An Insignificant Hustler Yearns To Be A Big-Time Operator In The Ironic 'Norman'

TERRY GROSS, HOST: This is FRESH AIR. I'm Terry Gross. My guest was part of President Obama's inner circle at the White House, but she is not famous. In fact, in 2011, she was included on the New Republic's list of "Washington's Most Powerful, Least Famous People." But now her name, Alyssa Mastromonaco, is becoming a little better-known with the publication of her new memoir, which is a bestseller. It's called "Who Thought This Was A Good idea?"

It's not an expose, it's about what it takes to make things work at the White House and how stressful the process is. Mastromonaco was assistant to the president and director of scheduling and advance at the White House from 2009 to 2011, then served as assistant to the president and deputy chief of staff for operations at the White House from 2011 to 2014. She started working for Obama in 2005 when he was in the Illinois Senate and running for U.S. Senate. Before that, she worked for John Kerry and served as his director of scheduling during the 2004 presidential campaign. She's now an executive at A&E Networks and a contributing editor at Marie Claire.

Alyssa Mastromonaco, welcome to FRESH AIR. Let's start with what your job descriptions were as chief of staff for operations and then the position that you held before that.

ALYSSA MASTROMONACO: Well, as deputy chief for operations, I oversaw everything from the research, selection, nomination, interview process and confirmation process for Cabinet secretaries and political appointees across the administration. I oversaw the White House Military Office, which is about 3,000 mostly military members that ran Camp David, oversaw the maintenance and operation of Air Force One and Marine One, the scheduling and advance operation, which I had previously run before becoming deputy chief, which oversees the president's daily schedule, his long-term schedule, foreign travel, negotiates with foreign governments when we're traveling abroad and basically anything involving the first family and the Secret Service.

GROSS: Whoa (laughter). That's is some job description. And before that, you were doing scheduling and advance for President Obama.

MASTROMONACO: That's correct. I was the director of scheduling and advance on the 2008 campaign and then for the first two years in the White House.

GROSS: OK, so by this point in President Obama's presidency, and I just read this in The New York Times, President Obama had made public appearances in nine states, took three overseas trips and was beginning his fourth journey abroad. And you were organizing all of that?

MASTROMONACO: We were.

GROSS: So what stands out from that first less than a hundred days of President Obama's presidency in terms of your job?

MASTROMONACO: So I think for me, you know, on the campaign, you get used to a certain rhythm. You work with the same people. And this was a total re-acclamation. You have far fewer resources than you would actually imagine. One thing people don't know is that the president's travel budget is not unlimited. And when we would travel to those nine states for official events, you actually have to work with all of the Cabinet secretaries to figure out who is going to sponsor the trip.

So is the trip about agriculture? Is it about education? So that was actually something that we never expected that was quite hard because you basically become an internal fundraiser with the agencies. And planning the foreign trips, you know, we took the lead, basically, from folks at the State Department who had been there for many years and knew how to execute a flawless trip. They taught us what we needed to know. And we sort of also followed the lead of the White House military aid to the president. Everybody knows that's the person who carries the football.

But they also transition, you know, their rotations transition from administration to administration. So one of our first MIL aides that helped us was actually had been with President Bush for a long time. So one of the things that I think about when I see President Trump and his administration is that I hope that they are taking the time to learn the lessons that we did. It's a very humbling experience, those first hundred days. Everything that you think you know is sort of turned on its head.

So for us, we were running pretty fast those first hundred days. But we laugh because when we look back, the first day the president was in the Oval, that whole day before when we were trying to prepare his day, you would have thought that we were sending him into a war zone we were sweating so hard. When really when we look back on that schedule, it was three meetings, two of which were in the Situation Room. So it is a very different beast.

GROSS: So when you look at President Trump's travel schedule, which, you know, he's been to several states, no trips overseas, but is constantly going back on weekends to Mar-a-Lago, you said the travel budget for the president is not unlimited. So what do you think his travel budget is like now? What do you think traveling back and forth to Mar-a-Lago most weeks is costing?

MASTROMONACO: So what I actually read last week, which was very shocking, is that currently, President Trump is on track to spend in one year what the Obamas spent in eight years on personal travel.

GROSS: So is personal travel a separate expense line in the budget?

MASTROMONACO: Yes. Personal travel, there is not an actual budget for personal travel, you just try to keep it as low as you can. You know, President Bush would go home to Crawford. And that was pretty standard. They had a real way of operating. But one thing that people forget when they try to compare the Trump trips to the Bush trips is that every president gets a secondary residence. So they live in the White House, but for the Obamas, it was Chicago.

And for President Bush, it was Crawford. And for President Trump, it's actually New York City, which is why those trips to Florida are so expensive. Because when President Obama or President Bush went to their homes, their infrastructure to protect them and support them was there and it stayed there, so it wasn't a constant expense. So, you know, President Trump is someone who criticized President Obama for driving down the street to Andrews Air Force Base to play golf on the weekends.

I just - I would love to know how he justifies this as somewhat different.

GROSS: So when President Obama came to the White House and you came with him, you were working on events. And you said, you know, and you had to, like, create and schedule events, that the Secret Service was especially unwilling to do anything remotely risky because President Obama was the first African-American president. Can you talk about some of the things surrounding that, surrounding what I imagine is all the threats against him?

Because in addition to it being, like, an incredibly divisive atmosphere as the first African-American president, there was so much racism that was being directed at him overtly or covertly. So how did that affect his ability to do events and what it took to schedule, you know, events for him?

MASTROMONACO: So a couple of things. A lot of people, of course, compared us to President Clinton and how President Clinton got out more and he did these sort of sweeping, beautiful events on the, like, at the Grand Canyon when he would sign bills. And what people didn't realize is not only, you know, was Barack Obama the first African-American president, he was a post-9/11 president, which is a totally different beast. And also, it was the first presidency that was completely within the age of social media.

So when people talk about the uptick of threats that the Secret Service would report, so much of that was because of the advent of Facebook and Twitter. It was easier to make the threats for people to count, right? And so when we were first getting started, none of us wanted to ever put anyone, you know, at unnecessary risk. I don't think anybody would want to do that. But for us, there were a lot of grand ideas that people had. One of them was having him do an event on the Triborough Bridge. And I knew that there was no way on earth that the Secret Service was going to allow that.

But I think even now with President Trump, they wouldn't allow that because it's just such a different world. Technology is so different. You can detonate a bomb with a cell phone. We know that now. And so it's different. Even on the rope line with President Obama, when people would hold up their iPads or their iPhones to take a picture, Secret Service always asked them to put it down because they can be, you know, a device.

GROSS: So since you had so much of a role in finding and selecting people for Cabinet positions and other positions, what are some of your reflections watching the selection process for President Trump's cabinet?

MASTROMONACO: Well, you know, I look at it and I just remember how much thought and vetting went into the folks that we were selecting. And I think that there was one moment that struck me when he was talking about nominating Steve Mnuchin to Treasury Secretary and how he should be given the same speedy confirmation that Tim Geithner was. And people may recall that Tim Geithner was the chair of the New York Federal Reserve, which I think is a much more translatable skill set, let's say, than having been an executive at Goldman Sachs.

And so I think that's, you know - the president didn't seek out - President Obama rather - didn't seek out people who singularly agreed with him. He did go for sort of a team of rivals or, you know, differing perspectives and thoughts because he wanted to be the president of all of the citizens of the United States of America, not just the Democrats. And so, one, I think that the Trump folks - I mean, we moved deliberately, but we moved quickly. And so many agencies right now are home alone, no deputy secretaries, things that cannot be blamed on Congress because they haven't even nominated people - no deputy secretary of state, you know, no people at the State Department at all practically.

So I would hope that they would focus a little bit more on what it takes to make the government work and then criticize the government for being slow. But right now, I don't think that they have a fair, accurate representation of what the government actually does because there's no one there to do the work.

GROSS: Can you translate for us practically what it means to not have a deputy secretary of state and to have a lot of positions open in the State Department?

MASTROMONACO: Sure. So one thing - like, for example, something that people have not talked about that much, but during the Obama administration, the State Department did daily press briefings. And those briefings were the way that foreign service officers all around the world got their information. Well, those haven't been happening.

So foreign service officers are being sort of cut out of the loop in the countries where they work because people know they don't have information. Having a deputy secretary of state, you know - if you look at Secretary Clinton or Secretary Kerry, they travel all the time. So the two deputy secretaries really help run the agencies whether it's for policy - like the policy process or, you know, resources and management.

And so to not have anybody doing that, then all the people below have no guidance and those positions haven't been filled. And there is a distrust, you know, that isn't something I'm making up. It's something that the Trump folks have stated, this mistrust for the career employees who are actually the people that carry us from administration to administration with depth of knowledge and institutional knowledge. And so I can't imagine - for example, if President Obama were having a meeting in the Situation Room on Iraq, there would be a process at DOD, at, you know, DOJ, at the State Department that went down into all the various levels of expertise so that what was ultimately served up in the Situation Room was a deep and considered process - like a product of a process.

And it wasn't, you know, this haphazard let's make things happen fast, but not really understand the consequences of our actions. And President Obama always wanted to know cause and effect, right? And so you can't really know cause and effect if you don't have all of the facts.

GROSS: If you're just joining us, my guest is Alyssa Mastromonaco, and her new memoir about serving as President Obama's deputy chief of staff is called "Who Thought This Was A Good Idea?" We're going to take a short break and then we'll be back. This is FRESH AIR.

(SOUNDBITE OF JEFF COFFIN AND THE MU'TET'S "LOW HANGING FRUIT")

GROSS: This is FRESH AIR, and if you're just joining us my guest is Alyssa Mastromonaco. Her new memoir "Who Thought This Was A Good Idea?" is about working for President Obama as director of scheduling and advance at the White House from 2009 to 2011 and then as assistant to the president and deputy chief of staff for operations in the White House from 2011 to 2014. She's now an executive at A & E networks and a contributing editor at Marie Claire.

So another thing that you had to do as deputy chief of staff is work with agencies like the Department of Defense to run classified construction projects and maintain the continuity of government exercises, exercises so that if theres a nuclear attack or if Washington floods or the president is incapacitated, everyone knows what to do.

MASTROMONACO: Exactly.

GROSS: Just mentally, emotionally, what was it like for you to be in charge of planning for the absolute worst?

MASTROMONACO: Oddly, it was actually very reassuring when you sit down with the folks who, again, from administration to administration keep this process alive and have this information. You know, you sit down, and they brief you. And you're like, oh, wow, if something happens, actually everybody does know what to do. And so I found it - on the one hand, it's very heady. You're like I can't believe that I'm seeing what would happen if a nuclear missile was launched from X and how long it would take to get here and what happens.

But it is comforting to see that these processes are pretty well socialized. Everybody knows them. You know, the 25th Amendment has been one of the funnier things that happens is you obviously notify the speaker of the House and the majority leader, minority leaders in Congress. And we realized that the - when we actually ran the exercise that all of the fax numbers were wrong because people didn't really use faxes anymore. So that was - we're like, oh, we should get new fax numbers. And you sort of do what's called validating the exercise every couple of years if you haven't used it in real time. You sit down, and you do what's called an exercise. And you run through all the steps to make sure nothing's changed, the fax numbers are still there and that the documents are still valid and don't need to be updated.

GROSS: Can you tell us what your role was supposed to be in case of the worst, like, where you would be and what your job would be?

MASTROMONACO: If - I can't really talk about what my job would be - but in both - in a scenario of the president being incapacitated, say, he needed to have surgery, I sort of ran the process, the many steps of the 25th Amendment and sort of bringing that to life. And then the - in, like, worst case scenario, if the president had to go some place, I would have been part of the crew that was evacuated with him.

GROSS: What was the closest you got to having to enact one of those plans?

MASTROMONACO: Goodness. Oh, I would say it was when the president had his colonoscopy.

GROSS: Wow. If that was the worst (laughter).

MASTROMONACO: Knock wood. Yes, that is the worst I remember.

GROSS: So you were preparing for, like, say it really doesn't go well...

MASTROMONACO: Yes.

GROSS: ...Or just for that period when he's incapacitated...

MASTROMONACO: Just that period when he's...

GROSS: ...Because he's under a light sedative.

MASTROMONACO: Exactly. And we figured this is a great time for us to, you know, go through all of the steps, and it was a - it was an interesting exercise.

GROSS: Right. OK.

MASTROMONACO: You feel very - you feel like you're in the, you know, "The West Wing" television show in those kind of - in those scenarios.

GROSS: So what did you have to do to get the president in and out of Iraq or Afghanistan which were, you know, war zones? And what is the secret service and weaponry like when you fly with the president into a war zone?

MASTROMONACO: You know, it's - there's a lot of it. You know, you have the counterassault team, of course. And usually when you're working with, you know, President Karzai's team they're pretty - I mean, nobody wants anything to happen to the president when he's coming to take a visit because that reflects so poorly. I mean, President Karzai wants people to believe that, you know, Afghanistan is not that dangerous. And so, you know, having anything bad happen to the president of the United States when he's there would be quite bad. So they were usually pretty helpful. I mean, not always as helpful to me because I was a woman, and so sometimes they would make me sit out in the courtyard when all the guys went inside.

But the Secret Service - and they were always quite protective of me. Like, they understood that in a lot of these places people were a bit hostile towards me. But no, I mean, Secret Service acted - of course it's heightened, you know, when you're going someplace that is - that can be that volatile. But for the most part their standard was always - they were always at a 10 out of 10 on the preparedness scale.

GROSS: Tell me more about having to sit out in the courtyard because you were a woman.

MASTROMONACO: So one of the - I think it was the first time that I was at President Karzai's palace, which is so interesting because you arrive at night. And when you're sitting in the courtyard - I don't know what it was about it. It might have been sort of the vegetation. But it feels very European. It almost feels like the Alps. And so I was walking in with the president and the guards just closed the door. And I tried to get in. And of course, everyone else is following the president, and he walks in and goes upstairs to his meeting with Karzai. So it's not like he's sitting in this room looking out and it's, like, my face is pressed against the window or anything.

But when he came down he realized that no one had seen me. And so Robert Gibbs, who was White House press secretary at the time, he tried to come out and get me. And I was like, Robert, it's fine. Just leave me out here. And so I just - I sat in the courtyard. And at the time I think I smoked a cigarette because what else do you do? And - but Karzai's folks did actually bring me some rice and some goat, which was quite tasty.

GROSS: Is this the kind of thing that happened to you a lot when you were traveling abroad to Muslim countries where you were shut out in some way?

MASTROMONACO: You know, not really, to be honest. When we went to - I'm trying to think. Most places were quite open. They know that you are an American and that you're a diplomat in this capacity. And so they're quite generous and sort of fluid, I guess, in these situations. And one person had told us when we went to - it was customary for King Abdullah of Saudi Arabia to not shake women's hands. And that when you got off the plane and went through the receiving line that you basically should keep your hands down by your sides and just say nice to meet you and keep going.

And so you line up in precedence order, right? So it's like, you know, the chief of staff would be first, you know, followed by the senior advisers and then me and the national security adviser. So when we were getting off the plane in Saudi Arabia, Valerie Jarrett and I, who traveled together a lot, she and I knew, like, keep your hands down and just keep going. But King Abdullah put his hand out to us. And I was petrified. It's like I didn't want to cause an international incident and shake his hand when I wasn't supposed to. But he had his hand out, and President Obama was standing there and he's like, shake his hand.

GROSS: (Laughter).

MASTROMONACO: So we did. And it was - and so for that - you know, mostly it was just that there weren't a lot of women in general around, not that they didn't really let us be there. Like, we were always welcome. There were - we were just usually - Valerie and I were among the only two women sometimes in lunches of 30 people.

GROSS: My guest is Alyssa Mastromonaco, President Obama's former deputy chief of staff for operations at the White House and author of the new memoir, "Who Thought This Was A Good Idea?" After a break, she'll tell us about the fiasco she nearly created. I'm Terry Gross and this is FRESH AIR.

(SOUNDBITE OF TED NASH'S "WATER IN CUPPED HANDS")

GROSS: This is FRESH AIR. I'm Terry Gross back with Alyssa Mastromonaco, who's written a new memoir about working for President Obama called "Who Thought This Was A Good Idea?" She started working with Obama when he was campaigning for the U.S. Senate. After his presidential victory, she became assistant to the president and director of scheduling and advance at the White House. From 2011 to 2014, she was deputy chief of staff for operations at the White House. She frequently traveled with President Obama.

So tell us about Air Force One.

MASTROMONACO: Air Force One. Air Force One and the White House medical office are the two things that you miss the most when you leave. People talk about, oh, it must be so not - you know, oh, Alyssa, like, Uptown problems, you always flew on Air Force One. I said, yeah, but now I have no frequent flyer miles anywhere so I don't get upgraded.

GROSS: (Laughter).

MASTROMONACO: So it's doubly hard. But no, it is - I will tell you that - and it's one of these things that when I when the Trump folks, I just don't know if they feel the same way that we did. But getting on Air Force One for the first time was the most humbling, awe inspiring - you know, you were trying to be an adult - right? - but you're literally a kid in a candy shop. You're like can I take a tour? Can I go up and see where all the equipment is? It is a lot like you see on TV.

But the best part of - well, and what people don't totally know, they're like, oh, you know, we would fly President Obama, like, to be very efficient with his time. So many, many trips, we would leave Washington at night, fly overnight and then land in country the next morning around 8 o'clock and start our day. And people wouldn't understand there aren't like beds for us on Air Force One. We have those like Snuggies that you buy on QVC. And we would sleep on the floor. And the best part of becoming deputy chief, especially when Valerie Jarrett didn't travel, is that I could claim the couch. There was one couch that you could sleep on. And then you'd get up. And everybody shares one - two bathrooms.

So you get up, everyone's brushing their teeth, washing their face. And there's a line for the bathroom. And Valerie and I were always quick to be the first two to wake up so that we would sort of have the bathroom in a fresh state. And then you get ready and you have your breakfast. And you go down and you start your day.

And there is nothing like walking off the steps of Air Force One. It is - you - every single time, you never don't feel proud. You always feel so proud. And I think that we were just always - the reception too of other people in countries when they see that beautiful, like, blue and white plane, it's just - it always gives you goose bumps.

GROSS: You had to sleep on the floor?

MASTROMONACO: Yeah. We would sleep on the floor. The seats didn't recline all the way, so they could be really uncomfortable. And so we would - a lot of us would sleep on the floor.

GROSS: Wow.

MASTROMONACO: See, it's not that glamorous.

GROSS: No, really. So - and now you had to fly coach? (Laughter).

MASTROMONACO: I do.

GROSS: (Laughter) What a comedown.

MASTROMONACO: It's a real bummer when you're in, like, boarding group D.

GROSS: (Laughter) So what was the worst fiasco that you were involved with? This is assuming there was a fiasco.

MASTROMONACO: Well, this was sort of funny. It wasn't quite a fiasco but there was this period of time - I think it was in 2011 - when that Icelandic volcano erupted and caused that plume that sort of circled the globe and was quite dangerous for planes because if you flew through the plume, it would melt the engines and the plane would crash. And so we had several trips at that time that were scheduled, foreign trips.

One was - you'll recall I think it was the president of Poland was killed in a plane crash. And the funeral was happening and we couldn't go because of the plume. But then a couple of weeks later, we had to go to Asia. And we were in - I think we were in Indonesia. And we were at a summit. And I got a report from the military aid that the plume was coming dangerously close, and that if we didn't take off in like the next two hours, we were going to be stuck in Jakarta. And so I got on the phone with the millaid (ph) - an Air Force - the captain for Air Force One.

And as president - when the first time President Obama met Colonel Turner, he said that's exactly what I want my pilot to look like 'cause he looked like a total bad ass with his buzzed hair and he was really tough. But I found Colonel Turner. I said, you know, what are we going to do? We have to get out of here. We can't be stuck in Jakarta. And he said, well, the best thing for us to do is be number one in line for takeoff. And he said but the Chinese are pulling their plane - they're taxing the plane out.

And so I sort of had to make this decision. And I told him to cut the Chinese off and pull out Air Force One and get us first in line for takeoff. And we had to hurry to the plane. And the president was like - and all of the military folks on the plane were like, oh, this is great, we're taking off. You know, we could have been stuck here for three days, and the president's like, well, what do you mean?

They're like, well, if we hadn't been the first in line to take off, we would probably be stuck. We couldn't get back to the U.S. And he said, well, how did we get first in line for takeoff? And they said Alyssa told us to cut off the Chinese. And he looked at me like I could potentially have done something very bad but at the same time was very glad because we all wanted to go home.

GROSS: This could have started a conflict with the Chinese (laughter) because of American arrogance.

MASTROMONACO: It could have, but like - exactly. But it worked out OK. We got home plume-free. But that plume wreaked havoc for months.

GROSS: Well, it's a huge responsibility to, you know...

MASTROMONACO: Yes.

GROSS: ...You can't be flying with the president if it's dangerous and the plane might go down, right? I mean, that...

MASTROMONACO: That would really be bad.

GROSS: ...Would be bad. (Laughter) Yeah, that would be bad.

MASTROMONACO: That would really be bad because as he would remind us, if that ever happened, it would be President Barack Obama and several unnamed staffers.

GROSS: (Laughter).

MASTROMONACO: We were like we know, we know.

GROSS: So one of your legacies - I underscore the importance of this, you know where I'm going (laughter).

MASTROMONACO: I know. Go there.

GROSS: I'm going. You had a tampon machine installed in one of the ladies rooms. And apparently there aren't many of them in the White House.

MASTROMONACO: Yes. The White House, the West Wing, does not have as many bathrooms as I think any of us would have hoped. And the women's bathroom downstairs, which was near my first office, I think it was three stalls. And all you ever wanted was a tampon. And there just weren't any. And so we would all have - all of the ladies sort of had a code that was like, you know, the tampons are in the upper right drawer of my desk, help yourself. But sometimes everybody would be out. And then inevitably, it was on someone's assistant - usually mine, both of them were men - to go to CVS, which is sort of a pain to go to in the middle of the day, and pick something up.

And so when I became deputy chief, I was in the bathroom one day in desperate need and didn't have one. And one of the people who reported to me, Katie Keel (ph), was the assistant to the president for office and administration. She oversaw all of the White House personnel and the campus. And I said Katie, is there any reason we can't have a tampon machine in the West, you know, ground floor bathroom? And she said I don't think so.

And so she went. Two weeks later, we had one. And one, it's great that we were able to do that. But the real point of the story is that you should always ask for - I think for years and years, people assumed there was some reason it couldn't be there and it just took me asking to make it happen. It's not like - I wasn't really breaking ground there. I think I just asked a question.

GROSS: Is there like an engraved placard next to it?

MASTROMONACO: No, there isn't which is why I felt a need to write about it so I could hog all the credit in my book.

GROSS: (Laughter) Right. Let's take a short break here and then we'll talk some more. If you're just joining us, my guest is Alyssa Mastromonaco. And her new memoir is called "Who Thought This Was A Good Idea?" We'll be right back. This is FRESH AIR.

(SOUNDBITE OF CAKE SONG, "TOUGHER THAN IT IS")

GROSS: This is FRESH AIR. And if you're just joining us, my guest is Alyssa Mastromonaco. Her new memoir, "Who Thought This Was A Good Idea?" is about working for President Obama as director of scheduling and advance at the White House and then as assistant to the president and deputy chief of staff of operations at the White House. She's now an executive at A+E and a contributing editor at Marie Claire.

The New York Times reported that you played a lead role in the selection process of Joe Biden as Obama's running mate. Is that...

MASTROMONACO: Yep.

GROSS: So what did that mean? What did you do?

MASTROMONACO: So for both Senator Kerry and then for Senator Obama, I was sort of the, you know, there was the team that led the vetting process and did the binders on each person that they reviewed with the president. And then for both Senator Kerry and Senator Obama, I - once they had narrowed it down to, say, three or four people, they would hand over contact information to me. And I would set up private meetings between Senator Kerry and whoever the candidates were or Senator Obama and the candidates. And then at one point on the Obama campaign, I got David Axelrod and David Plouffe around to meet two or three people as well.

And the whole point is just making sure nobody sees them. And this came from - it didn't - it wasn't always this way. And as we saw this time how Trump did it, I mean, he sort of rolled everybody out and did events with them and sort of let it be known that they were being considered. But back in 2000 when I was working for Senator Kerry, he had been on Vice President Gore's short list. And it had sort of been put out there that he was the leading contender. And then it ended up being Joe Lieberman. And it was a very embarrassing sort of process, you know, to - for - to be John Kerry and have been put out there and then sort of, you know, have to hide in the house while the press are sort - staked out on your sidewalk.

And so when Senator Kerry ran for president, he wanted a process that was super respectful, super clandestine, didn't want anybody's name out there because he didn't know who he was going to pick. And he didn't want anybody looking like a runner-up. And then Senator Obama, when he decided to run, he liked John Kerry's process so much and thought it was so respectful that he wanted the same thing. And lucky, I worked for him too, so I did it again.

GROSS: Must have been interesting for you to watch the reality show at Trump Tower when the potential nominees were coming to meet with Donald Trump.

MASTROMONACO: I mean, it was an absolute beauty contest. People come in and they wave and they go up. I couldn't believe it. I mean, at one point when I was with John Kerry, there was one reporter - we were in a building and he had met with Bob Graham. And there was one reporter - one reporter - who was coming down the ramp in the parking garage.

And I pushed Senator Graham into the car and threw his jacket over his head so no one would see it was him. I mean, that was how we did it. We certainly didn't, you know, put up a step and repeat banner like the Vanity Fair Oscar party and have people take a picture.

GROSS: Does work at the White House stop on weekends?

MASTROMONACO: No. No, no, no. You know, of course having - you know, we had BlackBerrys back then. But we usually, at least a couple times a month, had a scheduled Saturday sort of planning meeting. And it was very casual. You could come in in jeans or, you know, workout clothes. And we would sit down and go over things. But you always had to be available. And I, when I became deputy chief of staff, got a secure communications system that was in my bedroom, made it quite warm because there's an actual server next to your bed. And my apartment was not that big.

But you could always be reached. Sometimes, you know, 3 o'clock in the morning the red phone rings and it's the Situation Room and something's happened. And they would call me and say, you know, should we alert the chief of staff next or should we go straight to the president? And I would say, you know, go straight to the president, you know, or simultaneous, you know, notify them simultaneously. But no, I could never say that I was off ever.

GROSS: So I thought this was really interesting. You had to get national security clearance for your job.

MASTROMONACO: Yep.

GROSS: One of the questions you had to answer was a kind of detailed list of your drug use. And you'd smoked marijuana.

MASTROMONACO: Yes.

GROSS: You had to say how many times (laughter).

MASTROMONACO: Yes. That was...

GROSS: Yeah. So you handled it by saying unknown. How did you come to the conclusion that that would be your answer - an unknown number of times?

MASTROMONACO: Because - well, because I really feel strongly about not lying. And so when the FBI agent asked me for a number of times and she said, you know, 20? And I was like no. She said, a hundred? I said no. And then when she got up to 500, I was like I'm not saying - I'm not giving you a number because who knows if they're going to go try and prove the number. So I just said unknown. And apparently from her reaction, nobody had ever said that before.

GROSS: You write that you had to get randomly drug tested almost every month. Is that because you'd said unknown or does everybody have to do that?

MASTROMONACO: No. Most people get drug tested like once or twice I think that first year. But I was drug tested quite often because I was very forward-leaning about my drug use, very open kimono as we would say. And so yeah, every - just about every month you'd get an email that said, you know, you have 24 hours to show up for your test. And I would. And it was fine because I wasn't. So I had nothing to hide (laughter).

GROSS: You made a point of not smoking while you were working at the White House.

MASTROMONACO: Oh, yes. No, no, no. I was - I dodged a bullet. I was glad I was able to get my job. And so I certainly wasn't going to jeopardize it.

GROSS: OK. So you were under a lot of stress in your position at the White House. Most people at work you can always say to yourself, well, it's just a radio show or it's just a whatever. You can't say, well, it's just the security of the United States of America, it's just the president of the United States.

MASTROMONACO: Correct.

GROSS: I mean, everything is at stake here. So talk a little bit about the level of stress and how you tried to deal with it.

MASTROMONACO: So the stress, there are two things. You know, you can manage the stress until - 'cause you - there's so much adrenaline. You know, I think I basically ran on adrenaline almost for six years. But eventually it all starts catching up with you, right? Like you can sort of - you can manage the stress. I think we were all pretty good at it. But it's that you never have sort of a down cycle to recover. And so if you - if I was planning a foreign trip - and a lot of times when you'd be planning a foreign trip, you're working on a completely different time zone for at least a week before you leave. And then you come back, and there's no vacation. There's no days off. You know, you're back in the office the next day. And so ultimately, I think it was the sleep that caught up and maybe had me not deal with the stress as well as I could have.

But by about the end of 2012, I had - I was in my office with David Plouffe, and I was typing while I was talking to him 'cause I can do that. And he said, Alyssa, what are you doing? And I'm like, what do you mean? He's like, none of the words on your computer screen are words. And I looked and it was just, like, gibberish, basically. And I realized that I wasn't quite right, that something was off. I thought about it. I had been forgetting things a lot lately.

Like, not big things but the things that are easy, like I'm in the car halfway to work and I couldn't remember if I had fed my cat. And it turned out, they give me a gross neurological exam, that I was basically functioning sort of on, like, 50 percent of my capacity and that I was very sleep deprived. And so that was actually when they said, look, you know, you've got to start going to bed at 10. You've got to take an Ambien. You have to get some real sleep.

You know, not just be in bed, but, like, go to sleep. And after about three weeks, I took the test again and I was up to, like, 85 percent. And so I was much, you know, I was on the right track. But it was a sign that, you know, I was probably coming to the end of my time and that I was so lucky to have had such incredible experiences. But, you know, maybe it was time for someone with fresh legs to take over and have the same experiences that I did. And I just - for all of the things that I would pride myself on - I normally have a good attitude, I'm sort of decent fun enough to be around. And I prided myself on being creative and being an idea machine.

And, you know, my ideas just weren't - they weren't flowing. I was becoming the person who sat at the table and when someone had an idea, I'd be the one who said, we did that, it didn't work. We did that in 2011. It was, like, I had too much memory. I'd been there too long. And so I decided that it was time for me to go because I wanted to leave on a high note. I never wanted to be that person that people are secretly meeting about about how to get them to realize their time has come so that they go.

And so I was glad to sort of decide on my own terms that it was time to go. And it was a really nice send off. And, yeah - and the president, you know, he's lovely. The best way to leave is to have your replacement in line. And I knew that I thought that Anita Decker Breckenridge, who I'd known for many years and who had worked for Obama for many years, would be a great replacement. And so it was a pretty smooth transition.

GROSS: OK. It's been great to talk with you. Thank you so much.

MASTROMONACO: Thank you so much. I loved it.

GROSS: Alyssa Mastromonaco is President Obama's former deputy chief of staff for operations at the White House and author of the new book "Who Thought This Was A Good Idea?" After we take a short break, critic at large John Powers will review the new film "Norman," starring Richard Gere, directed by Israeli filmmaker Joseph Cedar. This is FRESH AIR.

(SOUNDBITE OF DON STIERNBERG'S "PERDIDO")

TERRY GROSS, HOST:

This is FRESH AIR. The new film "Norman" was directed by Joseph Cedar, an Israeli filmmaker whose last two films, "Beaufort" and "Footnote," were both nominated for the Best Foreign Film Oscar. "Norman" is in English and is set mainly in New York. It stars Richard Gere as a Jewish small time operator hoping to hit it big. John says that "Norman" boasts the wit, feeling and storytelling precision that's largely vanished from today's movies.

JOHN POWERS, BYLINE: I once went to hear a philosophy lecture about the difference between being and doing. I can't remember the arguments, which were all about language, but I do remember the speaker asking this, if you do something good for bad reasons, are you being good or bad? It's a question you may find yourself asking during "Norman," the mordantly funny new drama by Joseph Cedar, the crack Israeli filmmaker whose previous film, "Footnote," was a brilliant comedy about the rivalry between father and son Talmudic scholars in Jerusalem.

Working for the first time in English, Cedar has created an ironic fable about an insignificant guy who yearns to be a player. When we first see Norman Oppenheimer, magnificently played by Richard Gere with tousled grey hair and a slight hunch, he seems like a successful businessman in his camel's hair coat. But we soon grasp that Norman's actually an operator, who, though basically well-meaning, is forever on the make. Prowling the streets of New York City, he tries to cobble together dodgy deals involving Israeli tax credits. And he traffics in personal connections he doesn't have.

He's annoying. And not surprisingly, the real power brokers flee him. But things change when he meets a bigwig who doesn't know him. That's Misha Eshel, a visiting Israeli deputy minister of trade, played with amusing panache by Lior Ashkenazi. Thrusting himself in Eshel's path, Norman tries to finagle them both into a dinner party at the home of a Jewish tycoon played by Josh Charles, then winds up buying the deputy minister a $1,000 pair of shoes, a purchase Norman can't afford.

Except three years later, Eshel becomes Israel's prime minister, and he remembers those shoes. After giving Norman a huge public embrace, Eshel declares him his personal go-to guy in New York City. Suddenly, the outsider is an insider. But because Norman can't stop boasting and scheming and promising, we sense he's destined for a terrible fall. Here, as the walls start to close in, Norman tries to wangle his nephew, played by Michael Sheen, into helping him get the prime minister's kid into Harvard.

(SOUNDBITE OF FILM, "NORMAN")

RICHARD GERE: (As Norman Oppenheimer) Thanks for coming down, really. I appreciate it.

(CROSSTALK)

MICHAEL SHEEN: (As Philip Cohen) You're acting like a maniac. Look at you. Why are you getting involved? This thing is bad for Israel, bad for America, bad for Jews, bad for everybody. Step away. Step away.

GERE: (As Norman Oppenheimer) You're right this is bad for everybody. That's why I want to help. That's why...

SHEEN: (As Philip Cohen) How can you help? This is a political war going on 7,000 miles from here. Eshel's rivals have found this cockamamie story, and they're going to use it to take him down. There is nothing you can do about it. Don't get involved. It's too big.

GERE: (As Norman Oppenheimer) Just this one thing, though, one thing. Just hypothetically, look, if this guy, this businessman, he comes to you for advice, he wants you to represent him, what are you going to tell him?

SHEEN: (As Philip Cohen) You want to approach him? That's a bad idea.

GERE: (As Norman Oppenheimer) No, no, no. I'm just thinking maybe we can come up with an option for him that's not so harmful to Eshel.

SHEEN: (As Philip Cohen) I'd throw him out of my office. That's what I'd do. I wouldn't want anything to do with him. He is a threat to a sitting prime minister. But even if it doesn't end up having any criminal implication, OK, apparently his dealings with Eshel are embarrassing enough so that his political rivals think they can use him to hurt Eshel. Eshel's people can't ignore that. They have too much to lose. They're going to strike back, and you want to avoid him like the plague.

POWERS: Cedar was born in New York. His family moved to Jerusalem when he was 6, and his film moves comfortably between New York's Jewish community and Israel's ruling class. Deftly sketching its elaborate skein of religious, financial and political relationships. It's an elaborate network of debts and favors, friendships and rivalries that connects everyone from Norman's rabbi, nicely played by Steve Buscemi in a bit of consciously witty goyish casting to an Israeli justice agent played by Charlotte Gainsbourg to a pushy street hustler played by Hank Azaria who is Norman's seedier alter ego.

Perhaps because Cedar is from Israel whose artists are less shy than Americans about tweaking Judaism and Israeli life, he tells Norman's story without worrying whether it's good for the Jews, to quote the classic phrase Sheen's character actually uses. Cedar cheerfully skewers Israeli politics and its emotional relationship to American Jewry in a way that U.S. directors dare not. And Micha Eshel - he offers up an Israeli leader whose friendliness can't mask his vanity, shallowness and self-promoting ruthlessness, nor does Cedar worry that Norman might play into anti-Semitic cliches.

This isn't simply because he is an actor as handsome and charming and gentile as Gere to play him. It's also because Cedar knows that if Norman is a type familiar in Jewish culture, this means he's a Jewish version of a human type. We all know someone like him. Business and politics are crawling with Normans, fantasists who puff themselves up, brag about knowing people they've barely met, offer to do favors they can't deliver and dream of a big score that never comes.

Far from mocking or hating Norman, Cedar clearly identifies with him. He gets us rooting for this lonely, desperate man who caught in surroundings that visually feel claustrophobic, spends his life trying to keep from falling off a treadmill that his own actions make go faster and faster. Early on, Norman flags down a jogging acquaintance in hopes of meeting his ultra rich boss. As the guy tries to brush him off, Norman tells him good things come in surprising ways. It turns out that he's right. "Norman" builds to a dazzlingly regulatory ending, one that's as elegantly constructed as its hero's life is messy.

GROSS: John Powers is film and TV critic for Vogue and vogue.com. He reviewed the new film "Norman." Tomorrow on FRESH AIR, how and why dictionaries define crude or offensive words like F-bomb and the N-word. Our guests will be Kory Stamper an associate editor at Merriam-Webster. We'll also talk about adding new words.

KORY STAMPER: I added bodice-ripper to the dictionary.

GROSS: Oh, really?

STAMPER: That's one I added (laughter).

GROSS: Stamper writers about her work as a lexicographer in her new book "Word By Word: The Secret Life Of Dictionaries." I hope you'll join us.

FRESH AIR's executive producer is Danny Miller. Our interviews and reviews are produced and edited by Amy Salit, Phyllis Myers, Ann Marie Baldonado, Sam Briger, Lauren Krenzel, Heidi Saman, Therese Madden, Mooj Zadie and Thea Chaloner. I'm Terry Gross.

Transcripts are created on a rush deadline, and accuracy and availability may vary. This text may not be in its final form and may be updated or revised in the future. Please be aware that the authoritative record of Fresh Air interviews and reviews are the audio recordings of each segment.