On the menu today: This is the last Jim-written Morning Jolt until June 28. Yesterday, the White House issued two related statements that were intertwined, yet seemingly incongruent. President Trump announced that he will make his decision regarding the potential use of military force within two weeks. Theoretically, he could make that decision any day within that window, but Trump said he was holding off because of “negotiations that may or may not take place with Iran in the near future.” But just moments later, White House Press Secretary Karoline Leavitt said Iran could have a working nuclear weapon “within a couple of weeks,” with some U.S. officials putting the timetable at 15 days. The future of the Middle East now depends upon the expected talks between U.S. special envoy Steve Witkoff and the Iranian government.
Trump’s Two-Week Reprieve
Two statements from White House Press Secretary Karoline Leavitt in the same briefing Thursday:
Now, regarding the ongoing situation in Iran, I know there has been a lot of speculation amongst all of you in the media regarding the president’s decision-making and whether or not the United States will be directly involved. In light of that news, I have a message directly from the president, and I quote. “Based on the fact that there’s a substantial chance of negotiations that may or may not take place with Iran in the near future, I will make my decision whether or not to go within the next two weeks.” That’s a quote directly from the president for all of you today. [Emphasis added.]
And then later in the same briefing:
Iran has all that it needs to achieve a nuclear weapon. All they need is a decision from the Supreme Leader to do that. And it would take a couple of weeks to complete the production of that weapon, which would of course pose an existential threat, not just to Israel, but to the United States, and to the entire world. [Emphasis added.]
The New York Times puts a more precise number on that “couple of weeks”:
Some American officials said those new assessments echoed material provided by Mossad, Israel’s intelligence agency, which believes that Iran can achieve a nuclear weapon in 15 days. [Emphasis added.]
So, we’re giving presidential special envoy Steve Witkoff two weeks, traditionally defined as 14 days, to reach a deal, while portions of our intelligence community believe that Iran can build a working nuclear weapon in 15 days.
Isn’t that cutting it a little close?
That’s barely more than one Scaramucci. The whole Middle East could look completely different one Friedman Unit from now.
The future of the Middle East and the fate of Israel now rest on the shoulders of Witkoff.
For those not familiar with him, his role as the lead U.S. negotiator in dealings with Hamas and Israel, Russia and Ukraine, and now Iran are his first three major experiences in international diplomacy. His first role in government was as one of nearly 200 business executives named to President Trump’s Great American Economic Revival Industry Group in April 2020, during the pandemic. The industry group met through conference calls.
With that said, Witkoff has known Donald Trump for a long time. Witkoff was called as a witness during Trump’s fraud trial in the New York attorney general’s $250 million civil case against the Trump family and its namesake business, and at that trial, he described how they met:
On the stand Witkoff recalled the origins of his budding friendship with Trump, which apparently started at a New York City deli in 1986 after the pair had worked on a transaction together.
“I ordered him a ham and swiss,” Witkoff said, remembering that Trump had no cash on him at the time.
Seven or eight years later he ran into Trump, who remembered “the sandwich incident,” Witkoff testified. The two became friends after that; Witkoff even advised Trump on tax breaks during his presidency.
From a New York Observer profile in 1999:
Born in the Bronx, Mr. Witkoff grew up in Baldwin Harbor, L.I., and got his law degree from Hofstra University. After graduating, he landed a job at the real estate firm Dreyer & Traub, where one of his clients was Donald Trump.
The young lawyer, however, was more interested in emulating the famed developer than doing his legal paperwork. So in 1985, he and his fellow attorney, Larry Gluck, started touring Washington Heights in a beat-up 1978 Buick, searching for cheap buys. He wound up digging trenches and doing his own plumbing work when his rental income slumped. But he learned a thing or two about how to turn distressed properties into money makers.
Witkoff’s career in managing real estate assets, from apartments to office space, boomed. Through this, you could say he developed a form of experience in international relations:
Qatar’s sovereign wealth fund bought the Park Lane Hotel overlooking Central Park — once called the “world’s greatest site for development” — as the Middle Eastern nation continues its push into New York real estate.
The Qatar Investment Authority paid nearly $623 million to acquire the 46-story hotel at 36 Central Park South from Steve Witkoff’s company, property records show. PincusCo first reported the sale.
It was not immediately clear what the $450 billion sovereign wealth fund plans for the property, which Harry Helmsley developed in the 1960s.
Witkoff bought the hotel in 2013 for $654 million with a plan to convert the bulk of the building’s 600 or so rooms into high-end condos. But by 2016 he and his partners — Harry Macklowe, Howard Lorber’s New Valley and Highgate Holdings — had decided the Billionaires’ Row market had become oversaturated. They put the conversion on hold.
A few months later, Chinese developer Greenland Group bought a 41 percent stake in the project from Kuwait Strategic Investors. . . .
Witkoff and his partners had high expectations, and no one met their $1 billion asking price. The owners refinanced the hotel in 2019 with a $615 million loan from Deutsche Bank and JPMorgan, and the Abu Dhabi fund increased its stake in the property as part of the DOJ’s effort to recover funds.
Also, this year, as Witkoff handles sensitive Middle East negotiations, his son Zach is simultaneously negotiating a $2 billion cryptocurrency deal with a company controlled by the United Arab Emirates’s ruling family.
At a presidential event in Las Vegas in 2018, Trump spoke about Witkoff with genuine affection:
I want to thank a friend of mine, Steve Witkoff. You know, people don’t realize Steve started out as a lawyer — a very good lawyer, a top lawyer in New York. And then he said, “I’m going to go in the real estate business because I can do this, too.” He saw me do it. (Laughter.) And he said, “If Trump can do it, I guess I can do it, right?” (Laughter.)
Steve was a great — actually, he was a great real estate lawyer. And he represented a lot of us from the Manhattan real estate world. And one day, he said, “Hey, maybe I’ll do this.” And he bought a little building, and it worked out. Then he did another one, and it worked out. And now he has a lot of them, and he’s become a very wealthy, successful man. And he’s my pal. And it’s nice that you’re here, Steve. Thank you very much. (Applause.) Special guy.
Of course, being the president’s longtime friend, his former lawyer, and having made a fortune in Manhattan real estate are an unorthodox résumé for a man handling the most sensitive and high-stakes international negotiations on behalf of the United States.
From the Wall Street Journal, in 2024:
The appointment of another developer — as opposed to a diplomat — deepens the sense that Trump ultimately views the Middle East crisis as a complicated property negotiation. Witkoff shares that view, seeing it in part as “one giant real estate deal,” according to a person familiar with his thinking. And choosing someone so close to the family, say insiders, means Witkoff should be able to have some continuity with [Jared] Kushner’s approach.
The thing is, the Iranian nuclear program, Russia’s invasion of Ukraine, Hamas’s determination to kill Israelis whenever and wherever they can — these aren’t just real-estate deals or redrawing lines on a map.
If you screw up a Manhattan real-estate deal, millions of dollars could be lost, but the fallout is only metaphorical. If you screw up negotiations over a nearly complete Iranian nuclear bomb, countless lives could be lost, and the fallout would be literal.
I often refer to him as Steve “Hamas Duped Me” Witkoff. Some might think that’s unfair, but that’s Witkoff’s own words in describing his early negotiation efforts in March:
“I was in Doha. I met with many of the Arab leaders at the Arab Summit. 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 . . . but I thought we were there and evidently, we weren’t. So, this is on Hamas. The United States stands with the State of Israel.”
I don’t understand how a guy can be appropriately wary when negotiating a lease for office space, but so credulous and trusting when sitting across the negotiating table from Hamas.
Then there’s the matter of Witkoff periodically going into these negotiations alone, not even taking along a U.S. State Department translator:
Steve Witkoff, who has been tasked with negotiating an end to the war in Ukraine, met with Putin in Moscow for several hours on Feb. 11, on March 13, and in St. Petersburg on April 11, and “used their translators,” one of the Western officials said. “If they speak to each other in Russian, he doesn’t know what they are saying,” the official added, referring to Putin and the interpreters.
Witkoff, a former real estate mogul and cryptocurrency trader, does not speak Russian. By using Kremlin interpreters, he ran the risk that some of the nuance in Putin’s messages was missed and he would not have been able to independently verify what was being said to him, two former American ambassadors said.
Reportedly, the translator Witkoff used for his meeting was Natalia Koshkina, second secretary of the Russian MFA’s linguistics department. She is also apparently the chief interpreter for Sergey Naryshkin, who is the head of the Russian Foreign Intelligence Service, the successor agency to the First Directorate of the KGB. If she’s got the kind of clearance needed to serve as the translator for the chief of the Russian spy agency, then there is an excellent chance that she herself is a member of the Russian FIS.
Now, the U.S. government has rooms full of people who not only speak Russian, but who have spent a significant chunk of their adult lives studying the Russian government. These people would probably not only be able to translate Putin’s words fluently, they probably would have some degree of insight into Putin’s word choice, tone, body language, contradictions from past statements, etc. For whatever reason, either Witkoff didn’t think he needed any of them, or it never crossed his mind to bring his own translator.
The thing is, no matter how underqualified, underprepared, and gullible Witkoff may seem, and no matter how shady his family’s business ties seem, I have to root for him to succeed in convincing Iran that it must give up its nuclear weapons program. The consequences of failure are just too dire.
Still, if the negotiations do not succeed, it will be more than fair to wonder if Witkoff was the right man for the job.
ADDENDA: If you haven’t read it already, check out Andy McCarthy’s analysis of why the U.S. intelligence community’s assessment of the Iranian nuclear program got vaguer in the summer of 2024:
I believe the ODNI dragged its feet about producing a statutorily required report and then provided incomplete disclosure because timely and comprehensive disclosure would have hurt the Democrats’ chances in the 2024 election. That is, it would have given Trump a club with which to hammer Biden and Harris, whose administration said it would prevent Iran from getting nuclear weapons but was unwilling to do anything about it — indeed, the Biden-Harris administration was laboring to revive Obama’s Iran nuclear deal, which put Tehran on a glide path to becoming a nuclear weapons power.
Over in Commentary, Tevi Troy, who catches every reference to Die Hard on the Three Martini Lunch podcast, examines the three big Biden administration tell-all books. He observes of the Biden inner circle, “If you’re supporting a Democratic incumbent and you think the New York Times is conspiring against you, you have crossed the line into madness.”