Who Thought This Was a Good Idea?

by Alyssa Mastromonaco

  The properly painted plane arrived just in time, and it was a sight to behold.

  When we landed in Jordan, I was so glad to see Pho. Pho was born in Iran; when her family fled during the Cultural Revolution, they moved from Cyprus to Germany to Minnesota and finally settled in California. Before coming to the campaign, she had been the chair of the Orange County Young Democrats. She was on the Amman advance team and would be my lifeline on so many trips to come.

  It was hot as shit in Amman. We spent most of that leg of the trip in a conference room completing the planning for the next stop, Israel, which was going to be a feat. We were going from Tel Aviv to Jerusalem to Sderot, back to Jerusalem, up to Ramallah, back to Jerusalem, and then to Tel Aviv to leave. We did about 18 meetings and events in a 36-hour period. At one point, a car bomb went off a few blocks from the hotel where we were staying, and we couldn’t contact a member of the advance team for a while. Scary—but he was OK.

  We had a legendary advance guy leading the charge in Israel. He also did not mince words; at one point, way too late in the game, we were still negotiating whether to borrow helicopters from the Shin Bet, and he told one of our own people that if he didn’t shut up he was going to “sodomize him with a vacuum cleaner.” My main memory of this part of the trip is learning that stress can make your gums bleed. But by most other accounts, it was very successful.

  The next big hurdle was the giant event in Berlin, though I wasn’t too concerned—Emmett was already in Germany (and, I would find out later, completely worn out). While Israel was the most anxiety-inducing part of this trip, Berlin was the real critical moment—if we didn’t pull this off, if enough people didn’t show up, if the setup outside the Victory Column looked bad, we would seem like idiots.

  Rolling into Berlin, we heard reports that 100,000 people were waiting for Obama. We didn’t believe them, but it was true. Aerial shots of the crowd are insane: a sea of people, on tiptoe with cameras, trying to get a glimpse of the real Barack Obama beyond the series of giant TV screens broadcasting him to those in the back.

  I stood with Axe, Gibbs, and Susan Rice in the buffer zone behind the stage as Obama delivered a sweeping speech about how Berlin represents the importance of international cooperation (and, subtly, about how he could be an antidote to eight years of George Bush). I’d heard Obama give countless speeches, and he has always been a brilliant orator, but this one made me so proud; we knew Barack Obama was great, but to see all these people from other countries recognize it was moving. The event was so good that John McCain used clips of it for his “Celebrity” ad, where he compared Obama to Britney Spears and Paris Hilton.

  Afterward, everyone had talked a big game about going out. We were staying at the Hotel Adlon (where Michael Jackson dangled his son over his room’s balcony) across from the Brandenburg Gate; I went to my room, ordered a steak and wine, and passed out by 9:00 PM. The next morning, Marv got up at 8:00 AM to help me hunt for an apfelstrudel, which is something my Oma, who was from Germany, used to make for me. The one we found wasn’t as good as hers, but it was one of the best parts of the trip.

  The jaunts through France and the United Kingdom went without incident, and I slept from London to Chicago without waking up once.

  The trip was a very risky move. Taking a candidate out of the country four months before a general election can backfire in countless ways—in 2012, Mitt Romney’s own trip to London, Warsaw, and Israel was deemed a “Gaffepalooza” by the Washington Post; the UK tabloid the Sun called him “Mitt the Twit.” We pulled it off because we were prepared for anything that could go wrong—from massive security failures down to baggage tags.

  In late March 2009, President Obama decided to make his first trip to Iraq as president of the United States. As the director of scheduling and advance, I was head of the coordinating body—we worked with the national security staff, the White House military office, the Secret Service, and the White House staff—that was in charge of figuring out how exactly this would go down.

  When you send the president, or any distinguished visitor (DV), to a foreign country, it’s no light matter. I’m sure you remember seeing news break one morning about the president, vice president, or secretary of state having landed in Iraq or Afghanistan. In most cases, the president flies overnight so he can avoid anyone knowing he’s left the building, arriving as America wakes up so people with potentially dangerous motives don’t have time to plan anything extraordinary.

  It takes a lot to pull it off—you need to be able to fully trust your team to tackle the required choreography to get roughly 40 people (staff, Secret Service, press) into the air without anyone seeing. I thought that because we’d orchestrated the giant campaign trip the year before, we would be fine. This was not the case.

  In 2009, we decided that, since it was our first time going to Iraq, we should make it as hard as humanly possible on ourselves. We would jump to Iraq after we finished a stop in Turkey on a previously planned OCONUS (Outside the Continental United States) trip.

  In order to scoot out of Turkey and into Iraq with POTUS and a handful of staff, we pretended the backup plane (when you travel abroad, you always take two, in case one breaks) was broken, so we left without it and went off “back to DC.” This means that we lied to our own staff—we kept all the people who weren’t essential to staffing Obama on the ground in Turkey for a few hours, until we arrived in Iraq—and to the reporters who weren’t in our press pool. We gave the White House press corps—a group of 13 or so reporters who rotate in traveling with the president—a heads-up to include them in the planning process (and to give them the opportunity to go home if they didn’t want to head into a war zone), but it was under embargo, meaning they couldn’t report on it or discuss it.

  We were a couple of hours into the flight to Iraq when Emmett—who remained my deputy and became the director of advance in the White House after the campaign—called Air Force One to let us know a sandstorm was kicking up outside Baghdad. The thing about sandstorms is that they make it very hard to fly helicopters. Our plan had been to land at Camp Victory, our US base outside Baghdad, dash over to the helos, and take off as fast as we could for the Green Zone and our meetings with President Jalal Talabani and Prime Minister Nouri al-Maliki. We needed to figure out what the hell we were doing instead, and fast—you don’t dillydally with a POTUS in Iraq.

  As we huddled around the conference room table on AF1, Gibbs asked me what I had in my pockets. “Hmm,” I replied, pretending to root around in there. “Nothing?” He gave me a side eye, but we were in the middle of a phone call with General Raymond Odierno, who at the time was Commanding General, Multi-National Force, Iraq, to figure out a plan B for when we landed.

  Truthfully, I hadn’t given much thought to what I’d brought in my pockets, but there was something in there. I had never been on a helicopter before, and I was pretty convinced I was going to puke once we got in the air. I was the most senior woman on the trip (in a sea of dudes), and I didn’t want to embarrass myself (and the entire gender), so I went to Whole Foods before we left and stocked up on plastic produce bags. I carried them with me, stuffed into the pockets of my trench (I thought it had a Carmen Sandiego vibe) as a precaution. Instead of going with one or two bags, which would have been a reasonable amount of preparation, I probably had five or six and gave myself away. I looked like a college student trying to sneak cereal out of the dining hall.

  The sandstorm was quite bad—but I never saw it, because we ended up landing at Camp Victory and taking the motorcade, a line of black Suburbans and two or three white passenger vans. As I took off my jacket, I came clean to Gibbs and Axe, because a lie would definitely have been weirder than the truth. I explained that I was absolutely not going to be the woman who barfed on a military commander in Iraq, and they appreciated it.

  We arrived to greet the troops at the palace that used to belong to Saddam Hussein’s mother-in-law. So many surreal things happened. I don’t like to characterize some
one’s feelings about a situation, but I can say with some certainty that Gibbs was taken aback, and humbled, when the troops recognized and cheered for him. It hadn’t occurred to him that they would routinely watch the daily White House press briefings he gave.

  Rhodes and I sat on this really gaudy bench and waited. Then we hustled over to the general’s house, where the president had his meeting with other Iraqi leaders. We ended up having to do phone calls instead of meetings with President Talabani and Prime Minister al-Maliki.

  It’s common to keep your phones off when you’re traveling to a war zone, so no one can track your signal, but once the meetings were under way and the press had reported that Obama was in Iraq, I could use my phone again, so I called my sister. She answered the phone at work. “Oh my God, sis,” she said. “Are you in IRAQ?”

  We had only been in office for about two months, and I was feeling pretty cool. Although I didn’t end up puking on a helicopter, preparing for that worst-case scenario allowed me to focus on the “normal” concerns of my job. Knowing that if I puked, I would have been able to do so gracefully made the whole thing markedly less stressful.

  A BRIEF INTERLUDE FOR SOME MORE PREPAREDNESS TIPS

  A question women often ask one another is: “What do you do?” It may refer to a skin-care or exercise regimen, or a set of dietary restrictions, or how you manage to get out of the office with zero emails in your in-box, but I think the question—which basically boils down to “How do you live your life?”—is rarely posed out of nosiness. Maybe it’s genuine curiosity (which is different from nosiness). Maybe it’s the compulsion to make sure that you yourself are on the right track. (Am I right to hate myself for waking up late?) Maybe there’s a little desire to steal some aspect of someone else’s routine for your own life. (How can I stop hating myself for waking up late?) Regardless, the answer is rarely uninteresting, even if it’s totally boring. Here’s what I do to stay prepared.

  (1) I always keep a list. I love a good list. I separate it into three parts: immediate goals, long-term goals, and personal. The immediate category usually includes things like paying bills, buying cat food, making a hair appointment, or picking up a prescription. The long-term list would include things like figuring out how to register my company in New York State, paying off my car (I did it!), planning a vacation, and getting tickets for an upcoming concert. The personal is basically just a list of friends whom, during the business of my life, I don’t want to forget to call, get drinks with, or track down to get our nails done. Something like “write this book” would end up falling in all three categories and listed three times so that I would maybe get the message.

  Here is a sample list from today (August 15, 2016):

  IMMEDIATE:

  Finish chapter 6 with LO edits

  Pay Q3 tax bill (need to find envelope/must drop in Rhinebeck at dinner)

  Go to PetSmart (need litter and more food for Petey)

  Cut BunBun’s nails

  Shower

  430P call with Hope

  Get train tix for this week

  Put trash out

  Leave by 515P for din with Mom and Poof

  LONG-TERM:

  Update chapters 1, 3, 6 with LO edits

  Write chapters 4, 5

  Email Souza about photos

  Lock down Sept house for LO

  Make list of improvements to Germantown house

  See land in Germantown

  Figure out Poof b’day present

  Make hair appt

  Get car washed

  Try valerian root

  Make Petey annual vet appt

  Check to see if Ace+Jig coat has shipped

  Check to see if No 6 clogs have shipped

  Email Molly about CORA in Target

  Connect with Sophie Walker

  PERSONAL:

  Book shit

  Read The Girls

  Less carbs

  (2) I put everything in my calendar. It takes so much stress out of my life to know where I can find things. My credit score went up 100 points when I started putting in reminders to pay my bills. I put birthdays in my calendar and set a three-day reminder in advance so I can put a card in the mail. (I keep birthday and all-purpose cards in the house at all times. And stamps. You should always have stamps.) I schedule reminders to pick up prescriptions or to make a dinner reservation at some bullshit hard-to-get-into place where you need to book a table 30 days out. Same for hair and gynecologist appointments—anything hard to schedule. I put my grocery list in my calendar. I almost always need 2% milk, Wheaties, watermelon, coffee, Coffeemate (don’t judge), and grapefruit juice, so I keep the list to remind me in case I happen to find myself at the store.

  (3) Sleeping is good. For a long time, I was skeptical about those thousands of books that talk about the importance of sleep. When I worked at the White House, I started off going to bed at around 11:00 PM and waking up at around 5:15 AM, and because “going to bed” is different than sleeping, I probably slept only three to four hours a night. It was really after I turned 35 that sleep started having the greatest impact on my life, but keep it on your radar—you eat less, look younger, have a better attitude, and make better decisions if you get enough sleep. After I left the White House, even though by the end I was on a strict sleeping regimen (more on this later), I was finally able to sleep in a meaningful way, and it changed my life.

  (4) On traveling: No matter what I’m doing or where I’m going, I try to give myself as much time as possible to get there. (I am partially motivated to do this because I get stomach cramps or diarrhea when I cut anything too close.) If making an impression is important, I fly or take a train or drive the night before.

  I also learned the importance of packing from Dey. When you’re working in the White House, you can traverse three distinct climates over the course of a trip, so packing is vitally important. On one trip, we started in Saudi Arabia, went to Egypt, stopped in Germany, and finally ended up in France. You will never go wrong with lots of layers and always covering your shoulders.

  Because no one working in the White House had time to run around our apartments screaming, “Did I forget anything?” Dey had a packing checklist that quickly became legendary; after a year or so, we all used it religiously. Compression socks and a Snuggie (yes) for long flights. Granola bars for places with dodgy food. Tide pens. Bobby pins for countries with lots of humidity. Culturally appropriate footwear and dresses for state dinners in foreign countries. Once I accidentally packed a pair of peep-toe shoes on AF1 when we were heading to Saudi Arabia, and everyone made fun of me because I was afraid I would cause an international incident when meeting the king. (You’re not supposed to expose your feet.) It wasn’t the end of the world, but it wasn’t awesome. After being introduced to the packing list, I endured far fewer mishaps.

  Also, I never have fewer than two tampons in my bag—one for me, one for a friend.

  (5) On studying: The first lady was particularly adamant about state dinners: They were not just a fancy spread with free food and nice booze; they were work, and you were supposed to show up. Part of knowing how to be prepared comes from being self-aware—being able to anticipate what you’ll need (or screw up) and planning accordingly. I know I am rarely, if ever, the smartest person in the room. And that’s totally OK. What’s not OK is (1) not recognizing that and (2) not coming ready to participate in a meaningful way.

  At state dinners, this meant knowing who you were sitting next to and reading up on a few things to talk to them about. Sometimes, this is awkward; at a state dinner for China, I was next to the commerce secretary, and although I’d looked him up online, there wasn’t a lot of information available. Finally, I dipped into my well of go-to conversation starters, and since there was a musical performance at this dinner, I asked him what his favorite American song was.

  Dey’s Packing Checklist

  Home Checklist

  Clean bathroom

  Clean kitchen

&nbs
p; Clean bedroom

  Clean living room

  Email flight confirmations to AM

  Before Leaving

  Yellow card updated with shots

  Credit cards

  Charge camera

  Purchase Ziploc bags

  Withdraw cash

  Medication

  Band-Aids

  Pain reliever/Advil

  Allergy medicine

  Bug spray

  Sunscreen

  Personal hygiene items

  Toiletries

  Hair ties and bands

  Comb and brush

  Toothbrush (and the case)

  Toothpaste

  Dental floss

  Shampoo

  Conditioner

  Protective UV

  Mouthwash

  Frizz Ease Hair Serum

  Hair wrap

  Flat iron

  Curling iron

  Shower cap

  Dove soap

  Soap holder

  Razor

  Face cleanser

  Makeup remover

  Cotton pads

  Makeup

  Concealer

  Urban Decay Potion #9

  Photo finish

  Eyeliner

  Mascara

  Eyelash curler

  Eyebrow brush

  Eyebrow shadow

  Neutral shadows

  Powder

  Powder brush

  Pink Bobbi Brown blush

  NARS bronzer

  Silver lip gloss and neutral bronzer

  Tweezers

  False eyelashes

  Other Clothes

  Nike Dri-Fit pants

  Black-and-white workout pants

  2 workout tank tops

  Gray sweatpants

  1 tank top to sleep in

  1 pair of shorts

  7 pairs of socks

  Black sports bra

  White sports bra