Bahrain, Morocco, and Sudan.
Kushner sees the Middle East as a real-estate opportunity â albeit, one in which the main hazards arenât so much New York regulators withholding construction permits as Islamist groups and states that periodically go boom. Kushner parlayed his position in the first Trump administration into the leadership of Miami-based Affinity Partners, an investment firm which he founded and which has been raising investment capital largely from Middle Eastern companies â $3.1 billion as of October, to be exact, according to a Wall Street Journal story.Â
Witkoff brings a similar mentality to the region. Although Witkoff, like Kushner, lacks previous diplomatic experience, he does have an international cast of friends and contacts, in the Middle East and around the world. A longtime associate in New Yorkâs real-estate industry calls him an âexcellent negotiatorâ.
Despite nominally serving as the presidentâs ears and mouth in the Middle East, Witkoff was also dispatched to Moscow to negotiate the release of Marc Fogel, a teacher who had been held in prison for three years on marijuana charges. Witkoff is also part of the negotiating team seeking to end the Russia-Ukraine war, over and against Ukrainian President Volodymyr Zelenskyyâs objections and others who warn that the Trumpians are ignoring Kyiv. Witkoff is unperturbed by such talk. In a news conference shortly after Fogelâs release, he described his role this way: âHe [Trump] asks, and we say yes.â
Witkoff, in his light brown overcoat and perfectly starched collar, has become a fixture of television news as he represents the Trump administration globally. Itâs a long way from the days in the early Nineties, when he used to personally collect rent, while carrying a gun, from his tenants in The Bronx, and where he got his start in the business.
Born in 1957 in The Bronx, he graduated from Hofstra Law School on Long Island in 1983. Afterwards, he landed a job with the real-estate law firm Dreyer & Traub, where one of his clients was none other than … Donald Trump. He then formed a partnership with the late Laurence Gluck that was known as Stellar Management (the âSteâ in Stellar stood for Steve, and the âLarâ part stood for Larry).Â
Although their business and political paths have long overlapped and even converged, Witkoffâs approach to real estate differs from Trumpâs. While Trump built his brand around showy towers, resorts, and golf courses, Witkoff followed a more tried-and-true path through commercial and residential real estate, keeping a low profile and letting his bank accounts do the talking.
Even so, Witkoff would gain a measure of notoriety that few real-estate investors achieve. He moved fast in the business, blowing his way past the stodgy families headed by scions three or four generations removed from the enterprising paterfamilias. He was a scrappy hustler determined to build on his early successes. It helped that this was the Nineties, when commercial real estate had been beaten down by the savings-and-loan scandal, which led to the bankruptcy of several small banks that had a large number of failing new properties on their books. Those who bought low were richly rewarded. Witkoff was one of them.
He was fortunate, too, to have in his corner a financier named Andrew Stone of Credit Suisse First Boston. Stone â who viewed himself as the âStar Trek lenderâ, boldly lending where others on Wall Street wouldnât â made bets on up-and-coming real-estate entrepreneurs who showed the ability to spot properties with the potential to bring in enough money to achieve well over their debt service. Besides Witkoff, Stone backed Trump, the developer Harry Macklowe, hotelier Ian Schrager, and the post-Soviet fertiliser king-turned-development mogul Tamir Sapir, among others.
What set Stone apart from most financiers in his position was his willingness to underwrite as much as 97% of a commercial real-estate purchase. That can be deadly if the property doesnât lease up â if it fails to find enough tenants willing to pay a premium for the quality and location. But if it does lease up, the owner can amass untold riches. Hence, Witkoffâs reputation for high-risk, high-reward deals.
Besides the famed Woolworth Building, designed by celebrated architect Cass Gilbert, Witkoffâs portfolio at one time included the Daily News Building on East 42nd Street, which the tabloid long ago abandoned, and 33 Maiden Lane downtown.Â
âHe can be tough when he needs to be tough, and he can be charming when he needs to be charming,â said Jonathan Mechanic, chairman of the real-estate department at the law firm Fried Frank and a key figure in New York commercial real estate. âAlthough Iâm not sure I would have seen this coming 20 years ago. I have no doubt that he can feel comfortable talking to anybody at any time.â
Mechanic recalled joining Witkoff at a meeting with Goldman Sachs on the financing of the Daily News building. Witkoff âhad been up in The Bronx, and he had his gun attached to his ankle. When he leaned forward, and the gun could be seenâ. Aware of the impression heâd made, Witkoff vowed to âcome a little lighter afootâ next time.Â
Whether this combination of gun-toting gumption and charm can bring peace to the Middle Eastâs warring factions is a different question. As it is, Americaâs Arab allies have been left unnerved by Trumpâs brainstorm for removing Gazaâs population to develop the territory into a sort of Middle East riviera. At stake is nothing less than the expansion of the Abraham Accords to include what once was unthinkable: formal relations between Israel and Saudi Arabia.
High risk, high reward, indeed.
I presume that Mr Witkoff like Mr Blinken before him is a Jew, and therefore it is rather unlikely that the Arabs will listen to him.
I am surprised that Mr Trump didnât choice a more WASP type character who could at least speak with the âvoice of authorityâ.
Kushner, also a Jew, negotiated the Abraham accords
That went well and solved a lot!
Sabotaged by Biden/Blinken sucking up to Iran.
And topped off by Hamas, enabled by their leftwing backers in October 2023
The Abraham Accords were purely about business, economic, and financial connections, with no involvement in governance, state formation, or peacemaking like the Camp David Accords. There was not even Palestine issue on it.
It’s crucial to distinguish between agreements that establish states or governance structures and those that focus solely on economic and business ties. Kushner could not even understand the issue at face value so he focused what he knew – how to make financial connection with already allies that had established relations with US.
The genius of the Abraham Accords was that they negotiated peaceful normality and diplomatic relations between the Arab states and Israel, bypassing the Palestinians. There are now Jewish/Israeli communities living in the UAE – unthinkable only a few years ago.
The ‘state formation’ you reference comes under Einstein’s rubric that the definition of insanity is doing the same thing that doesn’t work again and again. The Accords brilliantly work round this.
Yes, that is what the Abraham Accords did. However, because Netanyahu refused to cut a deal that would have given the Palestinians a reason not to fight, the war goes on, and the Abraham Accords are in jeopardy. (There is a tape circulating where Trump is lambasting Nutty for this).
We haven’t had peace since 47-48, only lulls in the fighting, because the Pals have never been given a reason to put down the gun. Unless they are exterminated, there will be no peace without justice. Any attempt to truly impose the “final solution” will cause every regiem in the region to collapse and likely bring WW3 to the world.
I’m backing Trump, because he knows this and Nutty boy is going to dine on some serious crow.
Are you suggesting hiring decisions need some considerations of DEI?
Certainly not.
I believe you are confusing modern Arab diplomats of the modern Arab world with the blood thirsty throw-backs to the 3rd century. No other Arab country gives a hoot about the depraved, barbaric radicals who currently occupy the large parking lot that is Gaza. Only purple-haired, septum-pierced, young, white overweight females seem to care.
You mean the ICC?
Total parking lot eh?
You know they are there because they were kicked off more fertile land close by right? And who made it a parking lot? It was a prison before it was a parking lot.
Yes, only the purple haired care about what is happening. Plus the ICC, the whole of the UN, bar USA and Micronesia.
Moron.
It would seem to me that only the followers of Islamicism and Zionism care about racial/religious identities. Mammon is the true God that most follow.
Or as Heraclitus put it so eloquently: âWar is the father of all and the King of allâ.
This article doesnât really tell us anything, except Trump has appointed a mate who developed property to a position of government
It tells us that Trump is pursuing the policy of his first term, a one state solution in Israel and Palestine where everyone will have equal rights.
Theyâre going to give those Palestinians in Gaza and the West Bank the right to vote for representatives in the Knesset?
Remember that some are more equal than others!
It tells us that this is an administration of deal makers versus policy wonks (who usually get nothing done) – remember Hillary Clinton exclaiming she has dozens of âpolicy papersâ on her campaign website!!!
Duplication.
You have to acknowledge, all else has failed and Trump is prepared to try something different.
Bringing in commerce is a brilliant move, the Arabs understand commerce and they won’t let politics get in the way of a good deal
I doubt that even Witkoff & Trump can cajole the Arab countries into taking the Gaza Palestinians. No one wants them.
Said Michael about the Jews in late nineteen thirties early forties Europe.
No one wants them.
Why should anyone be in the position to âwantâ them? They live there. They have had their land stolen. They have been moved. They have seen women and children murdered by a colonising people.
Moron.
Am I the only one here to find it morally utterly repugnant to talk about the future of millions of people as a ‘real estate deal’?
Similar to discussion on the future of Ukraine as how much money it could make for the USA if they surrendered to the murdering rapists of the Russian state?
Whatever works. Moral stance is awesome and greatly satisfying though
You probably are, most people real estate is the very essence of a country and it’s people.
But you carry on virtue signalling and let those like the people of gaza and ukraine continue to suffer.
‘Most people’ do not own real estate. If you think that property is the ‘very essence’ of anything other than a love of and worship of mammon then I pity you. If loathing of ethnic cleansing to make money from real estate deals is ‘virtue signalling’ then so be it.
This article reads as a flattering piece on Witkoffâa common form of promotional journalism meant to shape public perception and build an identity around a figure. It is essentially a belief-building exercise. However, most readers engaged with this topic already have some understanding of the issues and of Witkoff himself. What the article sidesteps is the core reality: the Israeli-Palestinian conflict is fundamentally about land and people, not economics or finance. It is a question of statehood versus statelessness.
Framing the conflict in economic terms is an ideological and idealistic approach that may resonate with Western audiences but has little relevance in actual negotiations. In the Middle East, where real decision-making happens, this language is not even part of the conversation. Western discourse relies heavily on scripted narratives, whereas Islamic legal and political thought is non-binary and principle-based. This means that discussions about infrastructure or investment projects will remain secondary at best. The real conversationsâones Western audiences are unlikely to accessâwill focus on sovereignty, borders, and governance.
It is crucial to recognize that Western media primarily functions to shape public narratives, not to reflect the material reality of high-level diplomatic discussions. The laws and policies of Islamic nations, such as Saudi Arabia, are structured around overarching principles rather than reactive policymaking. Negotiations concerning Israel and Palestine are not driven by economic incentives but by fundamental questions of land, people, and sovereignty. Until those issues are resolved, discussions about development will be meaningless. Anyone attempting to introduce such topics in serious negotiations would likely be dismissed outright.
With this in mind, it is essential to read these articles critically and distinguish between what is crafted for public consumption and what is actually happening on the ground. For your own understanding, separate what is said on TV to project confidence from the real geopolitical maneuvering, which will not have figures or financial deals attached.
The Israeli-Palestinian conflict has persisted for over 80 years, with multiple opportunities for resolution that never materialized. At any moment, Israel and Palestine could fall into a trap, where external powers impose a resolution based on broader geopolitical pressures â because again it is state making not investing. In this sense, it parallels Ukraineâs situation, where key decisions have been made without Ukraine being at the table without even Europe involved. The âUkraine effectâ has already revealed shifting global dynamicsâwhile the U.S. supplies weapons, it still depends on Chinese suppliers, just as Russia does. This means China is, in effect, fueling both sides, much like the U.S. once did when it was in a dominant position. These peripheral factors will inevitably shape future negotiations, yet instead, we are expected to be captivated by the idea that Witkoff once carried a gun to collect rent in the Bronx from what appears to be poor neighborhoods. This isnât a movie script.
Ultimately, the Israeli-Palestinian issue will not be resolved through economic initiatives but through decisions about land, people, and sovereignty. If this article had true journalistic integrity, it would focus on not only what Witkoff actually believes, rather than what he wants the public to believe but even more importantly his discussions with the adversary not with allies.
I donât know about you, but Iâd rather have a proven street smart entrepreneur negotiating these geopolitical deals vs. an overly credentialed neophyte with zero real world experience. Look where that got us over the last 30 years.
Getting important stuff done is more important than endless dithering and hand wringing. Sure, some deals may not be 100% perfect, but a lot of progress will be made in the end.
Great. I hope you feel the same way when China buys the UK. Itâs just real estate. Relax.
Moron.
My impression of NY real estate is that you are dealing in a world were there are lots of powers that the average man in the street is only dimly aware of. These powers are not afraid of using muscle if they see their interests threatened. They are not afraid of all out war if it comes down to it, but realize that war is very tacky and rarely results in the desired results.
My impression of world power relations is that you are dealing in a world were there are lots of powers that the average man in the street is only dimly aware of. These powers are not afraid of using muscle if they see their interests threatened. They are not afraid of all out war if it comes down to it, but realize that war is very tacky and rarely results in the desired results.
I think we have the right man for the job.
Come on everybody this is nonsense, the Arabs are NEVER going to give up on this! Why should they?
After all some 900 years ago the âCrusadersâ fought their way into the place (uninvited) but were ultimately ejected some 200 years later.
Come 1917 the Balfour Declaration makes the simply preposterous claim that is a Jewish homelandâ, and then come 1945 the Arabs are told there has been an atrocity in Germany and guess who is going âpay the billâ: THEY ARE!
One day, not tomorrow or even the next day, but someday the Arabs will get the Bomb and then it will be âgame overâ as they say today.
Trump does think outside the box. He favours a one state solution where, by implication, everyone has equal rights. That approach allows Trump to avoid advocating the pointless two state solution while ensuring that a permanent peace in the Middle East will be a post apartheid Israel that gets round the disastrous decision by the United Nations to create the State of Israel in 1948.