Tough times, your metal is really tested and i think i proved to him that his success was my number one priority, that his hard work on my behalf wasnt selfinterested and i had good judgment. Charlie judgment. Where does that come from . I think i was born with it. My parents had good judgment. You know the difference between right and wrong. Sometimes its as simple as that, just right and wrong. Charlie your instinct is right there. Mmhmm. I think that the thing that develops judgment is when people give you the room to make decisions, and you have to sit down and critically think about all of the options and the consequences and the sides of each one. When i met the president , he didnt know me at all. You assume because people give you a good reference that this woman must have good judgment, but i think weve also developed, you know, my judgment is good judgment for him. I think that i mean, in life i think i have good judgment, but the two of us together, i think we understand each other, and i understand what hes trying to do and how to get there. Charlie Alyssa Mastromonaco for the hour. Next. Theres a saying around here you stand behind what you say. Around here, we dont make excuses, we make commitments. And when you cant live up to them, you own up and make it right. Some people think the kind of accountability that thrives on so many streets in this country has gone missing in the places where its needed most. But i know youll still find it, when you know where to look. Captioning sponsored by Rose Communications from our studios in new york city, this is charlie rose. Charlie Alyssa Mastromonaco is often called one of the most powerful people in washington you havent heard of. She is the White House Deputy chief of staff of operations, one of president obamas longestserving advisers. At the white house, they say basically nothing gets done that involves the president doing anything without alyssa being part of it. Alyssa decides who the president sees, talks to and appoints. She weighs in on strategy. After coordinating the obamas lives for so long, she has become like family. She started working with then senator obama in 2005. Next came the campaign, and soon the white house. I barack obama do solemnly swear charlie she leaves this may. She will remain engaged as an outside advisor and help plan obamas postpresidency. We talked last week at obamas old Senate Office now occupied by senator brown from ohio. We started at her old desk. So this is it. This is it. Charlie this is where young senator obama had his four key staffers. Me, jon favreau, tommy vietor, robert gibbs and pete rouse. Charlie so former deputy chief of staff. The secretary yeah, he did okay. Charlie every time i read a piece about you, it talks about power. Okay. Charlie tell me what you do. What i do so i think that the reason people think i have power is that im the person that everyone comes to. I have the answer for everything. Charlie we have been looking for you. All over. I think the reason people think im so powerful is because they dont know what i do, and that mystery, which i have kept for good reason over the years, just really intrigues people. Charlie it gives you power. Exactly. But at the white house, the deputy chief of staffs job over the years has had many different permutations. I run the campus of the white house that includes air force one, camp david, marine one, the personnel, their 1700 fulltime employees in the executive office of the president. We run the searches for cabinet secretaries, we run the president s schedule, how he uses his time, who he sees. All those things because theyre so hard to define. Charlie you decide who the president of the United States sees. Theres a group of people. I cant take credit for it all. Charlie you decide where and how he goes. Yes. Charlie you decide whos going to be in his cabinet. Yes. Charlie youre more powerful than they even say. Thats generous. Charlie somebody calls you scary powerful. That was probably a friend. Charlie now, what did the president say about this . He said, at one point, as soon as they see you, all your power will go that is so this is true. Ive had it said to me by quite a few people that because so much of my job there are a lot of external folks. Im a very internal person. I dont do a lot of public speaking. This is the first interview ive done in eight years. But when im on the phone, i think i sound like the booming voice of oz. When people see me in person, i think someone once said i look like sally field in the flying nun and i should stay behind the curtain if i wanted people to be scared of me. Charlie why do you think the president of the United States trusts you so well . I think its all part of the journey and people sort of really are tested and prove themselves. When we got to this Office Charlie this was his office when he was in the United States senate. This was his office in the United States senate. When he came here, there was a group of people. Some he had known for a year or two, some longer and some of us brandnew to him. Over the years of decisionmaking and navigating tough times, your metal is really tested, and i think i proved to him that his success was my number one priority, that my hard work on his behalf wasntselfinterested and that, you know, i had good judgment. Charlie judgment. Yep. Charlie where does that come from . I think youre born with it, generally. I think my parents had very good judgment. You know the difference between right and wrong. Sometimes its as simple as that, just right and wrong. Charlie your instinct is right there. Mmhmm. I think that the thing that develops judgment is when people give you the room to make decisions and you have to sit down and critically think about all of the options and the consequences and upsides of each one. So when i met the president , he didnt know me at all. You assume because people give you a good reference that this woman must have good judgment, but i think weve also developed, you know, my judgment is good judgment for him. I think that its also i mean, in life, i think i have good judgment, but the two of us together, i think we understand each other, and i understand what hes trying to do and how to get there. Charlie i want to come to the president in a moment, but it began here when he was a senator. Yes. Charlie you were on the scheduler on the john kerry president ial campaign. Thats right. Charlie and the campaign does not end well. Does not end well. Charlie you had the terrible job of packing up. It was awful. You never want to lose a campaign. It was a really sad time, and i felt like it was my duty, my loyalty to john kerry that i wanted to make sure we wrapped everything up right, and we had an office, i think on connecticut avenue, and one day i was sitting there alone typing on my computer and an instant messenger window popped up, going back to aol, and it was robert gibbs, and he hadored for senator obamas campaign in illinois in 2004, and they were getting his office up and running, and he said, i think you might need a job. And thats how i charlie you said, you have been reading my mail. I said, id love to talk, and that was the beginning. Charlie what did you know about barack obama . Actually pretty funny, i did not know that much about barack obama, but since he was in the middle of his senate race since john kerry was only running for president , we crossed paths. When we went to chicago, we did an event for obama, and he asked secretary kerry to do a radio call while he was in the state with him. We get this email back and it says barack obama has asked j. K. To do this radio call. I thought, this isnt how we do things. We dont do things fly by the seat of our pants, and i was really upset about it. A couple of months later, we were in boston, getting ready to go to the convention, were all packing our bags, and we hear it must have been tuesday night as were packing, we hear this speech coming from the television, it was the second night of the convention, and it was barack obama, and we couldnt believe it because, of course, you know, theres the keynote and charlie i was there. It was incredible. We thought, oh, my goo goodness. Charlie and he was a state senator at the moment. Yes, and it was the most incredible speech. Charlie you were drawn to it . I remember exactly where i was in my apartment when i heard it. Charlie what is it about him . He is so authentic. A lot of the things that people criticized him for you know, he was too new to run, he hadnt been in the senate long enough a lot of those things were the attributes that made him such an authentic candidate. We didnt have the national, political roots. There werent people that we had sto say they supported us for x number of years so we had to fill in the blank. We were unfettered. We could do what we wanted to do. It allowed him the space to say what he wanted to say. He was either going to win his way or not winners and not winning was okay, as long as we tried our way. Charlie it would not have been okay with you, not winning. It would have been two in a row, and people probably wouldnt have hired me ever again, but the thing that made that campaign so fun is the mood from the top. It was we were going to do it totally authentic, he was going to talk to the voters, say what he wanted to say, and david, he was sort of our internal north star a. Thats what was fun because you never had to fake it. Charlie but from this office you had you, the speech writer jon favreau, robert gibbs Charlie Robert gibbs, the press person. Tommy vietor. Charlie tommy vietor the National Security security council. And pete rouse. Charlie later went to the white house. Counselor to the president , just left a couple of months ago. Charlie but you bond in a campaign, you test each others metal. But you had that before when he was out on the road selling his book. It was in the fall of 2006, hope came out, and there were midterm elections. We campaigned for about 30 candidates. Charlie anybody who called. Any democrat that wanted our help, we helped them. There were about 30 people we campaigned for. Charlie did you know he was going to run for president at that time, that you would be part of this . I was always very cautious. The whole reason i thought working for barack obama was a good idea was because i thought, after running for president , i would love to work for someone i knew wasnt going to run for president. Even the political plan because in 2006, i transitioned to his Political Action committee, and the plan that i wrote for us was the plan for the best person not running for president. And i wrote that in july of 2006. So we really didnt think that this was going to happen. But when senator harken asked him to come to the steak fry which is a tremendous honor, very big deal in iowa. Charlie just happened to have a caucus there, too. We said, lets go, well try it. It will be great. I had been to iowa a few times before in other capacities, and it was different. Charlie how was it different . It was folks in iowa test you. They want you to prove yourself. It is rare, i think, that you get such an outpouring of enthusiasm, and people who are just people were just so excited to meet him. That day, robert gibbs and i were both with him in iowa, and we were, like, oh, my god. Charlie oh, my god what . What if this happens . What if he runs . And i dont even know if it had crossed his mind. Charlie to run . When we were sitting there this was fun. We were on the campaign trail. We were, you know, going to keep the senate, take the house, i mean, thats all we wanted to do. This was just it was unexpected because its not what we sought out to do. It wasnt, like, a threemonth plan to see how iowa goes. Charlie in 2006 . In the fall of 2006. December 17th. Charlie two years later, you win the presidency. Mmhmm. Unlikely. Charlie and there are only what were now in 2014 there are two years left. Yep. Charlie and youre leaving. I am. Charlie why . Because i think that you know, especially as i tell you these tales of us over the past nine years ive had an incredible journey, and i think that someone else deserves the chance to have the experiences that ive had. Charlie and the person succeeding you is a longtime veteran of the obama team. She is an old obama person. She and i became friends when i sat at that desk out there. She was our downstate director in illinois. Charlie did he have any hint this was coming when you walked in and said, im gonna leave . I think so. I mean, when you get ready to leave the white house, you dont go in one day and just say, im leaving. Charlie you dont do that, do you . You dont do that. So i had sort of previewed several months prior that i thought my time was coming. Charlie he knew what that meant. Mmhmm. Charlie did he try to talk you out of it . Of course. Of course. But he knew. He newel yeah. Sometimes its just i think that he knew that, for me to actually get to the point where i said, you know what . Its time. That he understood. Charlie you got married in what year . Six months ago. Charlie how long was the honeymoon . There hasnt been one yet. A point i made when i talked to him. Charlie your husband is chief of staff for senator reid. Yes. Charlie majority leader of the United States senate. Yes. Charlie there mustnt be a lot of offtime between the two of you. Theres not. When we come home at the end of the day, theres a lot of work talk sometimes. Charlie pillow talk is a lot about politics . More about who did what to who. Charlie who screwed who today . Im not going to put it that bluntly, but, you know, we definitely charlie so you relish the fact that you might have done in somebody yes, theres a reason at the end of the day that i come home and charlie and you wonder why theyre scared of you . No, not like that. I mean, democrats have many priorities, and sometimes the white house and the senate arent always aligned, and, so, theres a lot of discussion about that sometimes, which is why i choose to watch, like, the Mindy Project and shows that make me laugh. Charlie i love her. She just was on the program. I saw that. She was hall hilarious. So great. Charlie take me to this moment. Sure. Charlie youre laying in bed together and you talk about who got whom today . Its more like a blackberry and an ipad charlie who has the blackberry . I have the blackberry and he has the ipad. He says, did you read this and see what so and so said . I said, i dont care. And i said, have you seen this . And he doesnt want to talk about it. So sometimes we have a time out. Charlie have you stayed behind the scenes on purpose . Yes. Charlie because . Because i think there are people in the administration are fundamentally outward facing and folks who should be internal. I think that, when youre talking about, you know, some of the things that i do, there is no reason for me to be external and, so, i have just chosen to keep my head down and do my job as i see it. Charlie you were satisfied knowing that you were one of the most powerful women in washington . I know i would be one day. Who wants to do anything else when this is the capstone of my career. Charlie i made you that night in new york, didnt i . Im hooked forever. Charlie so youve had this amazing life and you go in to the president and you say, you know, this is time. Its time. Charlie its time. And he knows its time. Mmhmm. Charlie he understands that. He says an interesting thing. Mmhmm. Charlie im not gonna let you go. Right. Charlie unless you promise me you will be there for me yeah. Charlie not only during the presidency, but in the postpresidency. Yes. So charlie i mean, thats an ultimate act of respect. I dont want you in my life just now, i want you in my life the rest of my life. It makes you realize that were just linked. We have been through a great adventure and what he said was, you can go and you can take some time off, but, you know, were together forever and i need you around. He said, you have to tell me that thats the deal. I said, of course. Charlie there is also this it hasnt turned out exactly like you two imagined it would. No. Charlie tell me about that. Well, when he first hired me, he wasnt totally sold on me. Pete rouse convinced him. Charlie because you were d. C. And he wasnt really interested in d. C. I was d. C. He wasnt really interested in d. C. , but pete rouse said, trust me. Pete rouse. Charlie and the president trusted pete rouse. He did. He said, okay. Charlie ill take her. Ill take her. Charlie i know and he called me. He called my cell phone, and i didnt recognize the number, so i didnt pick it up, but it was him. He called me himself, which was such thats not something a lot of people do. Charlie said something right there. He said, alyssa, lets do this. Its obama. Call me back. And that was it. Charlie now, go forward to the time that you had during the campaign rented at 30,000 a plane. Mmhmm. Charlie turns out, you rented that plane for the wrong day. Yeah. That was actually the fall of 2006. Charlie yes. During our campaigning for everyone. The whole front political office, it was three or four people, probably, five people, and i was doing the book tour and all the political travel myself and i made a big mistake and i rented the plane for the wrong day and i cried in the office and called robert and jordan kaplan, the finance director, and i said, im so sorry, the planes not there, i booked it for the wrong day. And i was so upset. And president obama takes the phone and he says, hey, i hear tears. I was like, yes sniffling theres a commercial flight leaving in two hours. Charlie back to it hasnt turned out like you two imagined. You thought you were going to ride into washington and eliminate partisanship. You thought you were going to ride into washington and do great things. You thought you were going to ride into washington and really i think the presidency was not worth having unless you did great things. Mmhmm. Charlie assess that for me now. So, one, when we were on the campaign, he always said, change of heart. You know, if a voice can change a room, then, you know, everything builds and builds. I think he was always honest with our supporters about that, how hard it would be. We got to washington, and its been hard. But when you think about the sort of lack of bipartisanship, hes still gotten an incredible amount done. He saved the economy from the the American Economy from going into a great depression, and the war in iraq. I think as of this afternoon, 7. 5 Million People have healthcare. So it may not be this vision that we or americans had, that it would be a kumbaya, hands across america, you know, its like one party. But i do think weve still gotten a lot done despite that. Charlie if thats true, and it is true, why are his polls so low . I mean, i d