Michael Wolff’s Messy Attempt to Explain Why He Was Helping Epstein

Let's start this episode with a line that should make anyone in communication sit up a little straighter.

You send an email to him saying, I hear CNN is planning to ask Trump tonight about his relationship with you, either on air or in scrum. Afterwards, he writes back, if we were able to craft an answer for him, what do you think it would be? And then you say, I think you should let him hang himself.

A journalist wrote that to Jeffrey Epstein. Not about exposing him, not about confronting him, but about how Epstein should handle Donald Trump. That journalist was Michael Wolff, a best selling Trump biographer who built his career on access. And now the emails he sent Epstein have become their own crisis case study. In this episode of the podcast, we are looking at the messaging behind those emails, not the salacious details, not the conspiracy theories. There are plenty of other places for that and I feel like I've listened or watched to all of them. But if you know me, if you listen to this podcast, you know I'm always interested in the messaging and also the patterns. Let's talk about the communication patterns buried Inside more than 20,000 Epstein related documents released last week by the House Oversight Committee files that show how Epstein operated his influence network from 2009 to the months before his 2019 arrest. Because Wolf's explanation for why he sent those emails is one of the most revealing crisis management performances I've seen in a long time. It tells you as much about him as it does the emails. This week the episode is going to focus on a long on air conversation between Michael Wolf and Joanna Coles on the Daily Beast podc. They released an emergency podcast because Michael Wolf was all over those emails. Joanna Coles pressed Wolf on all the emails with Jeffrey Epstein. Joanna Coles, to her credit, really pressed Wolf on these emails. And Wolf, we hear, tried to explain, defend and reframe the choices he made as a reporter who ingratiated himself with a source. The clips you'll hear come directly from that interview. I have a link to this interview in the show Notes. I listened to this interview last week along with so many other podcasts and content creators and media outlets and reporters breaking down what they saw in a lot of these emails. I kept going back to Wolf because he's a journalist and because he did this interview, I had to focus squarely on him. Even though there are a lot of other people who are wrapped up in this whole Epstein scandal. I want to focus on Wolf because he's the one who came out and did this interview with Joanna Coles, which I have to give him credit for because everybody else out there is quiet. Mum's the word. But this I found interesting. The emails that came out associated with Michael Wolf show him, yes, partly as a curious reporter, but also as a tactician, someone fluent in narrative engineering, someone willing to help Epstein shape a response to protect his own interests. At one point, Wolf warns Epstein that CNN is preparing to question Trump about their relationship.

You send an email to him saying, I hear CNN is planning to ask Trump tonight about his relationship with you, either on air or. Or in scrum.

Afterwards, Epstein immediately asks how Trump should respond.

He writes back, if we were able to craft an answer for him, what do you think it would be?

And Wolf answers, like someone managing a client, not interviewing a source.

And then you say, I think you should let him hang himself.

He even frames a potential benefit if Trump lies.

If he says he hasn't been on the plane or to the house, then that gives you a valuable PR and political currency.

He outlines how Epstein could weaponize Trump's answer.

You can hang him in a way that potentially generates a positive benefit for you.

And he describes how Epstein could save Trump to create leverage, or if it.

Really looks like he could win, you could save him generating a debt that's not reporting.

That's message strategy. And it puts Wolf squarely inside the machine he claims to document. When Wolf was confronted about this in the interview, he did what many people under scrutiny often do. I see it in the press, I see it in responses. I see it in my own job. He minimized. He called the emails embarrassing. He suggested anyone would rewrite an email once it became public.

You know what emails sound like? Would one have rewrite, rewritten them in hindsight? Yeah, of course. You know, emails always are. Oh, that's. That's. That's embarrassing.

Then he reframed the entire situation. He said he was in a position no one else was in, which is absolutely true.

I am in this. I am where no one else is. I am in proximity to a story, which actually most people don't see at this point.

He cast himself as the lone true teller, the only one who, quote, saw the elemental story.

I'm the person who sees this, this elemental story.

This is classic crisis framing. Whether Wolf was trying to do that or not, it was instinctual with him, apparently. But if your behavior looks questionable, you're elevating the mission. Make it sound noble, make it sound necessary, make yourself sound like the insider who had to break the rules to expose the truth. But that's not accountability, that's self Justification. Now, let's look at what Wolf really admitted, because he was insisting he was not Epstein's media advisor in these emails.

What strikes me is that you're frequently giving advice to Jeffrey Epstein about how to handle the media, how to use the media. Were you his media advisor?

No. He had.

I mean, but everything he describes next contradicts that. He explains that his media knowledge gave him credibility with Epstein.

Part of my entree here, that I knew about the media, that gave me the kind of cachet that got me a place at the table which has gotten me the Epstein story.

He admits he was acting and playing a role.

Am I acting? Am I play acting?

Right. Are you protecting?

Am I playing a role? And the answer is yes.

Even brags about using charm tactically.

I think, as my mother would say, you get more with a little honey.

And then he reveals the core belief driving all this.

This is a story that I have told as often as I can, in as many places that I can. The story of Donald Trump's relationship with this pedophi. A story that virtually and certainly many of the journalists that I'm sure are now criticizing me have chosen not to pick up.

And here's the ethical tension. If the ends matter more, then the means start turning into excuses. And that's where Wolf lives in this story. He wants credit for telling the truth about Epstein and Trump, but he does not want accountability for how he got there. This is a point where I should add Michael Wolf. Even if you haven't heard of him, you probably have heard of him. He's written a number of books about President Trump. In 2018, he wrote Fire and Fury, Inside the Trump White House, 2019 siege Trump under fire, 2021 landslide, the final Days of the Trump presidency, and in 2025, all or nothing, How Trump Recaptured America. Each book offers a narrative based on interviews, inside access, and sometimes anonymous sources, which has led to the discussion about the reliability and ethics of Wolf's reporting, especially as it relates with his connection to these Epstein emails. It makes you wonder how much of the information in these books really came from Epstein, since he considered him such a key source. Since Epstein had an ax to grind against Donald Trump, it's clear that's where he's getting a lot of his access. I can understand the gray area here. Now, Michael Wolf lately has been very prolific on social media. I follow him on Instagram. His posts often reveal very inside information. It's a fascinating post to follow. I'll also include the link in the show notes. It's as good for the inside information as it is to see Michael Wolf's home. I believe he lives in Long island, but his home is absolutely beautiful and he always does these posts from different rooms. I have to be honest, many times I'm just looking at his home rather than listening to what he has to say. But here are the ethical red flags. I loved following Michael Wolf. Now when I look at his posts, I'm always going to look at him a little bit differently. Wolf responds to criticism the same way many people do in a reputational crisis. He changes the frame, says, I'm not a pedophile, I'm a writer.

I am not a pedophile, I am a writer.

He says he never saw girls or a massage room.

You're just hearing things. So, I mean, that was, I mean, my relationship with, with, with Jeffrey Epstein did not go. I mean, actually I have never, in all of the hours that I have spent with him, I have never, never saw, saw any interaction with women.

He says he stayed because he had 100 hours of Epstein talking.

There are hours and hours, upwards of 100 hours of Jeffrey Epstein talking about many things.

But the absence of witnessing crimes does not absolve the presence of complicity. And his own words reveal how far he was willing to go to maintain proximity. Because once you believe the story is worth any cost, your ethics start bending without you noticing. And here's where the research comes in. According to Pew Research, only 26% of Americans say they trust the information media outlets report. That was from a study in 2023. And this is why trust in journalism is scraping the floor. When reporters defend troubling behavior as just how access works, the public hears something very different. Jake Tapper learned this when he published the book Original Sin about President Joe Biden choosing to go ahead with the nomination as opposed to stepping down. Jake Tapper received a lot of blowback from other people in the press, from the public, from social media. Heck, even I experienced it when I did content just around that book, which, by the way, I found that book fascinating. But a lot of people accused him of withholding information to save it for a book. And I said at the time, and I'll include a link in the show notes to my podcast about the Original Sin book and the Jake Tapper issue. It's that journalists nowadays, to remain relevant on air and to remain employed, they need to create caricatures for themselves. They need to have a strong social media background and also content like books to back it up. Michael Wolf really is no different than Jake Tapper here. However, Jake Tapper is on CNN Nightly. Michael Wolf is putting a lot of his energy into these books and also speaking circuit. So Michael Wolf is making a lot of money on these books with his proximity to Jeffrey Epstein. But with the death of Epstein, that's another reason why Michael Wolf, you know, clearly wanted to keep this information to himself, because the well with Jeffrey Epstein ran dry. So that's why Michael Wolf is scrambling now. He's falling into the space where people in the middle of a crisis fall into when they're trying to justify why they were doing the right thing. The rules only matter when they're convenient. Truth is negotiable, and relationships with power matter more than ethics, which really is the story of how Jeffrey Epstein got away with everything that he did for so many years now, why the media didn't touch the story. Wolf says he pitched these Epstein tapes everywhere to the networks, the publishers and streaming platforms and that everyone turned him down.

How many did you pitch and how many said no? Do you have any correspondence from those interactions?

I certainly do. And everybody has been pitched. There is almost no outlet. Streamers, networks, cable stations and book publishers who has not been pitched on this story. I was going to also everyone saying no.

He says they feared lawsuits from Trump.

I think the reason is that they are scared. They're scared of being sued by the Trump administration.

And maybe that is true, especially in light of how litigious the Trump administration is and the attacks against networks. Look what happened to Jimmy Kimmel. Look what happened to ABC and to cbs. But is there a simpler explanation? Wolf's own behavior contaminated his reporting. And maybe the news outlets were seeing that because you cannot act like a strategist for is not how credibility works, and it is not how journalism works, which is why the story matters. Now, Wolf is insisting the real story here is Donald Trump. And there's no argument there that Donald Trump is the central part of the story. But for people like us, if you're listening, I'm going to include you in my little world here. Politically, we know that he's right. People do want to know what Trump knew and what Trump did and what those emails reveal.

I'm not sure that they realize that the subject here is not so much Jeffrey Epstein, but Donald Trump.

We also like when the curtain is pulled back and it reveals something else. We know that Wolf's narrative here is saying it's vital that we understand who Trump is, quote, who this man is.

Because he is the model of. Of what a leader should be.

Of.

Of. Of what success looks like.

And there's the irony. To understand Trump, the public now has to understand Wolf. His methods, his choices, his boundaries, and the way he used messaging to defend himself when the emails became public. Because this truth is not just about Trump or Epstein. It's about the ugly truth of access. What money will bring you, what power will bring you. All the people who affiliated themselves with Epstein, all that is slowly coming out. But also, this is access journalism. When you stay close enough to the powerful long enough, you eventually start sounding like. Michael Wolff will keep insisting that everything he said to Epstein was just a part of journalism and that ingratiation is a tool, not a betrayal. And sure, reporters build trust. They earn access. They play the long game. I've worked in media my whole life on both sides. There's a time that I worked in journalism as well. I know a lot of reporters. My guy, he is a reporter. He is always talking about the people who give him access, who give him stories, who leak things to him. I mean, that is a very important part about journalism, especially when you are that type of watchdog journalist or an accountability journalist, which is certainly what Michael Wolff is. But Michael Wolff is so close to the flame, which is why he is trying to reframe, because there's a difference between getting close to a source and becoming a character in their strategy. And the emails show Wolf didn't just listen, he participated. And he wasn't just gathering information. He was helping a predator manage optics. He wasn't just observing power, he was advising it. That's the part that makes people recoil, myself included. This past weekend, I spent a lot of time listening to podcasts about Jeffrey Epstein going all the way back. And not only was this man a predator to young women, which will make your stomach turn, especially if you read the Wolf emails next to what Jeffrey Epstein did to women, but he also was a predator to people who invested in him. He was also like a Bernie Madoff that's getting lost in a lot of this. He was involved in a Ponzi scheme and lost a lot of money for retirees, and he got off free on that one as well. Jeffrey Epstein was dirty, dirty, dirty. And he always got through because people helped him. And that's the real concern. And for journalism, it comes down to public trust. The coziness, the power games, the moral corners of journalism quietly cut out. And that's an ugly truth in this entire story. It's the journalism piece. It's so disappointing. I spent time on my Live last week talking about Megyn Kelly, who was trying to explain the justification that Jeffrey Epstein only liked older girls and therefore it wasn't pedophilia. It was so disgusting to listen to her, but I don't even consider her a journalist anymore. She is purely a content creator out for money. But Michael Wolff is still acting as a journalist. And when a journalist decides that the end justifies the mean, once you start thinking that way, the audience stops trusting you. That's where I think Megyn Kelly's in that territory. Tucker Carlson's in that territory. It's former journalists who just become strictly content creators around a political ideology. You want the conservative audience, so you're going to say and do whatever it takes to get those clicks and to get those views. But when you're a journalist and you're trying to remain neutral, it gets a little gray for you. Because once the audience stops trusting you, you don't just lose credibility, you lose the ability to hold power to account at all. And that's what we've been watching play out here. Not a scandal about one man, but a case study. And what happens when the people tasked with telling the truth start operating like the people they're covering? That's all for this week on the podcast. Thanks for listening. Bye for now.