Front Burner - Real estate, crypto, Middle East deals: Who is Steve Witkoff?

Episode Date: June 4, 2025

A little over five months ago, few outside of the New York City real estate scene knew who Steve Witkoff was. Now, as the U.S. special envoy to the Middle East, he’s not only been tasked with trying to end the war in Gaza but he’s also at the centre of negotiations with Russia over the war in Ukraine and with Iran to secure a new nuclear deal. To understand how one of President Donald Trump’s closest friends came to spearhead negotiations in some of the most complex foreign policy files of the last few years we talk to Isaac Stanley-Becker, staff writer at The Atlantic who recently wrote a profile on Steve Witkoff. Fill out our listener survey here. We appreciate your input!For transcripts of Front Burner, please visit: https://www.cbc.ca/radio/frontburner/transcripts

At Desjardins Insurance, we put the care in taking care of business. Your business to be exact. Our agents take the time to understand your company so you get the right coverage at the right price. Whether you rent out your building, represent a condo corporation, or own a cleaning company, we make insurance easy to understand so you can focus on the big stuff, like your small business. Get insurance that's really big on care.

Find an agent today at Desjardins.com slash business coverage. This is a CBC podcast. Hey everybody, I'm Jamie Poisson. At the start of his second term, Donald Trump promised to end two wars, the war in Ukraine and the war in Gaza. The man that he has trusted to spearhead these deals isn't Secretary of State Marco Rubio. Instead, it is Trump's very close friend of nearly 40 years, Steve Witkoff, the US special envoy to the Middle East.

Now, Witkoff, a lifelong real estate developer, finds himself at the center of some of the highest stakes negotiations on the planet. He's got his work cut out for him. Despite securing a ceasefire in Gaza earlier this year, negotiations for a new one have reached an impasse. And despite cozier relations with the Kremlin, the war in Ukraine saw recent significant escalations on both sides. On top of that, Trump is now seeking a new nuclear deal with Iran, and Witkov is playing a key role in that too.

Isaac Stanley Becker spent some time with the special envoy and those around him for the Atlantic, and today we're going to talk to him about how Steve Witkoff became the shadow secretary of state, what makes him tick and whether being a shrewd businessman and Trump's best friend is really enough to achieve peace. Isaac, thank you so much for being here. Oh, thank you for having me. It's such a pleasure. As you pointed out in your piece, which is great, by the way, not many people outside

of the New York City real estate scene knew who Steve Witkoff was five months ago. And can you just take me through who he is and what he was doing before he became essentially the shadow secretary of state? Sure. He was a business guy and in many ways he still is a business guy. He's a New Yorker. He was born in the Bronx, raised on Long Island. He went to law school and was working as an associate at a law firm in New York, which is when he first met Donald Trump in the 1980s. Donald Trump was a real estate developer and the firm that Witkoff was working at represented Mr. Trump in some of his real estate dealings.

They met in that context. Trump made a big impression on him and he actually credits Trump with leaving behind his legal career and going into real estate investing, pursuing a similar path as the president. And they remained in touch and became golfing partners and especially in recent years as the president and then former president and then again candidate and then again president encountered some difficulties after the attack on the Capitol on January 6th, when many of Trump's allies deserted him.

Witkoff really stuck with him and remained extremely loyal and that really deepened their bond and some of the people I spoke to, including the White House chief of Staff, said that Steve Witkoff is not just Donald Trump's friend, he is his best friend. And he has given his best friend quite a lot of responsibility. And just tell me how that came to be that Donald Trump's best friend, someone who actually does not have a background in diplomacy or international relations end up becoming a special envoy entrusted with the most important geopolitical negotiations of our time. Well, it's a really interesting story and I think a story that offers a lot of actually insight into the way that Trump operates. I should say that in some ways the role reprises

some of the responsibilities that Jared Kushner, the president's son-in-law, had in the first term. He was point person on important issues in the Middle East and some other sensitive international negotiations, including trade issues. So there is a kind of history of Trump entrusting family members or close friends, really people in his inner circle with some of the most sensitive international issues and Witkoff is now playing this role. I spoke to Senator Lindsey Graham,

Republican of South Carolina, a close Trump ally about this. And he was taking me back to the Republican primary in, you know, 2023, 2024. Trump is gaining steam in that contest. It looks like he's going to be the candidate. And as that's unfolding, what Senator Graham told me is that there are discussions with Witkoff over golf. And Senator Graham and Witkoff and then candidate Trump were talking about how Witkoff might like to occupy himself during a second Trump term. Senator Graham said, but you want to run for Senate. He says, no, I want to do something more informal. What I'd really like to do is to help in the Middle East. And Senator Graham tells him

about the special envoys, which is a somewhat informal role. This again is in Senator Graham's telling. And Witkoff says, yeah, that's what I'd like to do. And that's how he gets initially tasked with this role specifically in the Middle East. Now, there's an important breakthrough actually before Trump takes office in January, before the inauguration. Witkoff plays a rather important role in helping the Biden team secure that ceasefire and hostage deal that sees the release of a number of hostages in January. And so he has this early success. Peter Van Doren Tucker, when I first got in, and I was talking to Brett McGurk, who was the envoy on behalf of Biden, he was a smart guy. Yes. He just didn't have a great boss giving him direction.

So he couldn't really speak on behalf of Biden. I was able to speak on behalf of Trump because we talked about it. We had a great conversation about it. He said to me, this is where I want to get to, Steve. And so when I went in there, I went in with the imprimatur of the president and became a, you know, that's the difference maker. Then when another opportunity arose for a prisoner swap, this time with Russia, with an American school teacher who'd been imprisoned in Russia, the president sends Witkoff because the thinking was that he had succeeded in one realm, so why not try his hand in Russia? Do them all. Yeah. Exactly. And so that's how Russia becomes

part of his portfolio, the Russia-Ukraine conflict. And then by this time, it was just a matter of trust and his credibility with the president. And so when there was an effort to strike a new nuclear deal with Iran, it was Steve Wittkopf who has made point with that. So he is really Trump's point person for the most sensitive international issues, not just in the Middle East, but across the board. When I say I speak for the president, it's not because I presume what he's thinking. It's because I ask what he's thinking.

He is the president. I'm in my job only because of him. And to me, I give him the respect of always asking the question, where do you want to get to, Mr. President? ["The President's Theme"] Can you tell me a bit more about what he's like? You know, how you found him before we started this interview, you remarked to me briefly that he was just one of the most interesting people you had ever had the chance to write about and also different from a lot of other people in the White House? Just how?

I think he's extremely energetic and curious and almost kind of wide-eyed about his responsibility. I asked him what the most surprising thing was to him about the work that he's engaged in. And he said at first, the press, he's gotten beaten up, you know, in the press, including the New York Post, the Murdoch-owned tabloid. But he said the second thing was how much he loves it. I think he's really enjoying his high flying role on the world stage. And some of this comes from a place of deep personal grief. He lost a son. One of his sons died of a drug overdose when he was in his early 20s. And it was, as I'm sure your listeners can understand, it's just the most devastating thing to happen to a parent. And he really does see some of the work he's doing as an effort to honor his son's memory to do good and to kind of live out certain principles based on that just terrible personal grief.

I mean, it used to be that I couldn't use the word blessing because of my boy of his death. But now I can say I was blessed, but for this overwhelming tragedy. And I think my son Tucker allows me to be, to have this sense of, I relate to a lot of the hostage families You know many of these families are never going to get their children back. I think that this sense of

Sensitivity or empathy that I have I can relate to them I they will so he isn't someone who has you know cut his teeth in government and is looking to ascend and is playing the game of government he for all of his inexperience or different kind of experience, is approaching this in a really outside the box and kind of personal way. LESLIE KENDRICK You mentioned earlier that early win that he had, the ceasefire that he helped secure between Israel and Hamas. It was essentially the same deal the Biden administration had proposed months prior,

that Israel had continuously rejected. And just, can you tell me more about how Witkoff played a role in getting that through? Well, I think the dynamics between the Trump administration and Trump personally and Netanyahu's government and the kind of assessments that the Israeli prime minister and the people around him are making about the relative merits and benefits of having Trump in office versus Biden or Republican versus Democrat are fascinating and will be studied by diplomats and historians and scholars of international relations for years, because my sense is that there was a desire to essentially buy some goodwill with the incoming Trump

administration by acceding to this deal that not only the Biden team wanted, but Trump's incoming team made clear that the Biden team wanted, but Trump's incoming team made clear that the incoming president wanted. And, you know, Witkoff was quite stern with the Israelis. As I understand it from my reporting, he said to the head of the Mossad, David Barnea, you know, if you don't agree to this deal, you're going to need to go home to your friends and explain to them why their own children are still being held in captivity and haven't been released. And this is something that's stunned kind of longtime diplomats who've studied the US-Israel relationship,

just the way in which Trump and his team have been willing to be tough with the Israelis and at times as necessary, you know, sideline them entirely from the process when they see fit, when they wanted to get Aidan Alexander out of captivity. They didn't even involve the Israelis in that process. They worked through an intermediary with Hamas to get that done. The parents of the last living American hostage now released, Edan Alexander, spoke with the press at the hospital their son is now recovering in. First and foremost, I want to thank President Trump, Ambassador Witkoff and the special

envoy, Bola. During our family reunion, Ambassador Witkoff was waking up America's officials at 3 a.m. on the East Coast just to share the good news and encourage them to speak with our family. It's remarkable that that kind of approach is being taken by a Republican administration and by Donald Trump's administration, who puts himself forward as a champion of Israel and Israeli interests. And I think the way that Wyckoff sees it is that he has the backing of Israeli society

and the Israeli public, and that that's as important, if not more important, than the support of the Israeli government. At Desjardins Insurance, we put the care in taking care of business. Your business to be exact. Our agents take the time to understand your company so you get the right coverage at the right price. Whether you rent out your building, represent a condo corporation, or own a cleaning company, we make insurance easy to understand, so you can focus on the big stuff,

like your small business. Get insurance that's really big on care. Find an agent today at Desjardins.com slash business coverage. We're all looking for great places to visit in Canada. One of my favorites is the Stratford Festival. The theater is truly of the highest caliber, and there's so much selection.

They have 11 large-scale shows on stage and trust me, whatever is on manure there will be exceptional. People always think Shakespeare when they think of Stratford, but it's so much more. Broadway musicals, family shows, classic comedy and drama. Whether it's Robert LaPage's Macbeth or Donna Fiora's Annie, you will be blown away. It's the perfect Canadian getaway. To quote William Shatner, who got his start in Stratford, every Canadian should make the pilgrimage to Stratford. Start your next adventure at StratfordFestival.ca. Of course, a new 60-day ceasefire deal in Gaza was proposed last week. I think that we are on the precipice of sending out a new term sheet. And I have some very good feelings about getting

to a long-term resolution, temporary ceasefire, and a long-term resolution, a peaceful resolution of that conflict. LESLIE KENDRICK, HOMOS, CREDITS, AND DEPARTMENT OF CREDITS Hamas has agreed to the outline but proposed some amendments, including a permanent ceasefire and full withdrawal of Israeli troops, a permanent end to the war. And Witkoff has now called their response unacceptable. And he has said that Hamas should accept the proposal as is.

And so, like, despite his success earlier this year, is there a sense that he is reaching the end of his ability to bargain, maybe with both parties. How are people evaluating him today? BOWEN I think the difficulties of these negotiations has been made utterly clear. And in some ways, the current impasse has echoes of an earlier failure in March to extend the initial ceasefire struck in January. And I spoke for the peace to someone who works with the leadership of an Arab Gulf country who said that just the complexity and the nuance of the Gaza issue this person thought had humbled

Witkoff. And I think that there's truth to that, that there is a breakthrough, there's some success, but this is a really, really vex negotiation and dealing with these parties and finding a way to not just bring them to the table, but get them to agree has been extraordinarily difficult. And we're not just seeing that between Israel and Hamas, but also between Russia and Ukraine, the intensification of that conflict, even as there has been some progress in bringing the two sides to the table just in recent days to talk each day just brings new evidence of the challenges of what he's trying to accomplish and we haven't even gotten to the Iran issue.

Park Iran for a minute, I want to come back to it, but just on the Russia-Ukraine stuff, I know that he's met with Putin on his own. How are you Mr. President? Great, just great to be here today. Without his own interpreter, relying only on the Kremlin one, which is, I think, quite unusual. He also gave that interview, Witkoff gave that interview with Tucker Carlson, where he was essentially criticized for parroting Russian talking points on the war in Ukraine. They're Russian speaking. Yep.

There have been referendums where the overwhelming majority of the people have indicated that they want to be under Russian rule. I think that's the key issue in the conflict. So that's the first thing. When that gets settled, and we're having very, very positive conversations around that. And Russia controls that. In fact, some of those territories

are now, from the Russian perspective, part of Russia. Correct. That's correct. But this has always been the issue. Well, like, just tell me more about the reaction to how he's been dealing with Russia in particular. I think this is really where Wyckoff has gotten and has received the most severe criticism is in his dealings with the Kremlin and the kind of approach he's taken or read out he's given of those conversations once back in Washington. He has met with Putin a number of times and he's done so without career diplomats, as you said, without an interpreter, without a translator. And what I learned in the course of my reporting was that the reason for that is that those

were the terms set by Putin for their meeting, for their conversation, and those were terms that he was willing to accept. And that really stunned longtime Russia watchers who just said, Putin and the people around him, they are very skilled at this and they are expert manipulators. And I think adding to their concern was the fact that Witkoff then came back to Washington and he did seem to echo these Kremlin talking points. And in seeming to take Putin's kind of efforts at charm, at face value and interest in friendship with the American president. And I put this to some of the people around Wyckoff and they said, this is his effort at emulating

Trump's approach to diplomacy, which is based heavily on personal relationships and on charm and on returning charm showed to him by foreign leaders. But I think it remains a kind of open question whether Witkoff has a clear-eyed understanding of Putin and what he's really after and whether it is true as Witkoff sees it that this is all just kind of negotiations and you have to get the two sides to a kind of 50-50 deal where they each feel like there's fairness and how things are being apportioned or whether this is someone with a deeply held ideology that sees Ukraine as properly Russian and he will stop at nothing to make that happen. Whether he believed that initially, whether he's come to see that, we've seen Trump voice some more criticism and complaints with Putin and so whether that actually changes the approach,

whether we see more sanctions. I think we're at a sensitive point in these negotiations and where Washington takes things will be, you know, really important to watch. I was struck by when you spoke to Wyckoff, he seemed actually most confident that he would be able to reach a nuclear deal with Iran. This week, the US sent their proposal for that deal to Iran. And so far, I mean, I've seen multiple reports that suggest that Iran is just going to turn it down.

And so where was his optimism with that deal coming from? I was struck by that as well. And what his view was is that Iran was really at a crisis point. And his assessment was that they were in such a dire situation that they would be prepared to not just strike a deal, but strike a deal that would be favorable to Washington. And there's a lot of reasons for that, some of which we can assess based on what's known publicly, the way that various Iranian proxies have been defanged. And no doubt there's also sensitive intelligence that he's reviewing. But we have to say based on some of the conflicting statements just in recent days and weeks from the

administration that the state of this remains very muddied. And so as you said, there was a proposal put to Iran, and that proposal allowed for some very limited enrichment in some ways similar to the 2015 deal struck by the Obama administration. But then we saw President Trump come out and say that Washington would not accept any enrichment. So whether they're playing some kind of three-dimensional chess or four-dimensional chess, and this is all part of some grand strategy, who knows?

But it's hard to see exactly how this is all amounting to an agreement that is far superior to that 2015 deal, if Iran is even willing to agree to something resembling that arrangement. But I do want to also discuss some potential conflicts of interest here. So Trump and Witkoff recently went on a tour of the Gulf states, meeting with Arab leaders. Trump of course accepted the gift of that Boeing 47-8 jet from Qatar, and that drew some criticism from pro-Israel media like the outlet Jewish News Syndicate, accusing them of being bought by an ally of Iran. And just, yeah, how did Witkoff respond to that?

Well, in some ways these are two different, two distinct issues, even though, of course, they're related. There have been questions that have dogged Witkoff about some of his past business dealings that have involved Qatar. A sovereign wealth fund based in Doha helped rescue him from a real estate deal that went south in recent years. And so this has prompted criticism that he's in the pocket of Qatar. And he really bristled at that suggestion when I discussed this with him and said, he was talking about his own Jewish faith and his ties

to Israel. And he said, I'm a Krav Maga double black belt. This is a kind of martial art that's used in Israeli military training. And, you know, I'm no Qatari sympathizer. He said, you know, what I am is a truth teller. But then there's the more ongoing question of the president's, you talked about his transactional foreign policy, there's also just straight up,

business transactions and personal transactions that are being done that coincide with some of these diplomatic and foreign policy dealings. You mentioned the airplane being donated by Qatar. And then in, in Wittkopf's case, you know, he was a, one of the founders of this cryptocurrency company that is now managed and run in large part by the Trump family, along with one of Witkoff's sons. It's called World Liberty Financial, mostly owned by a Trump family entity. So Witkoff himself told me that even though he's a co-founder, he now has nothing to do with this. He's in the process of divesting himself from some of his business work,

meeting with the kind of government ethics professionals to get the necessary paperwork done. This of course does not apply to his adult son who is not a government employee and is doing lots of globe trotting, snapping up deals and working with people, foreign and domestic to gain investments and advance this cryptocurrency business. You talked about how Witkoff and his strategies have kind of upended diplomacy and diplomatic circles.

I imagine perhaps at the top of that list is Marco Rubio, the actual Secretary of State. Do we have a sense of how he feels about Witkoff's role as kind of this chief negotiator in the world? You know, I don't know what's in Marco Rubio's heart. What I do know is that when I was working on this piece, it became very clear to me how much Witkoff's profile and image, how important it was to the administration and to the White House because I received unsolicited comments from both Vice President J.D. Vance and Marco Rubio praising Witkoff. And I put this question just in my own interviews

and reporting to a number of people about that relationship, about how Rubio views all of this. And they maintain to me that Rubio had a lot on his plate, for what it's worth, he's been point on the very important events unfolding in Syria and the administration strategy and approach there. He's now also the interim national security advisor. So he's got a lot on his plate. It is no doubt true that significant duties that would ordinarily fall to the Secretary of state have been taken away from him

and are being assumed by, you know, Whitcoff. It's like if you're a host of a podcast, but all the most important conversations are being handled by someone else. But I think that there's other kind of interesting factors here and one is that Marco Rubio has had to put in the work to gain favor with Trump's base, with Trump's team, with the kind of MAGA universe. And I think that most people think that Marco Rubio has future political ambitions, be that

president or vice president. And so it serves him well to be a team player and to do what he's asked to do, to not complain, to let the president assign whatever he sees fit to his friend, and to stay on sides. And so I think that there's a kind of a long-term calculation by Rubio here that what's most important to him is not that he's the guy doing X or Y negotiation, but that he's the guy who doesn't step on the wrong person's toes and, you know, get exiled. Isaac, this was great. It was so interesting.

Thank you so much for coming by. Oh, thank you so much for having me. All right. That is all for today. I'm Jamie Poisson. Thanks so much for listening. Talk to you tomorrow.