West Winging It

An Un-presidential Memoir

Pat Cunnane

• Publisher: Gallery Books
• Year: 2018
• eBook ISBN: 9781501178313
• Topic: Politics & International Relations
• Subtopic: Social Science Biographies
• Index: Politics & International Relations

The West Wing meets The Office in this "funny, moving story about working in the White House that is a must read for anyone who misses having Barack Obama as President" (Dan Pfeiffer, cohost of Pod Save America), directly from his senior writer and former Deputy Director of Messaging. West Winging It is the "fitfully funny…warm and observant" ( Kirkus ) story of Pat Cunnane and his journey from outsider to insider—from his dreary job at a warehouse to his dream job at the White House. Pat pulls the drapes back on the most famous and exclusive building in the United States, telling the story of the real West Wing with compelling and quirky portraits of the people who populate the place, from the President to the press corps. Pat takes you into the Oval Office, providing a "snappy, sunny" ( USA TODAY ) insider's glimpse of what it's really like—from the minutiae to the momentous—to work at 1600 Pennsylvania Avenue.Along the way, Pat draws an intimate portrait of the side of President Obama that few were privy to—the funnyman, the nerd, the athlete, the caring parent. He describes both the small details—the time he watched in horror as the President reached over the sneeze guard at Chipotle—and the larger, historic moments, such as watching the President handle the news of the 2015 terrorist attacks in Paris. In some ways, working at the White House is a lot like every office, and in some ways, it's like no office ever. Pat recounts the time he accidentally slammed a door on Joe Biden, plotted to have the Pope bless him by faking a sneeze, and almost killed America's First Dog." West Winging It is a fun, poignant reminder that the best part about working in the Obama White House was the people working with you, and knowing that everyone was there for the right reason: to try to do as much good, for as many people, as we possibly could" (Jay Carney, former press secretary). At its core, it's a fish-out-of-water story—only these fish are trying to run the United States of America.

1

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Warehouse to the White House

Nobody knows really what they’re doing, and there’s two ways to go with that information. One is to be afraid and the other is to be liberated.

—CONAN O’BRIEN

My parents walked me to my first day at the White House.

I know how absurd that sounds and, yes, how ridiculous it was. But they were excited. And I was nervous. It was just four years before, in 2006, that they had traveled with me to my first day of college. What business did I have at the White House? I was out of my depth. Beyond a knack for writing, I had few skills that would translate to success at the White House: a tenuous grasp of technology, a limited understanding of government. I had never used Microsoft Outlook. Hell, I didn’t even know how to make coffee.

My nerves faded for a moment at the back entrance to the Eisenhower Executive Office Building (EEOB), with my parents looking on from beyond the black wrought iron gate below. I was distracted by the remarkable, imposing EEOB—a French-inspired building constructed over the course of almost two decades in the late nineteenth century—which originally housed the Departments of State, War, and the Navy. In 2010, 122 years later, I learned that it was home to the majority of White House offices. As I ascended the stairs, American flags flying overhead, something stirred inside of me—swelling with each step.

You would think it was patriotism, right? Wrong. My twenty-two-year-old self was a bit irked. I had applied for a White House internship, not an Eisenhower Building internship. Plus, Mark Twain once called the structure “the ugliest building in the country.” And I kind of agreed.

Of course, I hadn’t been scammed, I was just ignorant. The EEOB is made up of hundreds of offices, from communications, press, and domestic policy, to legal counsel, correspondence, and foreign affairs. It includes the vice president’s ceremonial office, as well as numerous secure rooms called Sensitive Compartmented Information Facilities—SCIFs, for short. After the assassination of President John F. Kennedy in 1963, President Lyndon Johnson continued to work out of the EEOB as a sign of respect for his fallen predecessor. Roosevelts, plural, had worked there. Wars were planned there. The EEOB is where much of America’s business gets done, for better or worse. My office was across the hall from the room in which Richard Nixon recorded many of his fateful tapes during the Watergate crisis that ultimately brought down his presidency. In 2010, I didn’t have a handle on the history. The place, and the president for whom I was working, were still abstractions to me. I failed to appropriately value the vaunted halls that I rushed through.

Room 181, like most of the offices in the building, featured huge windows, soaring ceilings, and staffers at regal, dark wooden desks. I was situated next to three such staffers, none of whom was thrilled to have an intern stationed so close to them. They were nice, of course, but busy responding to reporters from across the country:

“POTUS has taken into account those figures.”

“Sure, we can get you that as soon as POTUS returns from OMB.”

It sounded like gibberish to me. I was listening to someone’s call, trying to glean something—anything—but it was almost impossible. I overheard: “He’s the OPE POC for LGBT and AAPI issues for POTUS.”^I They were speaking a different language. I did my best to hide my confusion.

My primary goal was to stay out of their way on day one—to make a good, quiet impression.

Following the rush of morning news and journalists’ queries, room 181 fell into what I would learn was a rare silence, interrupted only by sudden bursts of desktop typing or a fit of coughing. We were in an early-afternoon lull, the silence seeming to grow by the minute. I thought about saying something—we’d all exchanged pleasantries in the morning, but I hadn’t said a word in almost an hour. It was an opportunity to showcase my personality, maybe make a joke or bring up some popular movie. I thought about it a bit more and decided against speaking. Instead, I planned to jump into the conversation once somebody else piped up.

Unfortunately, it was my computer that piped up before I had the chance. A pop-up advertisement overtook my ancient desktop. The speaker had been set to booming, and the words rang out crisp and clear:

“Hey, everybody, I’m Justin Bieber!”

Every staffer in the room turned to me. The words echoed off the towering ceiling, reverberating through the room. I maintained my back to my new office mates but could feel their glares piercing my thin façade of competence. I scrambled for the mute button. Couldn’t find it. Bieber kept going.

“Catch me at the Verizon Center!”

After singing about tickets being on sale, Bieber literally began busting moves on my desktop, dancing on my dignity. My hands were shaking on the mouse, and I couldn’t locate the X that’s usually in the top right corner of the browser. Unfortunately for me, this was one of those crafty ads with the hidden Close Out buttons. I did the only tech-savvy thing in my repertoire and punched control-Alt-delete into the keyboard.

Mercifully, I had an excuse to leave, avoiding eye contact all the way out the door. It was time for my security briefing in the South Court Auditorium on the ground floor. On my way into the auditorium, which looked like an Intro to Communications college lecture hall, I got my first glimpse of the West Wing from inside the gates. I watched as a couple of generals exited their black, armored Chevy Suburban SUV and scurried into the basement entrance of the West Wing—presumably toward the Situation Room, which would be immediately to their right as they walked in. Of course, I didn’t know any of that at the time and wondered what it must be like in there. The West Wing. Wow, I thought. I guess this really is a White House internship.

Still, I was too preoccupied with the Justin Bieber disaster to let the moment sink in. What did they think of me in 181? What were they saying?

Our security briefing began with a spot of tough love. A Secret Service agent took the room by surprise: “Congratulations,” he said. “You’re sitting in the cherry on top of every terrorist’s dream cake.”

He was about as subtle as my nana.

• • •

“I was baptized a Democrat, not a Catholic.”

That’s what my nana wanted everybody to know. Whether she was strolling out of St. Luke’s Church, her local parish, with the monsignor or, more likely, sparring with a neighbor or grandson, you needed to know—above all—Joan Cunnane was a Democrat.

The only thing Nana likes more than talking about politics is arguing about politics. When she thought your point was particularly useless, or your argument unsound, she’d give a quick huff, smile to herself, and then look up from the tattered playing cards splayed across her gray laminate countertop. When Nana took her attention away from her never-ending game of solitaire and peered at you through the smoky haze of her 1980s-era kitchen, you knew she had you dead to rights.

And when she held a beat before speaking, shuffled over to the stove, and cranked the burner to ignite her cigarette, you knew she was about to light you up. Now, if she turned down the ever-present drone of MSNBC—God forbid—just to be sure you could hear her argument, well, we grandkids learned to run.

Nana is not known for subtlety. She once proudly ended a fifty-three-year friendship with her beloved Hazel upon learning that her longtime neighbor was sympathetic to Sarah Palin. I watched her say “Goodbye, Hazel” from her kitchen counter. Never spoke with her again.

However, Nana is known for playing favorites, something I’ve benefited from since day one. The morning I was born—November 22—was the twenty-fourth anniversary of President Kennedy’s assassination. Upon picking me up for the first time in the hospital room, she exclaimed:

“I got my JFK back!”

My mother, Madeleine Cunnane, was reeling from a labor that had lasted twenty-two hours. I was big and overdue and unwieldy. I required a suction machine as well as, eventually, forceps, which—when he finally pried me free—sent the doctor flying across the room. I was bruised and my head a little misshapen temporarily from the forceps. Still, Nana saw only a little Kennedy. My mom wasn’t feeling Camelot and found the comment ludicrous. In fact, she rolled her eyes so far into the back of her head that there was some worry the doctor would be needed to retrieve them. She looked over to my father for affirmation that what his mother, Joanie, had said was outright bizarre.

But my dad—my nana’s favorite son—didn’t notice. He was blinded with excitement. The moment he saw my eyes open, he screeched, “Oh my God! He’s a genius!”

Turns out my dad, P. J. Cunnane, lived the first twenty-nine years of his life under the impression that human babies—like kittens—spend the first few weeks after birth with their eyes closed. He thought that I, his firstborn, eyes wide open in minutes, was enlightened. He would learn quickly that he was wrong.

I thought about how off base my dad’s prediction had been as the Secret Service agent who reminded me of my nana droned on about safety. At that moment, my first day, I couldn’t be bothered by bombs and wasn’t worried about weapons. My reputation was already shot, and all I could think about was how to revive it.

When I returned to the office, I considered telling a self-deprecating joke but figured not landing it was too risky. I was already on thin ice with hot blades—better to build back slow. My plan: ask an informed question. I would prove that I was engaged; that I cared about what was going on around me. There was a term that had thrown me off all day. I didn’t know if it was an obscure department or a piece of legislation or what. Sure, I could have googled it, but then nobody would know that I was a serious person here to learn and to do a good job.

But who to ask? There was Steve. He sat in the corner and had a proclivity for reacting—laughing, groaning, bemoaning—to whatever came across his computer screen. I could already tell that the obvious intention there was for somebody to ask him what was up. He was a prompter. Then, as soon as someone inevitably played his or her part and inquired, he would take to reading the entire article word for word. A few interminable minutes later, somebody would eventually say “Crazy,” and somebody else might add “Interesting.” Only then would everybody be able to get back to work. I wasn’t going to ask Steve.

Dylan was another option. He sat an office over. I would come to know that he took his job so seriously that it was hard at first to get more than a one- or two-word answer out of him if it wasn’t mission critical. I’d been warned early on that he also tended to internalize anything negative said about President Obama, letting it build up until he exploded at five in the afternoon with an inventive, impressive, expletive-laced tirade aimed at whomever had most recently taken an unfair shot at his boss. Dylan, however dedicated to the cause, wasn’t right for the question either.

Then there was Matt: a longtime aide who joined the campaign early and took on key roles at a very young age. I didn’t know much about him other than the fact that he had good hair—and he wasn’t too much older than I was, which surprised me given that he seemed to have a vital job. In fact, I was beginning to learn that a lot of young people had important jobs. Despite some heavy typing and aggravated huffs now and then, Matt seemed the most approachable. Like, maybe we could one day be friends. I figured we might have something in common. And when I heard him talking about basketball, I knew he was the right choice. So I geared up for my question, clearing my throat. It was time to create a new narrative for myself in the office.

“Hey, Matt.”

He looked up from his screen and swiveled his chair to me. I took a breath, remembering that there’s no such thing as a stupid question, and proceeded confidently:

“What’s a POTUS?”

I had created a new narrative for myself, all right. I knew from the way the room reacted—even before Matt answered—that stupid questions do, in fact, exist.

“President of the United States, Pat.”

I wanted to get as far away from the White House as possible, to leave the city entirely. I felt like running back to my parents’ hotel. I thought maybe my first instincts about living in DC—not to—had been correct.

• • •

In May of my senior year of high school, I was enrolled—nonrefundable deposits and all—at two universities. A couple things about this: one, pretty sure it’s against the rules; two, it’s definitely a colossal waste of money. Still, maybe I could have gotten around those roadblocks and attended both schools—if not for the fact that they were separated by more than a thousand miles.

Back then, it seemed my mom and I were even further apart, at least metaphorically. We couldn’t agree. I had been accepted early to Georgetown University. My parents were ecstatic, as they were about all things related to Washington. They had a thing for DC—were infatuated, even—and wanted desperately for my two brothers and me to be, too. My mom was adamant that I seize the opportunity presented to me by Georgetown, but my heart was set on the University of Miami. The choice was even clearer after my back-to-back campus visits: the lush, palm-tree-lined entrance to the University of Miami, juxtaposed with the winter drear of Georgetown’s Gothic, gray buildings; the campus pool at UM, contrasted with the campus graveyard at Georgetown.

It didn’t hurt that my girlfriend, Stephanie, was headed with her twin sister, Victoria, to Miami. Stephanie and I had met in second grade. I developed a crush quickly—okay, instantly—but kept quiet. It was a slow burn. For years, I kept up the crush, captivated by her from afar. Popular, but not one of the popular girls, Stephanie was the quiet, beautiful brunette. And in seventh grade, five years after I had first laid my prepubescent eyes on her, I got word she might be interested in me. Our mutual friends literally pushed us together outside the library. Finally face-to-face, I asked, “Will you be my girlfriend?”

Six years into my relationship with Stephanie, my mom and I were three months into a battle of wills about my school choice; if the past was any precedent, my chances of outlasting Madeleine Cunnane weren’t good. Harry, my middle brother, is testament to that.

When Harry was a sophomore in high school at St. Joseph’s Preparatory, in Philadelphia, he decided—against the wishes of my parents and his better sense—to get a substantial tattoo on his side, just below his armpit. Standard fare for a first tattoo: something about “Living today” and “dying tomorrow.” And a cross. I caught wind of it through Facebook and ratted him out—but just to my dad, who I knew wouldn’t much care. Nevertheless, my mom found out (Harry, I swear it wasn’t me) and devised a plan.

She took a blue Bic pen to her right foot and wrote in elegant cursive, “De La Salle”: an ode to La Salle University—where she taught rhetoric and writing—and to St. Jean-Baptiste de La Salle, the patron saint of teachers.

Knowing the reality, the permanence, of his decision, my mom concluded that she wanted Harry to want to tell of his tattoo. So, following one in a series of what she liked to call “come to Jesus” meetings with Harry, she said, “Okay, Harry, I have something to show you.”

And with that, my mom took off her shoe and sock, fully expecting Harry to see right through her farce. Maybe it had something to do with the dim lighting of the den, but Harry didn’t question the authenticity of the “tattoo” on my mom’s foot. He was just shocked—and impressed!—that his professor of a mother had inked up. In fact, he pulled off his shirt, revealing a tattoo the size of a football. More than that, he opened right up to her, telling the story of his own tattoo and asking where my mom went for hers and how much she paid. My mom, not knowing the first thing about tats, told him she went to a nice place out in Bucks County and paid $400.

“Ah, you got cheated!” Harry exclaimed, e...

Table of contents

• Cover
• Dedication
• Cast of Characters
• Prologue: The Beginning . . .
• 1: Warehouse to the White House
• 2: In the Buffer
• 3: Lower Press
• 4: 2012
• 5: Office Politics
• 6: Disaster Casual
• 7: The Normals
• 8: Interviews About Nothing
• 9: Friday the Thirteenth
• Epilogue: . . . Of the End
• Photographs
• Acknowledgments
• About the Author
• Copyright