My first question was: “How do you decide who gets West Wing office space?”
Jim laughed. “That’s the hardest one, and it sucks.” I would soon learn this myself. Besides that, he offered no counsel other than “You’ll figure it out” and warning me to double-check the roster of names for any military air requests—the “manifests”—to make sure none of the Cabinet secretaries was trying to sneak friends on board. After that, I was on my own.
My assistant, Dan Brundage, helped me organize all the briefing binders the departments that reported to me had submitted so that I could brush up on things: Office of Management and Administration (which oversees the Executive Office of the President, the budget, White House personnel, and the work on the 18 acres of land surrounding the house); Presidential Personnel (responsible for the nominations and appointments of political staffers in the agencies, many of which require Senate confirmation—everything from the secretary of state, to ambassadors, to placing people on boards and commissions); and the White House Military Office. Scheduling and Advance and the Secret Service got a break, since I already knew about them.
George Mulligan oversaw the WHMO. The WHMO works with agencies like the Department of Defense to run classified construction projects and maintain the continuity of government exercises—basically, if there is a nuclear attack, or DC floods, or the president is incapacitated, what does everyone do? The WHMO has teams to fly and maintain Air Force One and Marine One; they run the process for replacing or upgrading those aircraft and do upkeep for Camp David. They manage both the nonclassified and classified operating budgets—which means the money you can know about and the money you can’t—for all of the above. The military aides to the president and the presidential valets, who help with his personal needs, were also part of WHMO, as was the White House Medical Unit.
Of all the departments, I thought the WHMO would be the toughest nut to crack—it was complex, scary, and procedural, and there was no cheat sheet to understanding it. You met with WHMO in a conference room in a part of the White House that you’re not really supposed to talk about, and I would often be seated with high-ranking military advisers and decorated generals. I was worried I was going to look like a complete amateur when I had my initial briefing with them. It was scheduled for the first week I was deputy chief.
Before the meeting, my assistant went through the WHMO binder and highlighted some things he thought seemed important. Then I went through it—I was trying to absorb everything before my briefing so I would look totally in control. About an hour beforehand, I realized that was not going to happen. The binder looked like a prop in a serious movie based on a John Grisham novel. It included sections on construction projects; AF1 replacement; the helicopter (HMX) replacement program, which had been stalled; the operations of the Navy Mess; and the White House Communications Agency, which is the group that runs all the telecom for the president and on campus. This binder was so big it didn’t even fit in my bag.
I restrategized. I went through the binder and tabbed all the things that made the least sense to me.
When I walked into the secret room you’re not supposed to talk about, they had set me up at the head of the table, and I was the only woman. Everyone was wearing a uniform; I was in a Kate Spade outfit that may have involved a shirt with hearts on it. POTUS would have gotten a particular kick out of the fact that they either called me “ma’am” or “Deputy Chief.” (Luckily, he wasn’t there.)
They asked where I wanted to start. I opened up my crazy-looking Post-it commercial of a binder and began with the first question, which was about the helicopter replacement program. After they gave me answers, I had more questions. I think the meeting lasted two hours.
But about 30 minutes in, I got into the groove. The questions kept coming, and so did the answers. Before I knew it, I was understanding it all.
There is no bigger compliment than being intellectually curious about what someone else spends his or her days doing—it turned out that not having the answers did me no harm. The feedback I got was that the WHMO directors all “felt good about my leadership.”
CHAPTER 2
Preparedness, or The Patron Saint of Digestion
Everyone thinks that traveling with the president has got to be a sweet gig—lush service, pampering, the nicest meals. It is not. Stops in each location usually last for a day, two days, something like that—it’s not exactly a vacation plus a couple of casual appointments with world leaders thrown in. Everyone is working, trying to coordinate diplomacy, and thinking about what they have to do next. You’re so busy that it’s not always clear when you’ll get to eat—sometimes you’ll go the entire day without a meal.
One of the last trips I went on with POTUS was when we went to Europe in 2014. We were gone for about a week, and we visited the Netherlands, The Hague, Belgium, and Italy, where we were making a quick detour to meet Pope Francis at the Vatican before a lunch with Prime Minister Matteo Renzi in Rome. A photo of me asleep on a couch at the EU in Brussels sums up how we felt at the time: Sometimes you crush the trip, and sometimes the trip crushes you.
The morning of the meeting with the pope, the most exciting part of the trip, I went downstairs to the hotel restaurant to get coffee. I hadn’t planned on getting food, but in a moment of weakness, I ordered some eggs, too—I figured I wouldn’t get the chance to eat again until dinner.
Eating eggs is unfortunately not a benign act for me—I have IBS. It mostly flares up when I’m anxious or stressed, and traveling with POTUS, I had to learn to manage the constant possibility of almost shitting my pants in high-stakes situations. In a foreign country, you always want to eat the local food—the sickest I ever got was at the Raffles in Singapore because I ordered their take on chicken Cordon Bleu. But I am also just not good at handling eggs.
Why did I get them? I don’t know. It was a rash decision. I was coming up on my last month as deputy chief, and I was letting my guard down. My stomach started making noises while Ferial Govashiri—also known as Pho; she was Obama’s personal aide and my former roommate—was pinning a mantilla on Susan Rice.
“Alyssa,” Ferial asked, “did you eat something for breakfast?” Ferial was very familiar with my digestion issues. I told her I’d had eggs and coffee. She looked really disappointed in me.
When we got to the Vatican, I started to sweat. If you’ve never been to the Vatican before, you’ll think it’s lame when I say that it feels like you’re in The Da Vinci Code, but that’s the best nonreligious reference I have for the grandness of it all. The paintings, the architecture—you don’t have to be Catholic to think it’s incredible. It’s an overwhelming place to have an IBS attack.
President Obama was scheduled to have a private audience with Pope Francis, and senior staff were set for a semiprivate audience. We walked through a series of ceremonial anterooms and then lined up in precedent order (John Kerry; Susan Rice; me; and Dan Pfeiffer, Obama’s senior adviser for strategy and communications and one of my best friends) in an ornate hallway to wait for our turn.
This was the moment when I had to do some reckoning. What are my priorities? Am I going to tell someone I’m about to have diarrhea at the Vatican in hopes of getting help? Or am I going to keep quiet and potentially shit myself? Which is the least worst option? I didn’t know how long Obama was going to be in there, and I didn’t want to miss my chance to go in—you can’t just walk into the pope’s chambers late. I tried praying to the patron saint of digestion—there are actually a few who specialize against stomach pains—but I felt no relief.
I told someone. By this point in my career at the White House, most of the senior staff knew about my IBS; I once had to have Ben Rhodes, the deputy national security adviser, watch the bathroom door for me at Hamid Karzai’s palace while two Afghan guards played cards and smoked on the other side of it. This kind of thing really breaks down barriers with people. When you tell someone, “Here’s the thing: I might have to shit on this helicopter,” and
they don’t shun you afterward, you have a friend for life.
The team sprang into action, but they couldn’t find a bathroom in the building. I freaked; POTUS was due in soon.
Finally, a junior staff member came back with some good news and bad news from the doctor.
The good news: They had president-strength diarrhea medicine.
The bad news: There was no water anywhere.
At this point, I was vaguely aware that a sense of urgency had spread through much of the traveling staff, including most of the people who reported to me: They were all engaged in the mission to find me a glass of water so I could take the emergency medicine for my impending diarrhea. I concentrated on not shitting my pants on holy ground. After what felt like 12 or 13 hours, someone came in with a glass of water.
“Where did this glass of water come from?” I asked.
No one would say. All I know is that it was a glass of water in the Vatican, and I drank it.
You meet a lot of famous, important people while working at the White House, but meeting the pope was the first time that I really felt moved. The meeting was nothing elaborate—you walk up; shake his hand; say, “Your Holiness, it’s an honor”; and then you move on—and I’m not religious. But some of my family and many of my friends are Catholics, and I was struck by the sense that meeting this person would mean so much to so many people. I felt lucky.
After that, I had to go lie down in the car. Like all our drivers, the driver was a member of the military, and I always felt very embarrassed when I had to expose my digestive weaknesses to them. (My pants were also unbuttoned.) He asked me if I was OK and if he should get the doctor; I told him no. As I flung myself over the backseat, I felt something poke me in the leg. While POTUS was meeting with the Vatican’s secretary of state, I had taken, like, five packs of the blessed rosary bead souvenirs they give to people at the exit, and they were all in my pockets.
I have always liked the feeling of being prepared. Preparation is protection you can create for yourself; for some people, the hard part may be balancing precautions with paranoia, but in my experience, you can never be too prepared. I’m talking about everything from always carrying a weird sack of stomach aids—I personally like to have Imodium and Gas-X on hand, along with some Xanax (red wine also works but is harder to pack)—to patchouli, which has the benefit of both smelling good and calming me down. I also read every bit of information I can find on someone before I meet that person, and I always read the newspaper. If you skim the actual paper—the one that is printed and that you can hold in your hands—you hit on things you would never seek out on a website. If I went through life cramming like every day was the SATs, it would be a miserable existence, but being in control and taking a beat to think about the next five steps—about what comes next—is critical. You would be surprised what five minutes here, 15 minutes there, can do to make you feel confident and ready.
When Obama was a senator, his foreign travel logistics were handled exclusively by the Senate Committee on Foreign Relations (SFRC). Aside from getting him to O’Hare (which he usually did himself), I had no real idea what a foreign trip entailed when I got to the White House. Except for one previous kind-of-traumatizing experience.
During the campaign in 2008, we had mused about taking Obama on a foreign trip to demonstrate how beloved he was abroad, to show he could handle it, and to dispel any ideas that he did not have foreign policy prowess. But it took us so damn long to officially become the Democratic nominee (June) that I assumed we wouldn’t be doing the trip. Our planning window would be so short, and I thought the campaign would want to focus all our energy on rallying the American people—the ones who could actually vote.
Oh, not so.
It was nighttime in the second week of June, and we were doing a conference call with Obama. The foreign trip was on the agenda, but I assumed the call was intended to officially drive a stake into the idea and move on. By the time I dialed into the call—a few seconds late—the discussion had already gone from a possible trip to the UK and Germany to a trip to Iraq, Jordan, Israel, Germany, France, and the UK. If the phrase “LOLZ” had existed back then, I would have texted it to everyone on the call. Instead Plouffe asked me what kind of crowd I thought we could get in Berlin, Germany. “I can tell you about crowds in Berlin, New Hampshire,” I said, “but I have no idea what we could do in Germany.”
Nevertheless, the trip was on.
I went to bed and woke up early. This was a situation that would need to be triaged.
The next day I assembled the SkedAdv team to deliver the news to them. Emmett, Dey, Jess, Big Liz, Astri, JoeJoe, Pho, Chaseh, Tedders, Nool, Teal, Q, Levitt, Donny, and Little Kate the intern. I think Lesser, Lillie, and Tubman were on the phone. They would have about a month to plan a trip to six countries; it was an ungodly amount of work.
But the team was beyond stoked. Everyone started shouting ideas for things that we should be thinking about. Passports, visas, translators, hotels, volunteers, per diems, translating baggage tags! Executing a foreign trip as a presidential candidate means you’re not entitled to support from the US embassies in each country. We would be doing this alone—essentially as tourists. There was no time for ego.
Everyone had his or her own discrete function. First, Denis McDonough, a senior foreign policy adviser, and Ben Rhodes, then the campaign’s foreign policy speechwriter, assembled our “country captains”—foreign policy experts who helped each team navigate their country.
Peter Newell—Nool—was the director of press advance and worked on all the logistics for the press that traveled with Obama. This included things like accommodations and visas, but it also meant everything from working out where Katie Couric would do her interview with Obama in Israel to making sure the hotels we stayed at could accommodate satellite trucks for live stand-up interviews. Nool also made sure the press were well fed (a hungry press corps is bad… news) and had the right setup everywhere Obama went.
Ted “Tedders” Chiodo oversaw travel logistics and secured all our hotels and visas. We sent Tedders from Chicago to DC with a sackful of cash and 60 Jordanian visa applications to be expedited. Not a single peep from TSA.
We decided our big speech would be at an outdoor event in Berlin, and we sent my deputy, Emmett Beliveau, to Germany to scout a location.
Dey, Jess, and Lizzie Nelson would run the trip—because of the time differences between Chicago, Europe, and the Middle East, this would need to be a 24/7 operation. Since Little Kate (Kate Berner) was the youngest, she was in charge of technology (BlackBerries). Each country’s advance team had an anchor member who could speak the local language.
As we were transitioning from the primary to the general election, we upgraded from renting charter planes to leasing a dedicated Boeing 757, which we had to reconfigure with better seats, including a private space for the candidate. That was my job, in addition to overseeing the execution of the trip. When I told Plouffe we would need this plane, he looked up briefly from something he was typing and said, “How much?” I told him I thought that, all in, including painting the plane with “Change You Can Believe In” and reconfiguring it back to its original formation when we were done, it would come in at around $3 million.
“Fine.”
When I told him that I had gotten a deal on captain’s chairs for Obama’s cabin, he looked up sharply and said, “How much did that cost?”
I admit, I brought this up almost entirely for the glory. I beamed as I told him I had purchased the old chairs we bought for John Kerry’s 2004 plane for about $3,000 each. That was dirt cheap. He said, “Good.”
The plane was going to be delivered to Chicago about three days before we needed to take off for the Middle East. About two days before that, they sent me a picture of the newly painted aircraft. Beautiful—except the font was wrong. Here’s the thing about being a decent businessperson: When you are reasonable, savvy, and polite, you get far. I had a good relationship with the plane guys, an
d I didn’t scream at them when I saw the wonky font. I told them nicely that they had to repaint the entire plane using the Obama-ified Gotham typeface—and fast. They did it.
Eric Lesser was in charge of luggage logistics. He was a Harvard Dem in 2007 and had former New Hampshire governor Jeanne Shaheen call me to get him a job doing anything. He flew with Obama and the entire traveling press corps and never lost a bag. Ever. During this trip, he organized luggage volunteers around the world and had our baggage tags translated into five languages. (Now he’s a state senator in Massachusetts.)
A few days before the advance teams were ready to depart, I came into the campaign office and saw four big moving boxes and Little Kate on the floor, eyes wild. Kate was a junior at the University of Chicago, took the summer to intern for the campaign, and somehow ended up with us. In those boxes were about 75 BlackBerries sorted into various categories—“programmed,” “advance staff,” “traveling staff,” etc. In 2008, our BlackBerries didn’t have international capabilities, so we rented a shit ton of devices that did work abroad, and Little Kate manually programmed the entire staff’s 75 numbers into every single phone.
The day before the rest of us were leaving, I had Little Kate run training seminars for all the senior staff on how to use the phones. Never was I prouder than when I heard her chasing David Axelrod down the hallway shouting, “Axe, wait! I need to show you how to use your phone!” (After graduating, Little Kate spent several years at the White House.)
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