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- [00:02]
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Joe from Vanta
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- [00:57]
Harry Littman
Get started@vanta.com hi everyone, Harry here. We're coming to you a little early this week. Normally we'd publish the week's one on one on Thursday, but I wanted to share this conversation with you before the holidays. And I also wanted to give you my top line thoughts on some really big news we won't get to cover on the podcast until the new year, namely the Supreme Court's landmark ruling in the Trump versus Illinois decision that issued this week on Tuesday. It's a landmark decision not only because it shut down the administration's efforts to federalize National Guard troops in cities across the country Chicago, but Portland, Los Angeles, pretty much every place except Washington, D.C. which is on a separate legal footing. But also, and as importantly, because it rejects the administration's lead argument that the courts just have to defer without even reviewing Trump's emergency declarations, even when they're based, as these were, on flagrant falsehoods, completely untethered to the facts, in the words of Judge Immigrant in Portland. And the pivotal argument that the court adopted came from an amicus brief submitted by a Georgetown law professor and former DOJ official and friend of the podcast, Marty Lederman. Last month on the podcast, I talked with Marty about precisely the argument that swayed the court in this case. That episode is called the phrase that could End Trump's National Guard Power grab. And if you want a full breakdown of the argument straight from the professor's mouth, there's a link to that conversation with Marty in the show's notes. Now here's my Conversation with Chris Whipple on his interview with Trump Chief of Staff Susie Wiles. Welcome to Talking FEDS One on one. Deep dive discussions with national figures about the most fascinating and consequential issues defining our culture and shaping our lives.
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I'm your host, Harry Littman.
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Welcome to another Talking Feds one on one. I'm really privileged to be talking today to the journalist who shook up the Washington D.C. and the whole country this week, Chris Whipple, who published in Vanity Fair a tour de force two part story drawn from 11 separate interviews of Trump Chief of staff Susie Wiles. That among other things, promises to be one of the defining accounts going forward of Trump's second term, but is also a blockbuster story for today and next week. Chris is a journalist, documentary filmmaker, bestselling author with a real specialty in this in coverage of chiefs of staff. But for years, he's reported on some of the most powerful people inside American politics. He's the author of four books, including the how the White House Chiefs of Staff Define Every Presidency and has written for kind of every publication in the book. So, Chris Whipple, thanks so much for being with us on your big week.
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Chris Whipple
Yeah, thanks for having me.
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Harry Littman
I wanted to start in a sort of a more process way. How does something like this work? 11 interviews starting in January. You had to approach, I assume, not just Wiles, but the White House. How do you kind of negotiate out this sort of grand project?
- [05:01]
Chris Whipple
Well, you know what, Harry, I mean, every once in a while in a reporter's career, lightning strikes. And this was one of those times. And it was all Susie's doing. The White House was not involved. I don't know whether she told Donald Trump what she was doing. All I know is I dealt directly with her and her office. And then later in the process, when we had the photo shoot, which was a big production, as you can imagine, then that was a different story. Everybody knew what was going on. But up to that point, it began with a phone call that I made to her. It was January, 10 days before she began her as White House chief of staff. She was driving from Mar a Lago to her house in Ponte Vedra in northern Florida. We started talking, and I was immediately struck by how open and freewheeling and unguarded she was. Everything was on the record, as you know, with senior White House officials. That never happens. And yet here she was now in the very beginning. And so that was true for 11 months. And as you pointed out, 11 interviews, it was all on the record, except when we explicitly agreed otherwise which was very rare. She rarely went off the record. And yet she was amazingly candid, as you know.
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Harry Littman
And I gather some of the interviews were in casual moments. One when she's doing her laundry. I mean, she does seem to be very composed and broadly speaking, because there are some exceptions that we'll get to. Very aware of what she's saying and I think very strategic with a real sense of what she wants to say about the administration overall. Were you struck? You've talked to other chiefs of staff at her general unguardedness.
- [07:11]
Chris Whipple
Yeah, I don't know how strategic it was now. You know, I mean, look, she's been around and she's a savvy, sophisticated political operative. So yeah, you would assume that what anything she did over that period of time would be strategic. And yet I really am convinced that one of the reasons that she's so open and the reason this thing landed like a nuclear bomb this week is because she's in a bubble. Not so much. This is not the bunker of the Nixon White House, but it's a bubble in which they all speak this language and it's a crazy language. They talk about things like revenge and retribution. And she jokes with JD Vance about being a conspiracy theorist and apparently Vance has no problem with that. And I think that when you're in a bubble talking to acolytes for too long, I can only assume that she loses track of the fact that some of what she's saying sounds crazy to everyone in the real world. I can't help thinking that that's a big part of this.
- [08:24]
Harry Littman
Yeah, you know, it's a great point. And you look at that Vanity Fair photo shoot, very high gloss, very sort of high. And. And it does to me seem like everyone's a sort of different stripe of crazy, just objectively speaking. And she does stand out as the kind of sane one in the room. Now, the readership on Monday, when it first came out, were sort of Tuesday, actually. Yeah, yeah. I'm sorry. We're anticipating a hurricane Donald, as has happened before and. And yet, in fact, he seemed. Did the President perfectly okay with it, including some memorable lines, maybe the most. He's got an alcoholics personality. Did it surprise you because you say it hit like a nuclear bomb and yet not. Not at the epicenter of the bubble, as far as I can tell. They seem to have just. Yeah. Did that surprise you?
- [09:24]
Chris Whipple
No, didn't surprise me. Not in the Oval Office because there's a real bond that they have. There's a kind of magic that she has with Donald Trump. And of course, I write about it why that's the case, this extraordinary personal history she has with her father, Pat Summerall. And Trump was almost in awe of her the first time he met her. He was talking to the daughter of the great Pat Summerall. In his mind, that stuff that impresses him. They hit it off. And then she, as Rubio pointed out to me, she achieved this earned trust over years and years they've been together. And so I never thought that anything she said to me was going to blow that up. And sure enough, you saw all the wagons circle immediately and in defense of her, including people that she took shots at, like Pam Bondi.
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Harry Littman
Right. And, well, she took shots at many, but I think they know who's got.
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Chris Whipple
I never thought that Susie was headed to the woodshed with Donald Trump and the way David Stockman went to the woodshed in 1983 or whatever it was, and James A. Baker III, barely the chief of staff for Reagan, barely saved his job. Obviously, I was flattered that Peter Baker thought this was comparable in terms of being this huge story. And it is. But the difference is that there's nobody who could take Susie to the woodshed.
- [11:07]
Harry Littman
I also think it's fair to say everyone, understandably and predictably, goes for some of the red meat revelations. But, you know, the overall story takes a man, a president, who by the most sympathetic of accounts is not very strong on details, maybe doesn't work all that much, kind of has a improvised, improvisational way of doing the job. And I think she did sort of humanize it, even with this term alcoholics personality, which he embraced since he doesn't drink. But, but the notion of, oh, I, you know, just always going for it, think you can do whatever you like, et cetera. So I think in the broad, you can imagine that she had her eye on a more, you know, sympathetic account of Trump. I did want to ask this. Over the course of these 11 months, the administration has, you know, taken a lot of hits, including in areas she discussed. And they are at arguably a low ebb, as your conversations accrued. Was there any sense of her trying to, you know, knowing that they're in a little bit of defense and trying to push back or trying to put on the best footing what has been a rough kind of patch. How did things change over the course of the 11 months?
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Chris Whipple
Yeah, we talked about political challenges and some of the landmines, some of the dangers ahead between now and the midterms. And she talked about the Epstein challenge, and she admitted that she just totally underestimated it as a problem, as a political problem. And so she said Pam Bondi whiffed in her handling of it, but in a way, she did, too. I mean, she underestimated it. And she, she, so we talked all about that and we talked about the fact that she, she feels that the president needs to start talking less about world peace and much more about the domestic economy. She knows that's a challenge. And yet again, I spoke about the bubble. I think that, you know, you, if you ask her about the 2026 midterms and how they'll do, her answer is, we'll win the midterms. Now, that's a pretty bold statement when you consider that historically, incumbent presidents get shellacked, in Barack Obama's phrase. And J.D. vance was frankly, way more, seemed way more realistic. I asked him how they do and he said, well, look, an incumbent party can lose 13 seats in the House and maybe two or three Senate seats, and I think we'll do better than that. Well, now, that sounds like Vance trying to lower expectations. Right? But boy, they were poles apart on that. And I think there's some, I think even with a savvy political operator like Susie Wiles, there's some magical thinking going.
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Harry Littman
On that's really interesting. And of course, I think part of this is the role she assigns herself as chief of staff, the first woman to chief of staff. I'm not the chief of you. You memorably quote her as saying to the president, and you think of previous chiefs of staff whom you know better than anyone probably in the world. And there is the sense of a kind of testosterone fueled rivalry in the White House and chiefs of staff trying to push, I think of Rahm Emanuel, say, trying to push forward certain policy. And she really styles herself a kind of facilitator, as you say. Sometimes she changes her mind, sometimes she says things are, you know, she was wrong. So I just think that reconceptualization of the job is probably instrumental in her very tight in the trust that Trump obviously places in her.
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Chris Whipple
Yeah, well, I think, look, there's nothing necessarily wrong with, with wanting to advance the president's agenda. I mean, that's her job and it's not her job or any White House chief's job to advance any particular policy. You know, Jim Baker under Ronald Reagan took a lot of flack for being the quote, unquote, pragmatist.
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Harry Littman
Right.
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Chris Whipple
You know, because all the true believers, the Let Reagan Be Reagan gang hated him and tried to gang up on him and Baker was too smart for them and savvy. But. So, look, I think she fancies herself, I think an honest broker, which is a good thing. But the real challenge for her and the real weakness, in my view, is that she quoted Jim Baker, that Maxim, I'm the Chief of Staff, not the chief of you. But what she leaves out is the most important part of the job, which is walking into the Oval Office, closing the door, and telling the President what he doesn't want to hear. That's what Baker did when Reagan wanted to go after Social Security right out of the blocks. And Baker sat him down and said, Look, Mr. President, Social Security is the third rail of American politics. You touch it, you'll be electrocuted. And Reagan pivoted to tax cuts and was reelected in a landslide.
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Harry Littman
Yeah, this feels like the kind of White House that people are especially worried about telling him stuff he doesn't want to hear. Okay, let's pick up on a few things that she offered up. And I don't know if you consider these particularly unguarded moments. I think they certainly play into not just a sort of controversial image of Trump, but some real defects that his detractor sold. So you mentioned Epstein. She said, it seemed very casually yo this comment. He made assertion, he made that. That Bill Clinton had been down at Epstein's island in Florida. He made it up. That struck me as a pretty stunning thing to say about one's boss and the President. If you'll make that up, what won't you make up? And with a president who has such a checkered record of veracity, that's a pretty big breadcrumb to drop. Did it seem like a sort of slip or things like that were that kind of candor? How does it fit into the overall mission of these 11?
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Chris Whipple
Like, it didn't feel like a slip to me. It didn't feel like something she said inadvertently. It seemed like something that she considered not a big deal, that Trump would go around saying, as he did, that Bill Clinton had been to Epstein's island supposedly 28 times. That's what Trump said. And then she tells me, I've read the Epstein file, as she calls it, and Trump's all over it. And, yeah, you know, he was. I know it's a passe word, but they were playboys together, running around in, you know, southern Florida. And then. And then she goes, guess who's not in the file? Guess. Bill Clinton. I mean, not absent from the file, but nothing really incriminating. And she said, no, there's no evidence that he didn't go. No evidence that he went to the island despite Trump having said all this. And it was all very matter of fact.
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Harry Littman
That's so interesting.
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Chris Whipple
Stunning.
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Harry Littman
It sounds like a pretty important lie to me. But I guess one way of thinking of it is, you know, if you want to build some kind of credible case for Donald Trump, you can't pretend he always tells the truth. Maybe that's part of it. Let me go to the another thing that some people have noticed, but as a former DOJ alum, I found absolutely gobsmacking. Yeah, retribution. And not just that. Well, she knew it would happen, so she tried to strike a bargain. Let's just do it in the first 90 days. The it in question, I'm sorry, is violate the Constitution and your oath of office and bring prosecutions for inappropriate reasons. And moreover they she tries to do this deal with him and in fact he doesn't stick with it. He keeps going. After those 90 days, which she explains as well, opportunities arise. Now, to me, that really is one of history's greatest accusations against Donald Trump. And she seemed again to just kind of demur. Yeah, yeah, that kind of happens. Do you think she's a non lawyer, Right. That it just didn't hit home what a serious kind of concession that was?
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Chris Whipple
I do. I think they're living in another world again. They're living in this bubble with a different set of priorities and values. And this came up kind of out of the blue. I just sort of, I didn't have any reason to expect her to give that answer, but it just seemed to me I wanted to ask the question and I did. And I simply said, susie, look, do you ever go into the Oval and just say to the President, maybe we should cut out this revenge and retribution stuff and govern and instead govern, focus on securing the border and bringing down prices. And she said, and I don't know, maybe because it sounded so reasonable, she just said, yeah. She said, I have had that conversation and we have a loose agreement, as she put it, that he'll end this stuff after 90 days. Anyway, we talked a little bit more, moved on, and then months later, obviously the, the revenge and retribution campaign was gaining speed and it just kept going. And months later I said, remember when you told me about 90 days that this stuff would be over? She said, well, yeah, but it's not really a retribution tour. And so I pressed her on that and I said so. And then she started to say, well, look, he doesn't get up in the morning thinking about retribution, but when the opportunity arises, he'll go for it. And then I said, so what about. So all this talk about Letitia James and mortgage fraud. And she said, well, yeah, okay. Well, that's okay. That's retribution. And to me, I'm not a lawyer, but, boy, to me, that sounded like a get out of jail free card. For Letitia.
- [22:34]
Harry Littman
Well, there is that. I mean, I think she already had some other cards, but there is that sense, I think. So you're. You posit that it's what comes from being in a bubble, but the kind of. Well, okay, I guess so when it. When it really is, you know, one of the sort of first counts in any. Any of history's indictments. There are other things like that. It's also interesting. I wanted to move to a couple other figures in the administration. You said nobody. I mean, maybe they're licking their wounds privately, but. But nobody has come after her. I was really struck by some of the things she said and actually by the picture shoot itself involving JD Vance and Marco Rubio, who would be, I think, in most accounts, the heirs apparent to the, you know, Trump MAGA crowd. And although Rubio deferred after this to Vance, she seemed to basically say, they are two different people. One is someone who stays to his principles. That would be Rubio. And one is. And this is the same kind of. Well, okay, I guess he made a complete political change over to capitalize when he was running for Senate. This would be his conversion.
- [24:01]
Chris Whipple
Vance's conversion, by contrast with Rubio, was sort of political.
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Harry Littman
Right. Yeah, well, well put. But I. But I think fairly damning. And I'll just add one little nugget that wasn't from her, but from the story is when they're having the picture shoot and Vance says to the photographer, 100 bucks for. And he didn't say to make me look good. 100 bucks for everyone else you make look bad. And 1000 bucks if you do it to Rubio. Ha, ha. But such a. Such a vantage point, a flashpoint on the kind of natural rivalries within the White House. Yeah.
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Chris Whipple
You know, I gotta say, Harry, actually, you know, I was there for the whole thing. And in my view, you know, Vance is, you know, he is kind of a joker and a. And a, you know, kind of a back slapper. And he. And he likes to crack wise. And I honestly took that as him just kind of needling Ruby. I didn't see any, you know, any kind of anything weightier than that. So, you know, and he. And he Made crack jokes about a few other things. I mean, the photographer explained that he was using old school, he was using film as opposed to a digital camera because it, you know, it gives the subject soul, as he put it. And Vance goes, oh, well, Vanity Fair once wrote that I have no soul. So I guess that's a good thing. And that's fair enough. And that's kind of his personality. Yeah.
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Harry Littman
And by the way, I want to say, fantastic pictures. Seriously, there is something that really is vivid about them. Okay. You know, speculation. A normal kind of, you could say half life or whatever of a chief of staff might be a couple years or, you know, that's when someone would leave. Did you get a sense that some of her candor and unguardedness was preparatory to, you know, her actually kind of leaving sooner rather than later?
- [26:10]
Chris Whipple
The answer is no. And I think there are two likely outcomes. I think she'll stay through the midterms, barring some unexpected, you know, thing. Maybe there's some internecine thing going on that we're not aware of right now within the west wing. And she's in trouble, but I don't see any sign of that. Assuming that Trump's okay with her, I think she's gonna stay at least through the midterms. But I wouldn't bet against her staying through the whole term, as you pointed out. I mean, as you know, I've studied this for a while. I mean, the average chief of staff lasts about 18 months. Andy Card set the record under W with, you know, more than four years. That's the range. But, boy, I wouldn't, I wouldn't bet against her staying for the duration.
- [26:59]
Harry Littman
And by the way, so, you know, I think one could say about some of these tart comments, it seems partly her style, maybe to make them personally. Like, you know, she was pretty tough, as you say on Bondi. But I assume if she's an effective chief of staff, she gives some of that bad news kind of face to face. And in her perhaps kind of politic way, she's a bit of the enforcer. For Trump, who is considered by many to actually shy away from conflicts, notwithstanding his braggadocio, did that kind of aspect of the, you know, the whip cracking chief of staff in a, in the guy, you know, in a different way, the first woman, et cetera, of. Come through.
- [27:47]
Chris Whipple
Yeah, you know, it's, it's. She was. There's a great story, I, I think a behind closed doors story of, of how she called Musk, Elon Musk on the carpet over his destruction of usaid. He burned it to the ground. And she was, she was like kind of, she minced no words about Vance. I mean, she said, yeah, you know, this guy, he's no, no, duck. And he came in here and did that. All he knows how to do is burn stuff down. And he did it. I was aghast. Another word she used. So I think they probably had some, as the diplomats used to say, fruitful exchanges. But with others, I don't get the sense that she ever loses her stack. I think she's, by all accounts, very common. My experience with her, I never saw her angry. She was always even keeled. I think that's the way she is in the White House. And I think that. And she's very popular. I mean, people do like her. So this is not a Rahm Emanuel or a Don Regan or a John Sununu by any means. I think she's well liked.
- [29:04]
Harry Littman
And so I think completely instrumental in whatever kind of role Trump has been able to have as president. So much here. And of course, as you say, Peter Baker mines it very quickly. We have the 3, 4, 5 headlines. But these are two long, very, very rich stories.
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Kudos to you.
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But is there a part of it. You've been very much on the, you know, media tour in this week that people missed, you think, and you're expecting maybe on the second, third, fourth look to, to, to really have, you know.
- [29:41]
Chris Whipple
What, you know, what nobody, you know, what nobody has brought up at all. And so on the time I was, I was at, I had lunch with her in the White House on November 4th, she's just come out of the Oval where she's, they're talking about blowing up boats in the Caribbean. And, and we're sitting there, and I, and suddenly occurs to me that we're sitting not very far from this gaping hole where the East Wing used to be. And so I said to her, were you surprised by the ferocious reaction when this happened? And she said, no, we weren't surprised. We expected that. And he wanted to go ahead. He just wanted to go ahead and get it done. He has absolutely the right to do it, blah, blah, blah. And then she said, but I think you should wait until you see the changes in their totality because he's, he's got a bunch of other things planned. And I said, like what? And she said, I'm not telling. He clearly, you know, just, just enjoyed teasing me with that and leaving me hanging. But God only knows what, what other renovations Trump has already got, you know, on the drawing board that he hasn't told anyone. No one's brought that up, but.
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Harry Littman
Right, right. Well, I'm glad. So glad you did. Oh, that's just Donald and his little plans. Okay. Hey, Chris Whipple, thank congratulations on a story that I think is going to matter not just this week and next, but really throughout history as people study this administration. Really a tour de force. Fantastic reporting by Chris Whipple and really appreciate spending some time with us today.
- [31:25]
Chris Whipple
Thanks. Thanks so much for having me. I appreciate it. Good to see you.
- [31:31]
Harry Littman
Thank you for tuning in to One on One, a weekly conversation series from Talking Feds.
- [31:37]
If you like what you've heard, please tell a friend to subscribe to us on Apple Podcasts or wherever they get their podcasts. And please take a moment to rate and review the show. You can also subscribe to us on YouTube, where we are posting full episodes and daily updates on top legal stories. Check us out on substack harrylitman.substack.com where we're posting two or three bulletins a week breaking down the various threats to constitutional norms and the rule of law. And Talking Fez has joined forces with the Contrarian. I'm a founding contributor to this new media venture, committed to reviving the diversity of opinion that feels increasingly rare in today's news landscape, where legacy media seems to be tacking toward Trump for business reasons rather than editorial ones. Rest assured, we're still the same scrappy independent podcast you've come to know and trust just now linked up with an ambitious and vital project designed for this pivotal moment in our nation's legal and political discourse. Find out more@contrarian.substack.com thanks for tuning in, and don't worry, as long as you need answers, the Feds will keep talking.
- [32:59]
Talking Feds is produced by Luke Cregan and Katie Upshaw, associate producer Becca Haveian, sound Engineering by Matt McArdle, Rosie, Dawn Griffin, David Lieberman, Hamsa Mahadranathan, Emma Maynard and Hallie Necker are our contributing writers. Production assistants by Morgan Chisholm and Akshaysh Turbailu. Our editorial interns are Bridget Ryan and Troy Neville.
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Our music, as ever, is by the Amazing Philip Glass. Talking Feds is a production of Delito llc. I'm Harry Littman.
- [33:38]
Talk to you later.