Madeleine Westerhout: "My Dream Job At The White House, How I Lost It And What I Learned"
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Alright, today on Live in the Brain, we have a very unique guest. You may remember hearing a little bit about her story in the headlines, and you'll certainly remember as we began talking to her, and you may have wondered what happened to her. Her name is Madeline Westerhout. She was executive assistant to the president, President Trump, and the former director of Oval Office Operations as well. Kind of a gatekeeper, really, about who would see the president and who would not.

And it all came to an abrupt halt in something that captured headlines. When she was a part of an off-the-record dinner, and somehow part of it went public, she's got a brand new book out called Off the Record, My Dream Job at the White House, How I Lost It and What I Learned.

Madeline, welcome. Hi, Shannon. Thank you so much for having me. This is my first podcast, so I am very, very excited. Okay. I'm going to call it a podcast exclusive. Great to have you with us. I haven't gotten through the whole book, but I've gotten through a good chunk of it. And there's so much inside scoop for people who wonder about the different personalities who have been through the White House, how it worked, how they clashed. But most importantly, let's start with your story because I can't imagine as a young woman in your 20s,

Going through something like this. I think we've all made mistakes that have made us cringe and feel like oh my gosh I'm never going to come back from this

And I got to imagine that was your experience, had a little bit of that, but you got the whole world watching in your case. Tell us what it was like to go through that and what happened. Yeah, absolutely. So I think, like you said, like many people, I made a mistake and I had a lapse of judgment that cost me my dream job. And so what happened was I, after, during a kind of rare day off, I, I,

was laying by the pool and had a couple of drinks and accepted an invitation to what was supposed to be an off the record dinner with four reporters and a White House colleague of mine. And at that dinner, I said some things that I didn't mean and that I never should have said. I take full responsibility for my actions and I deeply regret hurting the people that I cared about so very much. But I really just wanted to share with people that

kind of the process of how this mistake happened and then the fallout of it. And I think like

Like you said, a lot of people make mistakes and mine just happened to play out on the world's largest stage. So it was, it was pretty brutal for a while. Absolutely. And one of the things I thought was so unique about your situation is almost immediately the president had kind of things to say about you. I mean, it wasn't a positive for him or for you or for his family, how this whole thing went down. But he, you know, pretty quickly said she's a good person. You know, she had a bad night.

And he has not been that way with a lot of people. I'd say the vast majority of people who left the White House. And so it sounds like even in this mistake, he really was forgiving of you. And he has been brutal to other people who he has felt have betrayed him, not done the job he wanted at the White House where they ultimately clashed. Were you surprised by that? Or did you expect that's kind of the way that he would treat you even, you know, in the face of what had happened?

Yeah, I don't think I expected forgiveness from him, but it was really, really important for me to call him right after I was let go and apologize directly to him. And so the fact that he was so gracious and able to forgive me really helped.

falls in line with the man that I got to know. And so I am so thankful that he forgave me right away. And one of the things I talk about in my book is actually how long it took me to forgive myself. And that was kind of the process of writing this book was very, very cathartic for me. And finally, right when I was about finished writing the book, I realized I wasn't going to let one night and one mistake define me.

And then I was finally ready to forgive myself. But I don't think I could have gotten through it if the president hadn't been as gracious as he was.

Yeah. I mean, because like you said, sometimes the hardest thing about making a mistake is forgiving ourselves and processing it because, you know, you talk about how you would think about it every day. And there were times like every minute of the day, because of course, when your whole life is on display for the world to see, um, it's really tough. And a lot of people crumble. I mean, and even if you had moments of that, people would certainly understand, as I said, to be a young woman in your twenties and have the whole world know about you losing your job and why and being so high profile. Um,

where did you kind of draw the strength? Was it family? Was it faith? Was it friends? Did you have a period where you thought, I don't know how I'm going to come back from this and what got you past that?

Yeah, absolutely. You know, there were some days for a while where I didn't get out of bed. I just felt like I lost my job. I don't really, there's nothing to do. I don't have anyone to talk to. And it was really, really very difficult. But I was very fortunate to, I went back to California for a while where I'm from. And I spent a lot of time with family and my family and my friends were, were so caring. And

that I received from so many people after this really helped me get through some of those difficult times. And I also, I did a reconnect with my faith. I think in Washington, DC, it's very typical to kind of worship these false gods, which are, you know, power and proximity to power and titles and salaries. And so when that was stripped away, I was able to kind of refocus on what was important and that's family and friends and my faith.

So where do you go from here professionally? You've got the book out now. And again, to remind people, the name of it is Off the Record, My Dream Job at the White House, How I Lost It and What I Learned by Madeline Westerhout. What do you see for yourself professionally moving ahead? Because I got to say, America is one of these places that really is all about second chances and rooting for people to come back. We've seen it with celebrities and politicians and all kinds of people. Yeah.

America loves a comeback story. They do. And so I wonder what you feel like your next chapters will be. You know, I'm, I'm still figuring that out. Working on the book took up, it was really a full-time job. And so now that I'm finished with it, uh, which today has just been such a whirlwind and it has been such an exciting day. Uh, I, I want to get my message out to as many people as possible. I think there's, there's multiple layers to this book. Uh, obviously

obviously, you know, it's a political story. And so I talk very highly about my relationship with President Trump. But there's also that human human interest story, which is people make mistakes, and how do you overcome that. And so I think for the foreseeable future, I'm going to just focus on, on getting that message to as many people as possible. And then from there, you know, the great thing about this country is there's so many opportunities. And over the past almost a year now,

I've been able to think about what could be next. And I don't know if that means going back to school and college, but before I was a political science major, I was a psychology major. And so I thought maybe going to get my master's in psychology. So lots of options and I'm really excited and really looking forward to kind of everything that comes out of this.

Yeah, and one of the things that is getting a lot of attention in the release of this book is the fact that you say you were working on RNC staff for the party, and you didn't actually vote for President Trump.

Can you believe it? Well, I mean, it's interesting. But I think there were a lot of people who back in 2016, who were, you know, openly saying as Republicans or conservatives, I don't know if I can vote for this guy. I don't know if he lines up with where I'm at. So I think there were other people who felt the way that you did too. What's changed your mind? Because you say now this time around you're voting for him.

Yes, absolutely. So it's interesting. This was one of the things that I thought a lot about whether I wanted to put in my book or not. And I decided at the end of the day, I'm going to be so honest and vulnerable in this book. And that includes admitting that I did not vote for my former boss. And I actually called him last week to make him aware of that because I wanted him to hear that from me. It was really important for me.

that he heard that from me directly. And so before the election, you know, I had never met President Trump. I had never spent any time with him. And my opinion on him was based entirely on what I saw and what I read in the media. And it wasn't until I got to meet him and got to know him so well that I was able to actually make an informed decision.

which is that Donald Trump is a kind and gracious man. He is a good boss. He is a strong leader. And the more I got to know him, the more I respected and admire him. And I hope people can read my account and kind of question for themselves what they hear in the media and take a step back and make decisions based on fact more than just what they see on TV.

Yeah. And you talk about the fact that by your accounting and your experience, you think that he is respectful of women, that he is, he promotes women. And you know, what's out there. I mean, he is somebody who goes after folks. He'll talk about their personal appearance. He will insult them. He will write them over the coals.

And so, you know, you have a lot of people across the political spectrum who think he's not especially respectful of women. They'll bring up his infidelity and all kinds of other things. So how do you feel about making that argument when people will say, listen, there's a lot of information and evidence on the other side of this argument that they think doesn't bear that out for him personally?

Sure. And of course, that's valid. I think people are, of course, entitled to their own opinions. And what I experienced was someone who, like you said, respects women and promotes women, surrounds himself with really strong women. And once I got to know him, I realized that the opinion that I wanted to make of him needed to be based on what I experienced. And so I kind of

took everything that was said by him or by others in the past and took it with a grain of salt and just focused more on the man that I got to know and what I witnessed every single day, which was someone that respects, like I said, respects women, but also really surrounds himself with

with women that he wants to take their advice and he listens to them and he promotes them. And just as actually a major champion for women. Well, it is interesting when you look at people like Kellyanne Conway and others who have been, you know, highlighted and used throughout the administration, employed and put in key positions, you know, that, that I think that there is a lot to be said for the fact that he doesn't seem to be afraid of strong women. He's raised a couple of them, a bunch,

And he's married to one.

don't want themselves to be in the spotlight. The kids, the spouses, I think they're very much more about, I'm not the president. Here's what I'm working on over here. They don't want to be in that white hot spotlight. I think most of them don't. I mean, there are some exceptions to that role, but she is very much, and you will talk with her and see that she's very much got her own opinions and very much is not afraid to share them with the president. And I think that people may not get that dynamic in their relationship, but it's definitely there. Yeah.

Absolutely. Yeah. He definitely listens to her. And she's got plenty to say. She does. She is. She is a remarkable woman. And she's funny too, for people who don't know her sense of humor. And they disagree about things. And I think that's like any married couple, you know, they're in a fishbowl in a place that I think most married couples wouldn't want to be under that level of scrutiny, but it's working for them. And we'll leave it at that. We'll have more live in the Bream in a moment.

The Will Cain Show is now dropping five episodes a week. Join Fox & Friends weekend host Will Cain as he tackles the latest headlines from his unique perspective, along with thought-provoking interviews with leading figures and live calls from viewers and listeners. Listen wherever you download your favorite podcasts. Okay. I thought it was interesting, too, that you said being there and being on the inside and living inside this bubble is...

there were times that you'll look out in the press, media, and I think you said 80% of the time you'll see something and say that's not actually an accurate account of what happened or what is actually going on or who was there or what was said. Was that surprising to you? Because a lot of people will say, listen, it's not surprising that you would get negative press on certain policies that people disagree with, that kind of thing. But are you saying that there were conversations or things that were completely false, fabricated?

What are you saying with that 80%? Yeah, I think there were some times where I was sitting at my desk and behind my desk I had a TV that had four channels on it. And one of the channels would be reporting, you know, President Trump is berating his aides. And I looked into the Oval Office and he's sitting there quietly, you know, reading the paper. And so it was very confusing to me kind of where these people got this information. And so there's stark examples like that. But then there's also a lot of examples like when –

the president was making decisions and the press reports that he wasn't making informed decisions. And so it was just really fascinating. And one of the reasons I wanted to kind of

write this book was because I felt like if I was sitting right outside the Oval Office and I so easily believed what I was seeing in the news, then I'm sure other people did. And so just kind of taking a step back and kind of thinking like, I'm not sure that everything you see in the mainstream media is absolutely true.

I think that's true. I mean, I think some of it has been disproven and later not played out. And you never know if the people are getting sources that are feeding them information that isn't correct. They rely on it. And it's hard when we have so many unnamed sources and so many pieces now and that people so heavily rely on them. And we as journalists have to be careful about that. Either you trust your source or you don't. We have to vet our sources too. And sometimes they give you information that's not accurate. But you talk about,

you know, a lot about the personnel issues inside the White House too. And, you know, how people clash or get along with the president or don't or how they fall in and out of favor. So what do you make of those who will say, gosh, there's so much turnover in this White House and he can't keep the staff together and he loves someone that he hates them. They get along, they don't get along. You know, what do you make of the way that's been characterized in public?

Yeah, I think there's a couple of things there. I think for one thing, I think this White House has been covered more than any other administration. And so I am sure I don't have statistics in front of me, but I am sure that there has been a lot of turnover in previous administrations. This one just happens to be under a microscope. And the other thing that I will say is working in the West Wing.

is it's a very, very small environment. And so it's kind of like working in a large house. I mean, it is working in a large house, but working with family that you become very, very close with. And there's going to be days that where you don't get along with someone. And I think that's very, very normal. But overall, I think the president has a great team right now. You know, I haven't been there for almost a year, but from what I can tell, I think he's, he's got some people back, which has been really refreshing and, uh,

I'm sure he's surrounding himself with people that he trusts and that he knows has his best interests at heart. You talk about how it's easy to get sucked into the whole power play situation in D.C. and having lived here for...

Gosh, I forget how long now, but you know, 15, 16 years here in the DC area. You know, when I leave and I'm at home with my family in Tallahassee, Florida for a few days or my in-laws out in Pennsylvania, just with, like I say, normal, real good, you know, American people. There's a whole different world out there and it's so refreshing and calming and reassuring.

But DC is a, I mean, it is one of those things where everybody thinks they're the most important person in town. Everybody's in a hurry. Everybody's got an agenda. There's a lot of ego. There's a lot of power tripping. Um, and it can be very unhealthy. I mean, was that part of your unwinding when you left, um, the way as we like to call it and, and just hang out with people who are not in this day to day rat race and power struggle? Yeah, absolutely. Politics is, is not for the faint of heart. And, um,

And when I left, one of the things that I loved about being able to go back to California was in D.C., I kind of felt like I had a scarlet letter on my chest and that everybody knew who I was and what happened to me and what I did. And then I left and people had no idea. And, you know, I never for a minute thought that I was dead.

so important that the whole world knew my story, but DC is a bubble. And so when I left, I kind of was able to realize like, this isn't going to define me and this isn't who I am. And I was also kind of able to take a step back and look at how I treated people. You know, I was in a position with very close proximity to power. And I admit that I got sucked up in that. And

And, um, now that I'm out, I can kind of reflect back and, and think about how I treated people and how I wished I would have done things differently, but it's, uh, it

It's a crazy world in Washington, D.C. It is. And I think perspective is always good when we can get out of here and take a little break. It's always a good, helpful, refreshing kind of thing. I'm going to ask you, you know, what would be your message out there to somebody else, regardless of age, if you feel like you've blown it in a relationship or a job?

It's different as we've talked about and, you know, painful and on a number of different levels when the whole world knows what's happening with you. But, you know, there's so many people who feel like they've really blown it and can't put their lives back together. You're in a tough place trying to forgive themselves, constantly reliving. And you talk about the what ifs too. I mean, there's so many questions you ask. What if I hadn't gone to that dinner? What if I had gone somewhere else? What if I had said no to the invitation? What if I didn't say those things?

Um, what would be your message of encouragement for somebody who's in a really tough place right now? Yeah, absolutely. I think my message is that there are going to be bumps along the road. That's inevitable. We're all human. We're all a work in progress. Uh,

But I would say, you know, don't let one mistake or one bad decision define you. What I have learned is that every single mistake that I have made, and not just in this position, but, you know, as a human being, mistakes in high school and college and with relationships and whatnot, like every single mistake is a learning opportunity. And some are going to be a lot harder than others. And there's this, I don't know if this is a cheesy quote, but I love the quote, like when God closes the door, he opens a window. But if that window hasn't been opened yet,

enjoy the time in the hallway for a while. You know, there's just, you don't have to let one mistake kind of bring you down. Yeah. You've come out the other side of something that was a huge PR situation for you. And it sounds like you've been able to process that and come to a healthy place. And hopefully that will encourage other people. So folks who need that message will be

I'm very inspired by your book. And if they want inside scoop, there's a lot of that in this book too. It's called off the record, my dream job at the white house, how I lost it. And what I learned, um, by Madeline Westerhout. Uh, thanks for joining us. Your first podcast interview on the book.

And keep us updated on where you go from here because I think a lot of people will be rooting for you and encourage that regardless of the situation that you can turn it around and make the best of a bad situation. As you said, we always learn from our mistakes. We at least have the opportunity and it seems that you have as well. So Madeline, thank you for being on Living the Dream this week. Great to have you. Thank you so much, Shannon. I had a great time. Talk to you soon. Okay.

Hi, everybody. It's Brian Kilmeade. I want you to join me weekdays at 9 a.m. East as we break down the biggest stories of the day with some of the biggest newsmakers and, of course, what you think. Listen live or get the podcast now at BrianKilmeadeShow.com.