Alyssa Mastromonaco on Her Career and Memoir

Michel Martin sits down with the youngest woman to serve as White House Deputy Chief of Staff, Alyssa Mastromonaco, to discuss her new memoir, career and the new class of women making waves in Congress.

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MICHEL MARTIN: Alyssa Mastomonaco, thank you so much for joining us.


MARTIN: Your second book “So Here’s the Thing”.

MASTROMONACO: “So here’s the Thing”.

MARTIN: “Notes on Growing Up, Getting Older, and Trusting Your Gut”, this is actually your second book.


MARTIN: First one was a best seller, so how does former presidential scheduler, director, international traveler gal decide to write a book about basically how to do your life?

MASTROMONACO: So after the first book, the response was a little bit different than I thought. I thought it would be mostly like, oh, we miss and love Barack Obama, which of course part of it was, but a lot of it was response to some of the stories that I was telling, some of the more vulnerable, TMI stories. And so, as the sort of year or two went on after the first book, I kept a list of all the things that young women wrote to me that they wanted to hear more about, sort of like underserved topics. And so, low and behold they wanted to hear more, and I went even more TMI on this one. And it seems to have worked out. People seem to be enjoying it.

MARTIN: You really put it out there in a way that I think people do know you then obviously they’re not surprised, but –

MASTROMONACO: Yes. They’re like, “there she goes again.”

MARTIN: – for people who think about women in politics as having to be very buttoned up, very controlled, kind of keep everything to yourself, in some cases not really acknowledge that they’re women. And I wondered in a way were you like pushing against that?

MASTROMONACO: I was. I was because I always felt that I didn’t see myself. You know, in any sort of walk of life, people are drawn to professions or things where they see themselves reflected, like where they see a possibility of belonging. And so, I didn’t really see that for myself, so I stuffed myself into Spanx, I wore pencil skirts, I wore button-down shirts even though I had like a terrible sweating problem and always felt like you can see me sweat. And so, I decided, you know, the more comfortable I got the most I pushed the boundaries within the White House and the more President Obama had no problems with it. First lady had no problems with it, so I dressed a little bit more like myself and I found that I was more comfortable. And the more comfortable I was, the more comfortable people were coming to ask me questions. And so, I really sort of like, you know, after the first two or three years started finding my groove. If you look at the time lapse of photos, I definitely started looking a little more like you see me now towards the end.

MARTIN: I don’t remember seeing the poncho and the denim shirt and the quads, but —

MASTROMONACO: There was no poncho, there was no denim shirt, there were a lot of pantyhose. There was actually a website or blog back then dedicated to how, when Nancy-Ann DeParle, who was the deputy chief of staff for policy, who was the architect of the Affordable Care Act, when she and I were both elevated to deputy chief there was a blog dedicated to the shoes and clothes that we wore and it was not positive. It was like, these disrespectful women, they should have high heels on, they should have pantyhose on. And at first we were really nervous because we didn’t want to reflect poorly on the president. And so I mentioned it to him once and he was like, what do I care. And I was like, OK, great, thanks. Because you know, you don’t want to reflect poorly on your boss, especially he’s like the first African-American president, you don’t want people thinking he has these like children working in the West Wing.

MARTIN: If you could just pick one story from, say your international travels, that — what you really learned, something important.

MASTROMONACO: Oh my goodness. An international travel story.

MARTIN: I just can’t even pick out —


MASTROMONACO: Well that was —

MARTIN: — you were being spied on or where you realized that there were cameras in the shower or —

MASTROMONACO: Well that was —

MARTIN: — or jewelry’s on the desk, that you were like, what?

MASTROMONACO: Well everything really was — I think in terms of, like, a preparedness — because foreign travel in so many ways is about preparedness. Like even on my book tour last week I did five cities in a carry-on bag. Because you know what do you not want? You don’t want your luggage to get lost, you don’t want to have to go scramble. And so at the White House that was for the most part how we traveled. But once the president wanted to do me a real solid and knew that I would die to see the inside of Buckingham Palace. But we were not intend to go to Buckingham. Most of us were going straight to the airport because we were leaving. And so Reggie Love, then his personal aide comes to the door and he says, boss, boss wants you in the car over to Buckingham, take the helicopter Marine One over to the airport. And I started negotiating with Reggie. I was like, but I’m in jeans and a blazer. And he’s like, that’s a personal problem, what do you want me to do about it. And so I asked the valets who were members of the military — I’m like, let me carry some of the stuff so that I can hide what I’m wearing. And they’re like, get away from us. And so we end up in Buckingham Palace —

MARTIN: You’d think they’d have the nuclear codes —


MASTROMONACO: They had everything. They’re like stop, and —

MARTIN: — so maybe —

MASTROMONACO: They’re like, you’re not touching any of this. And so we get to the drawing room — we’re at Buckingham Palace, we’re in the drawing room, I’m so nervous, I’m standing behind a couch so you can only see — actually, it may have been this exact shit because I’ve had it for 100 years — and my blazer and not see that I have jeans on. We walk out the back of Buckingham, all the house staff is there, they’re waving goodbye to us, we get on Marine One, the president is like very proud he’s done something so nice for me and he turns around and he’s like, jeans, Alyssa? Jeans? And I said, I know, I know, I’m sorry, I didn’t think we were going to be going. And then he just looked back and he goes what’s in your hand? And in a effort to not look like I was totally fidgeting, I stole a copy of The Tatler from Buckingham Palace. So I’m sitting there on Marine One and he and the first lady just looked at me and they were like stop it. So the point was, though, never did I ever wear jeans ever again unless we were on–

MARTIN: I was going to say, so is the moral of the story don’t wear jeans ever? Ever?

MASTROMONACO: Don’t wear jeans — if you’re working in the White House, just save the jeans to for when you know you’re already going where you got to be. Like don’t — don’t — don’t do the transit jeans or casual clothes because you never know when the — you’re going to be in the presence of the queen.

MARTIN: Obviously Barack Obama’s the first African-American president of the United States. Was that like a part of your consciousness —


MARTIN: — always when you were there?


MARTIN: In what way?

MASTROMONACO: I think there were a couple things. One, you didn’t want to be — you knew the scrutiny was going to be different. You know, I think that — or even if it wasn’t, you thought it might be. And so you wanted to be at 150 percent every day, because you never wanted the real dark side of the right to say, see, this is what happens when you give people who look different than past presidents a chance.

MARTIN: Was that ever communicated to you or —


MARTIN: — was that just something in the air?

MASTROMONACO: Just something that I felt personally that I wanted to make sure that I did my best every day. You know, and there is a generation of kids who will never know a time when there wasn’t an African-American president and like, how important is that? Like, imagine when, you know, we have our first female president and there will be kids who are like what do you mean? Of course there’s a woman president, of course it’s no big deal, like it’s fine. And so I think that we all wanted to make sure that we got to that point.

MARTIN: You know, you have a chapter in the book — oh, here it is. How do I get to be you by the time I’m 35. And one of the points you make is don’t ask that question.


MARTIN: You just — it doesn’t really work that way.


MARTIN: But one of the other points that you make is that you can’t plan and micromanage every single step of the way.

MASTROMONACO: Yes. I think that one of the interesting things for me was that I, you know, was born in the ’70s, it was — when I went through middle school, high school, college, it was still much more like choose your own adventure in a way that was fine. I feel like things have gotten so competitive and people getting into schools, it just didn’t that way when I was growing up and as long as I was not in trouble, my parents were more than happy to sort of let me find may way. And being in the Senate, being in the White House, I encountered so many kids that were so programmed, that were so — you know, they’d get the chance to talk to someone like me and they didn’t ask about the experiences or the trips or what’s the most interesting thing or the saddest thing, they were like how do I get to be you. And I thought that was such a sad use of their time that I would stop them dead in their tracks and I’d say, if you wanted to be me, you — I could never have asked that question of anyone because I wouldn’t have ended up here. Because if I had asked that question years ago, would I have picked Barak Obama —

MARTIN: Barack Hussein Obama.

MASTROMONACO: — Hussein Obama, junior senator from Illinois or Hillary Clinton? Like who would have been more — I go, but the truth is I was with the man I believed in, who before he even decided to run for president looked at the 6 of us or 8 of us around the table and said, here’s the deal, I’m running as me, I’m going to win as me or I’m going to lose as me because I would rather lose as myself than win trying to be someone else. And we were like, great. And that sort of instilled in us this, you know, if we were on the high wire every day taking risks and if we messed up, he wasn’t mad as long as we were still out there taking risks and — and doing what we though was interesting and new. And so for the young people now, I’m like, if I had used your mentality, where would I have ended up? And they’re like but you got to be deputy chief of staff, I’m like, because I was with him from the beginning, he trusted me when I didn’t even think I was ready to be deputy chief of staff for operations. He was like, well you’re the only one who doesn’t think that, so stop.

MARTIN: It’s kind of the anti-lean in. You can’t sort of plot, you know, A to B to C. There is no way anybody would have —


MARTIN: — plotted my trajectory. Is that mainly for women? Is it just different for women?

MASTROMONACO: I think it’s different for women but I also think that if men sort of listen to some of the stories that they might lighten up a little bit and that it won’t just be so, I’m a man, here’s what I’ve been taught, here’s what I’m supposed to do. If we can all just sort of, like, loosen up a little bit and not thing about everything that’s happened before us and think about how we want to live our lives going forward, I think that’s good for everyone.

MARTIN: So how are you dealing with the present moment when the current occupants of the White House are very different people? How are you dealing with that?

MASTROMONACO: So, you know, the one thing about working in the White House that not all Democrats like me to say or like to hear from me is that, you know, the Bush administration could not have been more generous or kind to us, they could not have helped ease the transition more than they did. They were extraordinary. And you know, after we had been there for a year, we would always talk about that you really don’t understand until you’ve walked in the shoes. You know? Like yes, they’ve made a lot of mistakes but — but now we understand a bit more how those mistakes could have happened. And so I try to be — after the election in 2016 and Barack Obama came on television, you know, the day after and he said we support the new president-elect, you know — and I was like if he can do it, I can do it. And because I know how important the institution is. It’s not politics at that point, it’s governing. And you’re not president of the group that elected you, you’re the president of all the people. So I had hope. I was like, Donald Trump is going to ascend, he is going to blow our expectations, he’s going to understand the weight of the job.

MARTIN: And you still think that?

MASTROMONACO: No. No, no, not — not shortly after. You know, I tried to stay upbeat and positive but for me, the thing that upsets me — you know, the tweeting and all that garbage, that’s one thing. To me the thing that (inaudible) I know things that the Clinton administration, that the Bush administration, that we did, ways that opened up the government and the White House to all the people in the country, that made it feel accessible, that — that really understood the importance of the ceremonial parts of the job. And so the thing that makes me the saddest are all of those kids and all of those Americans who like aren’t going, who aren’t seeing the respect. You know, when you walked into the Obama White House, when we walked into the Bush White House, I mean, it was — it was so serious and so aspirational at the same time. And I think that when you have people who so openly attack public servants, who have given their lives to their country, to me that’s something that I hope we can bounce back from.

MARTIN: You have a chapter in the book about Monica Lewinsky —


MARTIN: And you say that, you know, she hasn’t — how can we say? She hasn’t gotten her due, that she has not really been given the respect that she deserves. Do you want to talk a little bit more about that?

MASTROMONACO: Well I think it’s happening. Part of what I wanted to talk about was that even though she and I were the same age, roughly, when she went through what she went through, becoming a public – like one of the most recognized people in the world at the age of 24 that there are interesting things that we need to take from that which are back when I was sitting on my living room floor with my roommates walking the impeachment trial on a black and white television, we got our news from Dan Rather, Tom Brokaw, Ted Koppel, Peter Jennings, right? It never occurred to me that the story being told by four white men would be different if there was a women telling the story when we sat down every night at 6 o’clock to watch the news. So on the one hand we were getting sort of straight facts, right? And I think now we wish we could get more of a coalition around what straight facts are. But what’s important is the point of view, and the point of view that was missing back then was Monica’s point of view. And if you asked people to think back on, you know, 1998, 2000 and you ask them who the victim was if you were a democrat, they’d say Bill Clinton. Wow. Like the thought that people didn’t see her as a victim of power, of a man in power, of the media. And so, for me when I became friends with Monica and part of why I wanted to write this essay is because we all have to think about things from the other person’s point of view, and I wish that I had been more aware and more curious back then and thought more about what she might have been going through. And so, now I think that I try to do that in as much as I can with other people.

MARTIN: And yet, it just seems as though the way our kind of fresh look occurs is still within the context of a polarized experience. I mean, I’m thinking about –


MARTIN: – Brett Kavanaugh confirmation hearings and that Dr. Christine Blasey-Ford had information that she wanted to have considered –


MARTIN: – and yet it still seems as though the information can’t be considered on it’s own merits.


MARTIN: It still has to be filtered through the prism of a polarized political perspective.

MASTROMONACO: Right, and the thing that I felt at least this time around is that Dr. Blasey-Ford knew she wasn’t alone. If it taught us nothing it’s that we couldn’t be silent, that people did take to the streets. I can’t tell you how many like rallies I spoke at just so that we could say we see you and we hear you and you’re not alone. And so, that’s definitely not the third way, but I do think that there’s a, you know, #neverforget for the things that have happened before where we look back on the impeachment hearings, we look back on Anita Hill, we look back on Anita Hill standing in front of a – sitting in front of dayas of white men and trying to impugn her character. And so, change is not happening as fast as it should, but there is – it is heartening, I guess, to see that at least we have found a way to pull together and tell these women when they come out that they’re not alone.

MARTIN: There is unprecedented number of women running –


MARTIN: – for president. There’s –

MASTROMONACO: Six now, right?

MARTIN: Six now, right. And there’s also a record number of women in Congress and I just wonder if you think that’s going to change things?

MASTROMONACO: I do think that’s going to change things. Now, how long have we been hearing when – this is such a tongue twister – when women run, women win, and I think that we’ve all been like, OK, sure because OK. But now they actually all did run and so many of them did win. And so, I do think that it’s going to change governing going forward if only because now the more that women run I think the more – I mean, who ever thought that Joe Crowley would lose a primary to Alexandria Ocasio-Cortez? Like – so I think that, one, people are going to take their positions in power more seriously, and when you think about how dismissive some people are when they have a primary opponent who could potentially 28 and a woman, you know, they’re going to take it more seriously now, and there’s nothing but good that comes from that.

MARTIN: So it’s interesting that of the class of new –

MASTROMONACO: Members, yes.

MARTIN: – newly elected members, the people who have become lighting rods are all women and I wonder why you think that is?

MASTROMONACO: Of course. Well, I think that they’re the ones really putting themselves out there. Like I think that in a lot of ways Alexandria Ocasio-Cortez only wants to be in Congress if she’s going to do and fight for exactly what she believes in. If that means she’s a lighting rod, so be it. And also there’s strength in the women that came in together. And so, you’re not going to push that hard and then get into Congress and sit there with your legs crossed and your hands on your lap and just do what people tell you.

MARTIN: Well there it is.

MASTROMONACO: There it is in a nutshell.

MARTIN: In a nutshell. Alyssa Mastromonaco, thanks so much for talking to us.

MASTROMONACO: Thank you for having me. This is a real honor.

About This Episode EXPAND

Christiane Amanpour speaks with Walter Dellinger and Jeffrey Toobin about the Mueller report; and filmmakers Abigail Disney and Eimhear O’Neill about the series “Women, War & Peace.” Michel Martin speaks with former White House Chief of Staff Alyssa Mastromonaco about her new memoir.