Who Thought This Was a Good Idea?

by Alyssa Mastromonaco

  Whenever my friends or family would ask me about whether Obama was really considering running, I would pretend not to know anything. I became a recluse and spent a lot of time in my apartment, going over every single thing I would need to set in motion if Obama came back from Hawaii and said, “Let’s do it.” I had notes posted all over my living room.

  Hope Flood became the Obama Exploratory Committee headquarters on January 16, 2007, and it was one of the most exciting days of my life. Reprogramming the fax machine to say “Obama Exploratory Cmte” was exhilarating—I know it sounds ridiculous, but it really, really was. My weeks of reclusive brainstorming had paid off: I had a detailed time line of everything we needed to do. (Reprogramming the fax machine was on it.) Hope Flood wasn’t posh to begin with, but it was transformed into a shelter for young fund-raising staffers, who sat around with their computers on their laps because we had no desks. I was still the political director for the Hope Fund, but that would soon change.

  We all began to trawl craigslist looking for apartments in Chicago. The one bedrooms were really shitty and expensive, but the two bedrooms had potential. I saw Smoot on the phone with donors in the corner of the office; immediately, I eyed her like prey. An adult roommate would be my path to a sweet living situation.

  When she walked by my desk, I turned around and said in my most casual voice, “Hey, Julianna… do you know where you’re going to live in Chicago?”

  “No,” she replied. “I have no goddamn idea.”

  My opportunity to strike. I asked her if she wanted to be roommates.

  “Fine,” she said.

  “I have a cat,” I said.

  “Fine,” she replied, and walked away.

  Smoot did not have time for pleasantries. She had just learned that our political email database had about 10,000 contacts in it. I thought that was a good thing; Reggie and I had been so slick in getting email addresses at all the events Obama attended that fall. But apparently it was anemic.

  I started looking for short-term, furnished apartments—after all, I figured the chances that we would be out there for the entire two years before the election were pretty slim. We were very pumped, but becoming the Democratic nominee was a long shot.

  At the same time as I was wrapping up life in DC, Cara, my best friend, was getting married. Her bridal shower and bachelorette weekend were right after we formed the OEC, and I was the maid of honor. On the train to BWI to go up to New York, I was on a conference call about the event where Obama would announce he was running for president. My phone cut out at the end, but I was almost at the airport, so I figured I would be able to get debriefed after I made it through security.

  When I got to BWI and was standing in line for security, my phone rang. It was Larry Grisolano, one of Axe’s partners. He told me what they had decided: Instead of one announcement event in Springfield and a second over the border in Iowa, which is what we had planned, they would do one event in Springfield, three in Iowa, one in New Hampshire, and one in Chicago. Over the course of three days.

  At that point, I was the only person working in scheduling and advance for the exploratory committee. We didn’t even have a credit card yet. It would fall on me to plan this.

  I asked if he was trying to say they wanted a chartered plane for the whole trip, which would begin in about three weeks. Yes, that was what he was trying to say. They intended to transport press and some supporters, friends, and family, and this inevitably meant more staff would travel as well. I knew I was looking at managing the logistics of an additional 30 to 40 people more than I had planned. I would also have to find a plane big enough, on short notice, and make sure it could land in the airports near the cities they had picked and make sure those airports had stairs that fit the plane, which is not always the case.

  I sat on the floor of BWI and started to sob uncontrollably. I couldn’t believe how little concern they had for the amount of work this meant—not just work, but magic. TSA agents had to come sweep me away. They asked what was wrong; I told them I had to get a chartered plane with no credit card or stairs. They looked at me like I was insane and walked away.

  I also needed a staff; where I would find one was less obvious. The scheduling and advance world was made up almost entirely of people who had cut their teeth with the Clintons in the ’90s. The Hillary team had already started recruiting, and the message was clear: Do anything for Obama, and you are dead to us. I was screwed. My message was, “Dear God, please help me. I trust you enough to do Clinton events, too, please just help me, please, please, please.”

  It was the worst possible time to be heading up a raucous ladies’ weekend. I landed in Albany and picked up the bachelorettes’ white mega minivan—“the Vangina”—and I had coordinated the rest of the gang’s train arrivals and pickups at the Poughkeepsie and Rhinecliff train stations. My mom was picking up all the booze, and my dad was making Cara’s favorite pizza. The only thing I cared about was making this weekend great, and I knew the only way to make it great was to ask for some help and give orders.

  There was no cell service in the house we rented, so each morning I got up at 5:00 AM and went to the house I grew up in—conveniently down the street—to check my email and phone messages. I answered everything and explained when I would be back on the grid. I kept a running list of what I needed to do and I got it done. As I type this, I feel like I should apologize to Cara for what was probably a ragtag bachelorette weekend.

  Still: We ate, we drank, we cruised around in the Vangina. I think I kept it together and showed my hand only when I passed out early on Saturday night. As for the charter plane and Obama’s announcement tour, I knew I had made it work at the end of the first full day. We were staying at an AmericInn in Iowa, and I was following Obama down the hallway when he turned around and said, “You’re pretty proud of yourself, aren’t you?”

  CHAPTER 7

  Humility, or Changes We Can Believe In, Sort Of, If We Have To

  When Obama became president-elect in 2008, our team went through a big shift. The period between Election Day and Inauguration Day is appropriately referred to as “the transition,” and there are two entities that support the president-elect during this time: the Presidential Transition Team (PTT) and the Presidential Inaugural Committee (PIC).

  We were all friends, Obama included, and although we were working for him, he always maintained a casual atmosphere—even in moments of crisis. Once, he asked me if I was angry with him because, in the Senate, I would refer to him as “Senator Obama” instead of “Barack.” He was not one who engaged in or enjoyed formality; later, when he was the president and I was deputy chief, Nancy-Ann DeParle and I would often ride in a different car when we all went to meetings and events—so we could get work done and give him some privacy—and he eventually got upset and asked her if she didn’t like sitting with him. (She told him she assumed he’d like some time to himself.) But when I started working for him in early 2005, he was the junior senator from Illinois and the youngest member of the Senate. If people like me and Favs and Tommy ran around calling him “Barack” in front of people like Ted Kennedy and Robert C. Byrd, what reason would they have to respect him? (We ultimately brokered a deal that, in front of other senators, I would call him Senator Obama, but otherwise it was Barack.)

  During the transition, I worked for the PTT, but I also had a hand in the PIC. This wasn’t my ideal situation; the PIC would have been the cherry on top of the 2008 campaign for me. Preparing the inaugural events for the first African American president—there was nothing more important, or exciting, in my opinion. But Obama had asked me to stay in Chicago with him on the PTT while I kept an eye on the PIC. I knew that staying in Chicago was the most important thing I could do for my boss (this wasn’t my inauguration) and that my deputy on the campaign, Emmett, would be an excellent executive director of the PIC, so I let it go. Pretty easily.

  Generally, though, this was a very anxious time. First, neither group offers a permanent j
ob. You try to do your best on your current assignment—whether that’s PIC or PTT—but you can’t help but worry you’re somehow missing out on locking down a gig in the administration because you’re distracted by the president-elect’s immediate needs. You kind of have to have faith.

  Second, at the very end of the campaign, department heads—of which I was one—are given a grid on which they have to grade their staff. Unlike at Ivy League colleges—cough, cough—you can give only a certain number of As and Bs. I didn’t exactly know how the grade I gave people would be used, or know how much influence it would have on how my people would be placed—especially since I didn’t agree with having to give people Cs!—so I felt weird about this, too. Rumor had it that in previous administrations, scheduling and advance staff had gotten lost in the shuffle and didn’t end up with great jobs in the White House. So not only was I worried about myself, but I needed to make sure that my team was on the big radar.

  On top of all that, going to the DC PTT office felt like you were visiting a prison: You walked in and handed your ID through a plastic barrier, and then you waited in uncomfortable plastic chairs under harsh lighting for someone to come “escort you in.” You had to go through magnetometers. One day I walked in and saw Plouffe looking like he was waiting to be arraigned. The PIC was not better; it was in an old DC building that was hard to get to and had very little heat, and this was winter. Standard attire there was a hoodie over a suit.

  I spent most of November and December in the Chicago PTT office, which was where Obama was a lot of the time; it was a little better than the DC office. It was here that we would meet to discuss the short lists for positions in the Cabinet and who should come out to meet with Obama. We also brainstormed who would be great for which jobs, made lists for inaugural invites, and got a taste of what life in the government would be like.

  As a taxpayer, you’re probably stoked to hear that there is no “entertainment” budget for the PTT. That government employees have no way to expense food or drink or be reimbursed for boxes of tissues that they bought for the office when everyone had the flu. For PTT employees, it meant that we didn’t have glasses or pitchers to serve water; this may seem like the least of your necessities, but we had meetings and conferences with a lot of people there. Once, Ferial had to walk to Bed Bath & Beyond in a snowstorm to buy pitchers, utensils, water, and apple juice for a meeting we were having with then Senator Clinton. We still don’t know where the idea for apple juice came from—Senator Clinton was definitely not in kindergarten at the time—but it doesn’t matter: Ferial lugged it all back to the office. Each night after that, she and I took the pitchers and forks home to wash because the only sinks we had were in the bathroom, and they were too shallow and didn’t have hot water.

  All the support we’d had on the campaign—or even in the Senate—was stripped away. We weren’t exactly feeling like hot shit because we were about to go work in the White House. When Obama was having an economic meeting and heard it was Peter Orszag’s birthday—Peter was going to be the director of the Office of Management and Budget—he wanted to get a cake, and all we could think was, ARRRGHHHHH, plates?!?!?!?

  I also worked with Mel Winter, Michelle Obama’s deputy chief of staff, on coordinating some of the inauguration. Mel and I had to learn how to do Excel spreadsheets in order to make the friends-and-family guest list. (Don’t laugh—you can’t do them either, and this was in 2008.) She would read the names aloud from handwritten notes POTUS and FLOTUS had made, and I would type them in. We did this a lot. One day, we were going through POTUS’s family, who were traveling from outside the United States, and Mel read aloud to me, “Abongo Obama.” I said, “Is that with an O or an A?” Because the office was so small, Obama heard us and shouted back, “Are you making fun of my family?”

  He was just messing with us. Still, when Obama walked by, we no longer said “Hey” and kept working—we stood up. He would tell us to sit back down, but we always stood up.

  In late November, I was offered the job of assistant to the president and director of scheduling and advance, and I made the move from Chicago to DC in early December.

  It was strange to be back in DC. I had really loved living in Chicago, and were it not for us winning, I probably would have stayed. My apartment was in a new building in a sort of charmless part of town—13th and M Streets NW—but it was walking distance from the White House, so I signed the lease without seeing it. I bought my furniture from Crate and Barrel after two glasses of champagne, and after my years of moving around it was the first real furniture I had ever owned.

  As I pulled up to the PTT office on my first full day in DC, I saw Joe Paulsen standing on the corner, appearing to be hailing a cab. Joe had started on the campaign in Iowa. When the caucus was over, I was so impressed that I asked him to come work for me in Chicago. I had him handle highly complicated and sensitive situations, like the logistics around the Commission on Presidential Debates. When I got out of the car, we hugged, and I asked what he was doing. He was totally frazzled; he really was hailing a cab. But not for himself—for his new boss, who was on the national security team and whom I had never heard of. I was kind of shocked. Uh, David Plouffe hailed his own cabs, I thought. Who is the self-important nobody making Joe do this?

  That was the DC transition in a nutshell: I saw people I had found incredibly capable hailing cabs and making copies. My heart kind of sank. Was this how it was going to be?

  Sort of. Some of the “cavalry”—people who had served in previous administrations, who didn’t really respect us newbies all that much—seemed to enjoy being back in the saddle. Many of the people on the PTT team in DC were former Clinton staffers who were glad to be offered more work but didn’t have such warm feelings for Team Obama. One of the main things I remember is that they used acronyms we couldn’t decipher; BLUF (Bottom Line Up Front) is the main one. People would come at you like, “Give me the BLUF,” and we would all look at one another and mouth the words, “Do you know what that is?” I had a constant stomachache in this office.

  For two years, Plouffe had led a group that was structured but very open, and because of that—because he treated everyone equally—no one ever really fussed or jockeyed for power. We had run a campaign on believing change was actually possible. But Plouffe had almost nothing to do with the transition, so once we got to DC—which is hierarchical and patriarchal—it felt like the same old backslappy white-bro club. These old-school government hacks considered your career impressive if you had worked for several administrations, not if you had been on a campaign that had accomplished something many people had believed was impossible. This didn’t work in my favor. I was treated like I didn’t know what the hell I was doing, even though none of these guys had worked for a president in a post–9/11 world, when the kinds of events the Secret Service will permit you to do are fundamentally different from what they were before the attacks. My job required more creativity and planning to build great, impactful events—especially because the Secret Service was even less willing to do anything remotely risky with the first black president.

  My team had built a great relationship with the Secret Service during the two years we were on the campaign, and I knew we had a long time left together. So when someone on a conference call suggested that we have Obama do an event on the George Washington Bridge—yes, standing in the middle of the bridge—I didn’t hesitate to say it wouldn’t work. Even though I was right, I could hear people rolling their eyes over the phone; some of them actually continued talking over me. I will never know if it was because I was a 32-year-old woman or because I was a 32-year-old person or because I just didn’t have “White House” on my résumé, but my opinions were always discounted, when they were even solicited at all.

  I spent some time feeling very defensive and uneasy. Information was the tool I needed to do my job, and I couldn’t figure out where it was or how to get it. One day, Dey and I were talking about mapping out the first 100 days. Rahm Emanuel�
�who was going to be chief of staff in the White House—overheard us and said, “Mona has the block calendar.” This was shocking. We had always been the keepers of the block calendar—it was like the scheduler’s bible, and not just anyone could have access to it. We also had no idea who Mona was.

  We later learned that Mona was about to be announced as the White House deputy chief of staff for policy. Which was well and good, but why did she have our block? Why did Rahm have her start doing the schedule? By the time Mona left the White House two years later, we were buds and I lovingly called her Mo-Mo, but I never found out. Were it not for the team we had built—and the sense of community within our department that endured even though we were split between cities and offices—I think a lot of people would have bailed.

  As Inauguration Day grew closer, once a week or so, Mel and I would head over to the Hay–Adams Hotel, where the first family was staying with Emmett, to talk about plans for the inauguration. Those meetings were some of the few times things felt familiar. We would talk about who needed to sit where, the status of certain events, and things like who the Obamas wanted to sing the national anthem and read as the poet laureate. Soon, I realized that I would be too busy preparing for the first day in the White House to see any of it.

  As we headed into the holidays, things got into more of a flow, but I was fried. I went home to Rhinebeck for Christmas and acted like a real asshole—it was like I was getting my period for the first time. I was short-tempered, and my annoying, nitpicky attitude drove my whole family nuts. I started crying in the middle of Christmas Eve dinner. I was feeling so suffocated and overwhelmed by what was coming, but everyone was so proud of me. I should have been ecstatic, but I was mostly just scared. I didn’t know how to talk about it without sounding ungrateful, so I just lashed out.