West Winging It Read online

  You see, I didn’t start out working for him in Chicago. I wasn’t indoctrinated into Obama World from the start. I wasn’t around during his days in Springfield, the capital of Illinois, or in the United States Senate, or even on the 2008 campaign—so I wasn’t introduced to Barack Obama the state senator or Barack Obama the US senator. I came to know of Barack Obama the same way the rest of the world did. From thousands of miles away. As the most famous man in the world.

  • • •

  My nana knew the name Barack Obama before I did.

  She was on to his charm, hopeful for his vision, even as I was just trying to get through high school and then college.

  Of course, as the 2008 Democratic presidential primaries ramped up, I saw the crowds grow by the day. I watched the nightly news slowly begin to take him more seriously; this upstart underdog from the South Side by way of Hawaii and Indonesia. Yes, I remember where I was when he delivered his first famous convention speech (Cape May, New Jersey) and what I felt—my first flicker of real interest in politics—as he laid out his belief that there are better days ahead. (“Why can’t this dude be president?”) But beyond those seventeen minutes in July 2004, I didn’t think of him until 2007—I was nineteen—when my nana turned down the volume on MSNBC and asked me a question.

  “What do you think of Barack?”

  I hadn’t yet given the upcoming election much thought, but Nana wasn’t waiting for me to answer. She tapped her cigarette in her ashtray and told me the way it was going to be.

  “Barack is going to be president. I love him. I consider him my son.”

  • • •

  I don’t remember well my interviews for the press wrangler position. I know I was nervous to meet the new press secretary. After all, I knew Jay Carney only as the Jay Carney from TV. I hadn’t dealt with famous, or at least DC-famous, people in the EEOB, and certainly wasn’t prepared to be interviewed by one for a job. Hell, I was nervous just walking into the West Wing. It’s not something I pictured when Barack Obama caught my attention in 2004, and certainly not what I anticipated for myself when my nana told me about her new “son.”

  Still, my luck rolled along. All of the conversations were fairly pro forma; I had the inside track on the position. And I got it.

  After word had spread that I was moving, I returned to my desk in the EEOB to find a package of stickers: Justin Bieber collectibles. It was a lighthearted jab that made me feel like I was a part of the team; that maybe I had finally broken into Obama World. This was a shot of confidence I would need as I made my way to the West Wing for the first time, a place I would spend more time over the next five years than any apartment or condo I would live in. It would become my new home. I had seen the president a number of times as an intern, but nine months as a staffer in the EEOB, and I had yet to cross paths with him. That was about to change in a big way.

  • • •

  First, though, Sean was in town and wanted to take me out to dinner to celebrate my promotion. In DC for a meeting with a local high school about its uniform needs, Sean was unusually sincere on the phone with me, genuinely impressed by the promotion and the move to the West Wing. Dinner would be his treat. He’d pick me up in front of the regal Willard Hotel. It’s said that the term “lobbyist” is derived from the Willard’s lobby, which makes sense given the hotel’s prime location between the Capitol and the White House, just a block or two away.

  I made my way down Pennsylvania Avenue around eight o’clock, waiting on the corner out front of the Willard. I was wearing a dark suit, like usual. A cab lurched to a stop in front of me, and the back door swung open. I slid in next to Sean, already in the back. He shook my hand formally and stated his name, like we were just meeting.

  “Sean. How are you? Patrick, right?”

  I guessed he was finally treating me like an adult—maybe the promotion had something to do with it—so I played along. Shook his hand. “I’m doing well,” I said. “A little tired.”

  “I bet so!” he said. “How’s the West Wing?”

  I was still very much adjusting to the pace of the West Wing, the frenzy of it all. We were halfway down Pennsylvania Avenue, our cab driver clearly speeding. “Ah, you know, it was nuts in there today.”

  The cab driver, shaking his head in disgust, glanced at me in his rearview mirror as he zigged through traffic, making remarkable time.

  Sean asked our driver, “Can you believe this guy works in the West Wing?”

  At this point, our driver became very uncomfortable, wanting nothing to do with me or Sean or the conversation. Unlike basically every other cab driver in the city, apparently, ours didn’t enjoy talking about politics. So I turned to Sean and focused my answers on him.

  “It was a little rough today.”

  Now the cabbie looked horrified. Undeterred, I continued.

  “Everybody was all over me in there.”

  My head jerked forward as the driver threw the car into park; we were out front of another hotel bar, where we would grab some food and a drink to celebrate. Sean helped me out of the cab, which I found unnecessary. As the cab pulled away, I remarked on how disinterested—disgusted really—our driver seemed about the White House. “He must hate Obama or something.”

  Then Sean smiled, and my heart sank. He told me that as the cab was rounding the corner to the Willard, he pointed me out—standing on the corner in my suit—and, right before picking me up, told the driver that he was excited and a little nervous:

  “I’ve never picked up a DC prostitute before.”

  I had gone from the warehouse to the White House, yet I was still the butt of the joke.

  * * *

  I. Translated from White House speak: “He’s the Office of Public Engagement point of contact for LGBT and Asian American and Pacific Islander issues for the president.”

  2

  * * *

  In the Buffer

  We are all on a highway to hell for all of eternity.

  —WOMAN ON MEGAPHONE OUTSIDE THE WHITE HOUSE

  Barack Obama burst into our office. He was pissed.

  I hadn’t seen him like that. Heck, I hadn’t seen him at all—not since I was an intern. To me, he was still the figure—from the news and forthcoming textbooks; from the clips I pulled by the thousands—whom I’d heard about in my nana’s kitchen and from strangers no matter where on Earth I traveled, the very embodiment of the globe’s hope for the future.

  “What in the hell is going on?”

  Jimmy shot out of his seat the instant the president exploded in, grabbing Dan from his office. “Mr. Pfeiffer!” he exclaimed in a kind of whispered screech. Nobody ever called him Mr. Pfeiffer.

  The president was fuming over the ongoing payroll tax cut debate, which had gripped DC. Most pundits agreed that Obama and the Democrats were on the correct side of this one—both in terms of policy, but also, especially, when it came to the optics. Democrats had proposed a tax increase on individuals making more than $1 million per year, while Republicans were allergic to a tax hike on the rich and preferred spending cuts. It was seen—like almost everything between Congress and the White House—as a proxy issue for the next election. Republicans were hesitant to allow POTUS a “win” as the 2012 campaign heated up.

  I didn’t understand any of that when Obama erupted into our humble bull pen. I was brand new to the place. I had only just crossed West Executive Avenue to the West Wing. I half stood, nearly bowed—I hadn’t thought to ask about the proper protocol—and then I noticed that nobody but Jimmy was on his or her feet.

  The West Wing was filled with a new cast of characters for me. Bobby sat in front of me. A former college football player, he was the kind of guy who is exceedingly cool from afar but endearingly nerdy when you get to know him. He had a Clark Kent look—tall, square-jawed, trendy glasses—but his love of cats and photography made him feel more approachable. He volunteered during the 2008 Pennsylvania primary in the Press Office under Matt, who, on his first day, asked
him to write a media advisory. An hour later, he still hadn’t finished, so Matt asked him what was up. Bobby hesitated and then said, “So . . . what’s a media advisory?” It wasn’t quite so bad as me asking Matt what POTUS stood for while already working at the White House, but Bobby had come a long way from that moment.

  Howli sat to my right. She was smart, fun, and—because we started in the West Wing on the same day—sympathetic toward me. A big-sister type. Howli began on the 2008 campaign as an unpaid fellow before graduating to a field organizer in North Carolina. She could talk with equal aplomb about red carpet fashion and issues of voting rights and gerrymandering. She was extremely open—and, whenever possible, I tried to follow her lead.

  She and Bobby were doing their best to keep working even as the president propped his hand on the back of Howli’s computer and laid down the law for Dan and Jay. I followed suit, sliding as quietly as I could back into my seat. Look busy, I thought, as I pulled up a Microsoft Word document and typed a variation on the same fake sentence over and over until the president cooled down.

  He wasn’t screaming. He didn’t need to. He was using his presidential privilege to make a point—raising his voice just a bit. Crystal clear. Message received.

  But to me, his words blurred together, sounding a bit like the adults in a Peanuts cartoon special whenever Charlie Brown is in the room.

  I hadn’t been around him much yet. So far, my first week in the West Wing had been overshadowed by the birth of my first niece, Harry’s daughter Aubrey, up in Philadelphia. Still, I sensed an odd joy in the president’s contained outburst—a glint in his eyes, glad for the opportunity to loosen his tie and vent about Washington. I just hoped desperately that no reporters would amble in at this less than presidential moment.

  As a newly minted press wrangler, I was beginning to learn the ways of the West Wing, the White House press corps, and our little piece of real estate perched between the president and the press. I would spend my tenure in the West Wing here. We called it Upper Press, a small suite of shared desks between the James S. Brady Press Briefing Room and the Oval Office, about thirty feet from each, situated somewhere between historically remarkable and utterly regular.

  There are a series of four Norman Rockwell paintings that hang on the outer wall of Upper Press. Each frame depicts the scene in the White House waiting room—the West Wing lobby—in the early 1940s, when Franklin D. Roosevelt was commander in chief. As you near the Oval Office: newsmen huddle with an administration official; celebrities of the era hope for face time with the president; military leaders prepare their briefings.

  In the fourth and final painting, we see the door to the president crack open.

  Just as Rockwell’s So You Want to See the President illustrates what it’s like on the periphery of power, I was beginning to understand that my own story of proximity and history was just getting started as, for the first time, Millennials helped run the country.

  I was in frame. Sort of. But I had a lot to learn.

  The first thing I gathered was that the reporters who came to the White House each day were free to enter our offices as they pleased. We were a kind of buffer zone between POTUS and the press.

  Now, the official meaning of buffer within the White House is the space between the president’s stage and his audience—typically six to ten feet deep, cordoned off by a bike rack or blue pipe and drape, and built into nearly every presidential event. During my time with the president, the area was filled with the press pool, Secret Service agents—and me. It’s the angle from which photographers can get the “hero shot”: a from-below portrait of a president or candidate speaking from the podium. During his presidential campaign, Donald Trump often did not let reporters into the buffer because he was not comfortable with the way his chin looked when photographed from below. I doubt President Obama had an opinion one way or the other, but we in the Obama Communications Department—the folks tasked with thinking about such matters—loved that angle and photo. We were blessed with a handsome principal, which made our jobs, superficially at least, somewhat easier. So the buffer was important to us.

  And our place in the unofficial buffer of the West Wing was crucial. Just as we encouraged reporters to take up positions by the stage at events and rallies on the road, they often spilled into our workspaces in the West Wing without warning, which is why I was concerned that a journalist would walk in on POTUS as he hammered out his frustrations. To move beyond Upper Press, reporters needed explicit permission, and they required—and rarely received—an escort by a White House staffer. It all added to the complexity of an already bizarre place. The Communications Office and the Press Offices, known as Upper Press and Lower Press, respectively, are situated directly between the president’s office and the press corps’s stomping grounds—equidistant, a sometimes fuzzy zone of its own that I was still getting used to as the president wrapped up his diatribe.

  I noticed Pete Souza, the president’s photographer, snapping photos from down the narrow hall, capturing a few of the countless behind-the-scenes moments for which he would become famous. The best of the bunch were turned into “jumbos”: blown-up photos of President Obama hung throughout the West Wing and the EEOB. They switched them out every two weeks. There was always a new favorite to look at while walking from meeting to meeting.

  Initially, I was alarmed at the president’s visit, but it turned quickly into something else. I felt honored to see Barack Obama this way. Gone was the polished politician smiling in front of an adoring crowd. Vanished was that silhouetted figure waving to a world that viewed him at best as a once-in-a-lifetime leader or at worst as a once-in-a-lifetime orator from Kenya—but most certainly not like he was that day in our office. At that moment, he was just a frustrated guy trying to get stuff done. This wasn’t artist Shepard Fairey’s iconic Hope Obama; this was something better.

  As quick as he came, he was gone.

  The president’s visit set our room abuzz. Jay and Dan scurried into Jay’s office. “I’ll have Josh come up,” Howli said, picking up her phone.

  Josh Earnest was Jay’s principal deputy and almost certainly the next press secretary. He was like everybody’s big brother, widely respected for his great hair, clean jokes, and dedication to the president. Josh always had a sense for how to handle the day’s problem, no matter how big or small. I once had Josh edit a Yelp review I was thinking of posting about my car dealership. I suspect the president counted on him for slightly more pressing topics.

  Josh made his way up in moments and slipped into Jay’s office. As Josh closed the door behind him, Jimmy sat down and exhaled a breath he’d seemingly been holding in for minutes. Bobby let out one of his catchphrases, “Whoa, doggy!” and I closed my Word document. My perception of the president had been altered forever. Turns out I wasn’t working for some sort of rhetorically gifted robot, naïve as that notion may have been in the first place. I was learning that Barack Obama was something else entirely, something far more complicated and much more impressive.

  • • •

  Joe Biden was what you would expect—in the best possible sense. On my very first day in the West Wing, somewhat lost, I watched as the vice president approached from down the narrow hall off the main lobby of the West Wing. I froze, a deer in headlights. Quickly, I turned to get out of his way, scooting through the large, dark wooden door to the lobby. I looked back; he was close now. Biden seemed to almost be saying something, but there was no way he was talking to me. He wasn’t quite near enough that my holding the door wouldn’t have been awkward. Plus, I thought he would be making a left to head down the stairs, not a right into the lobby with me. I continued. The door slammed behind me with a crack that echoed through the lobby.

  On the other side of the door, I heard as clear as day: “What? Am I talking to a door here?”

  I was mortified. I did not want to get on Biden’s bad side. You see, he reminded me a great deal of my own grandfather, my “pop-pop,” who is also a cl
ose talker and seems to know everyone, the de facto mayor no matter where he is. Like the vice president, Pop-Pop likes to grab your arm when he talks to you. Quick with a quip. Ready to route the conversation back to being Irish. Because of these similarities—or more likely in spite of them—Biden was on my nana’s short list of acceptable politicians. In fact, she loved him. Maybe more than my actual pop-pop, her husband.

  So I loved him too. It was hard not to. The vice president had a saying—one among many, but this was his most important—that his mother taught him: “Nobody is better than you, but you’re better than nobody.” From what I saw, he lived that creed every day, from the way he gave the time of day to everybody, no matter his or her status, to the bathroom he chose to use. Sometimes I would end up at the urinal next to him in the West Wing basement lobby bathroom—a four-stall, two-urinal affair with low ceilings and white marble—one level below Upper Press and the Oval Office. Exiting that same bathroom one afternoon, I watched as President Obama, back from a political speech, sauntered down the hall. Suddenly Biden burst into the basement lobby entrance, calling out, “Hey, boss!”

  He darted down the hall to catch him and put his arm on Obama’s back.

  “That was great out there today!”

  “Thanks, Joe. I had fun,” the president responded as they rounded the corner together. This was years before the Obama-Biden memes took the internet by storm, but the veep bounding down the hall after his “boss” was a meme come to life. It was a charming reminder of why people love the guy so much—and why I hated offending him, especially on my first day.