West Winging It

by Pat Cunnane

  At the request of—okay, maybe with the approval of—one of my bosses, Jen Psaki, I started my mornings later than Andrew, something that didn’t sit well with many in the West Wing who were used to the clips pouring in around five o’clock. Mornings were stressful. I darted into the office, always feeling behind already, anxious every second I wasn’t sending a clip. But once I got out the first dozen news items, I hit a rhythm and got one to two per minute to the team. Only then did I feel that the day was under way.

  For security reasons, the White House complex would restart all of our computers every few days. I dreaded the weekly reboot. Because they were essentially antiques, and due to the sophisticated security measures taken, our computers often took twelve to fifteen minutes to restart fully. And I couldn’t plan to wake up earlier that one day each week, because they often varied the reboot day. So there I would be—sitting in front of a loading screen—getting no credit whatsoever for being at work. Would Axelrod or Pfeiffer or Jarrett think I was slacking off?

  After all, I just wanted people to think I was doing a decent job—and I had no intention to go back from where I’d come.

  • • •

  “Good work, Pat-rick. Really nice, Pat-rick.”

  I nodded, smiled at the recognition of my work, and finished pushing the box of plaid princess line jumpers across the concrete floor.

  During summer break from the University of Miami, I took a job in a warehouse owned by my parents’ close friend and our next-door neighbor, Sean, whose office in Northeast Philadelphia was on the same road as my dad’s bicycle warehouse. I had worked at my dad’s place the summer before, so a second warehouse gig made sense. I was an experienced bike-box mover; how much harder could school uniforms be?

  Apparently, it was a snap, given that Caroline, my supervisor, was heaping accolades on me right from the jump. Caroline was a pleasant, middle-aged woman who regularly wore company products: school sweaters, khakis, plaid skirts, the works. She was seriously impressed with my abilities and seemingly wanted to be crystal clear in her compliments. She kept using my name—my full first name—even when it was just the two of us in the room.

  “That’s perfect, Pat-rick,” she said as I slid the last of the morning’s boxes into place and prepared for an outdoor lunch in the sunshine of a warm June afternoon. Contented with a job well done, I found a shaded spot below the lone tree off the corner of the parking lot, took a seat Indian-style in the grass, and ate alone in silence.

  Sean, a successful, sarcastic man with a penchant for pranks, caught a glimpse of me as he walked to his car. My first memory of Sean, who had become a very close family friend, was “Mischief Night” many years earlier. He arrived at our house decked out in black, clutching a gasoline-powered leaf blower with a special gizmo attachment that held a roll of toilet paper in order to get maximum height and coverage while TP’ing an unsuspecting neighbor’s trees or house. For those who didn’t grow up in the Northeast, Mischief Night is the evening before Halloween when young people—in my case, supported by older people like Sean and my dad—went out and did dumb things.

  Sean waved to me as I finished my sandwich under the tree. I returned the friendly gesture from my seated place in the grass, and he shouted across the lot:

  “You look like a dim-witted Buddha!”

  If only he understood how well I was doing inside. I knew as soon as Caroline reported back to Sean, he’d have to eat his words. Dim-witted? Yeah, right!

  I largely kept to myself the rest of my first week, put my head down and did the work, determined to keep impressing Caroline one box at a time. Finally, on Friday morning, I thought it was time to shove my success in Sean’s face. I burst into his corner office and provided an update.

  “Caroline has been pretty positive so far. I could be looking at a promotion really quick.”

  “Is that right?” Sean asked, propping his feet up on his desk.

  “Just don’t get too comfortable in this office; that’s all I’m saying.” Then I attempted to pull off that quick double-knock-on-the-door thing as I departed, but it didn’t quite work; and I lingered a second too long after the double knock.

  Sean stared at me. “Why are you knocking?”

  “No, I was just trying to—it was like a see-you-later type thing.”

  Despite the stumble in Sean’s office, my success continued that afternoon with Caroline. She kept up her flattery, as well as her overuse and painful overpronunciation of my name. Eventually I took a break in the back of the warehouse in the middle of that Friday afternoon. The cavernous room was silent but for the hiss of the industrial lighting overhead. Suddenly that hiss was punctuated by a familiar sound: flip-flops thumping against the floor. Sean was en route, getting closer. Walking with Caroline, he approached with a smile.

  “So, Caroline—end of week one—how’s he doing?”

  Caroline’s eyes lit up. “You would be amazed, Sean!”

  I was safe. Who’s the dim-witted Buddha now? I asked myself smugly. She continued:

  “Patrick’s doing as well as anybody else here. He’s fitting in and keeping up and—”

  “Caroline, let me stop you right there,” Sean, in his gravelly voice, interjected with a smirk. “Pat’s not actually intellectually challenged.”

  My jaw nearly hit the concrete floor. Caroline was mortified. Sean had told the staff to watch after me, that I was “special.” It was a con that had lasted five days. I had no idea what I would do next, but I knew I needed to get out of the warehouse and find a place where I wasn’t the punch line to everybody’s jokes.

  • • •

  At the White House, a few months in, I finally felt like I was getting the hang of things. By then, Andrew had been promoted. I had developed a routine and was beginning to get a sense for the way the news worked. What interested people, what mattered, what didn’t. And sometimes, most importantly, what shouldn’t have mattered but would likely catch fire online. That was the rapid-response part of the job, sniffing out future problems, regardless of how inane, and getting them in front of the staffers best equipped to handle them.

  Often, that staffer was my boss, Dan Pfeiffer, one of President Obama’s most trusted advisors. Ultimately, Dan was responsible for dealing with anything said about the president—online, in print, or on TV—which made him very invested in the media monitor. Dan had served as an intern in the Clinton administration, and, when I started, was the White House communications director. As monitor, I saw him only for short gusts when he would burst into the offices of the EEOB, making his rounds to visit the staff that didn’t sit in the West Wing. He was typically funny, clearly very smart, and seemed to switch from socially awkward to the witty life of the party with ease. He always had a take on the topic of the day, and it was usually better than yours. Ultimately, Dan was the archetype “Obama guy.” Hardworking to the point of physical consequences, Dan rose at four in the morning and eventually had a ministroke at a dinner with reporters. (He’s fine.) Like his boss, the president, he loved basketball, hip-hop, being right, and electoral politics.

  I didn’t know any of that initially. In those early days, I remember Dan mostly for walking swiftly, just ahead of a staff assistant, Jimmy, who dripped of competence and meticulousness. Like most assistants at the White House, Jimmy helped run his principal’s life at the expense of his own. Jimmy was dedicated, determined, and—I would learn—in need of a new gig.

  Dan was constantly clutching a rectangular white notecard with “White House” written in regal blue lettering at the top. Jimmy used to review the card often. I would come to know that those cards, usually filled with a dozen or more meetings he needed to attend that day, were highly coveted over in the West Wing. Staffers scrambled to get their hands on them—status symbols, really—hoping to jot their to-do lists on the matte-finish cards rather than on the smudge-inducing glossy cards. I’d learn the difference later. For now, my focus was on my computer. The news.

  One of th
e more common DC news cycles—and a personal favorite of mine—went like this: newsworthy event is reported on; reported event is reacted to by pundits and columnists; reaction to reported event is reported on and reacted to by other pundits and columnists.

  A few years before I started, this cycle could have taken a week to play itself out. In fact, the head of the White House Research Department, Ben, used to tell stories of his time as a media monitor in Washington. This was before the internet took hold. As he told it, he would be up through the night, literally cutting out (you know, with scissors) headlines and stories from newspapers, gluing them together, copying them, and leaving stacks on his coworkers’ desks before dawn. When he would tell these archaic tales, I imagined him in an old-timey plaid hat with the tiny brim that grandpas like to wear, ink splashed across a pair of worn overalls. The guy is only ten years older than I am, but in the age of Twitter, it felt like there was an eternity between us. You see, while that usual cycle—event, reaction, reaction to reaction—would take days just a few years before, now, thanks to Twitter, it cycles through in just a few hours. Over and over. Every day. No wonder Andrew was hospitalized.

  The job was already beginning to wear on me when I learned that the FBI still hadn’t even concluded my background check. In late March, I got a call from Sean, who relayed to me that he had just been interviewed. He said the agent asked several questions about my girlfriend’s family, but other than that, the conversation was straightforward. Stephanie’s family is Italian American. They retired early following the sale of their successful, eponymous family business: a supermarket chain called Genuardi’s. Sean assured me that the investigator’s questions were likely nothing—completely standard—and that the rest of the interview went very well. In truth, I was thrilled that the FBI had interviewed him; that my position was consequential enough to merit federal investigation. It was the ultimate revenge for his prank in the warehouse, I thought.

  A couple days later, just as I sent out the last of the morning clips, Stephanie called.

  “Pat! They’re here with guns, the FBI! They’re searching my parents’ house.”

  I exploded out of my seat and rushed into the hallway as Stephanie continued, frantic: “They keep talking about the Mob. I don’t know what to do!”

  I was shaking. This couldn’t be right. But I knew that the FBI had been asking questions a few days before, poking around. I didn’t have any answers for Stephanie but promised to get to the bottom of it. I hung up, knowing no recourse. I told one of my supervisors what was going on. I needed to be away from my desk for a little bit. There would be no clips for a few minutes. I had some news of my own to deal with. My supervisor, shocked, told me to keep her posted. I realized who I needed to call.

  Sean picked up on the first ring. “What exactly did the FBI ask you about the Genuardis?” I demanded.

  “I’m not sure. I don’t think it was anything too serious,” he responded.

  “Well, it is serious!” I yelled. “They have guns!”

  “Pat, Pat, Pat.” He tried to calm me down, but I was panicking. “Hold on a second.” Then he seemed to click me onto speakerphone. I could hear commotion on his end. His next sentence came out clearly:

  “Look at the calendar, jackass.”

  I pulled the phone from my cheek and waited for the screen to illuminate. The dateline gave it away. Stephanie was in on it.

  April 1, 2011.

  My coworkers had seen me fretting, frantically pacing the hall outside our office, shouting into the phone. All for nothing, a joke. It was my biggest embarrassment since asking Matt what a POTUS was shortly after blaring Justin Bieber throughout the office, and I was frustrated with myself for falling for another Sean prank. I should have had my guard up on April Fools’ Day. I was more determined than ever to prove myself a competent, if not good, media monitor. So when the summer of 2011 rolled around, I seized the opportunity to work late; to contribute in a time of supposed crisis.

  Washington was mired in the debt ceiling debacle of 2011. For years, raising the debt ceiling had been routine, immune from partisan negotiations. But Republicans had taken back the House the year prior and were intent on upending those economic and political norms. I was told to send every tweet, no matter how seemingly mundane or tangentially related to the debt ceiling debate. The White House needed its most precious commodity: information.

  I think Dan had Andrew’s hospitalization in mind when he emailed me one night around midnight, telling me to stop sending clips—individual tweets, really—for the night and to get some sleep. I was proud to be a part of the team and grateful to get an email from the boss, but the high of feeling like I was contributing wore off quickly from my perch in the EEOB. It became tiresome, stuck sending endless tweets. It was hard to comprehend that what I did mattered when my job was so straightforward: copy-paste-send. It didn’t feel entirely different from moving boxes in a warehouse.

  Worst of all, most of the tweets said the same thing—namely, nothing—about an opaque partisan dispute that I was sure would work itself out just like every other manufactured Washington crisis. I didn’t know that in the West Wing, they weren’t so confident that things would be okay.

  Obama would say years later, in his last official interview as president (coincidentally enough, with Dan on his popular White House podcast Pod Save America), that this was one of the most frightening, frustrating periods of his presidency. “It was a very realistic possibility,” he said, “that we would be in a situation where technically we were in default—in uncharted territory.” The votes didn’t seem to be there among Republicans to avoid defaulting on the debts of the United States. Jon Favreau, Obama’s chief speechwriter for the entire first term, had begun drafting the speech should it happen. Just across the driveway. To Obama, it was the scariest moment of his presidency.

  To me, on the other side of West Executive Avenue, directly across from the West Wing, it was hard to get a sense of the gravity. It could be isolating in the EEOB—especially for the media monitor, given that you are essentially tethered to your desk from the moment you enter the building to the minute you race home. It was as if I were watching my favorite show for fifteen hours every day—Seinfeld, for instance—only to be reminded periodically that my office was on set, and that the misadventures of Jerry, George, Elaine, and Kramer were taking place all around me every day. I couldn’t help feeling like I was some sort of odd mixture—caught between staffer and spectator—as tangential as the tweets I was sending every fifty-five seconds.

  On the other hand, many of the EEOB’s employees crossed West Exec multiple times a day to check in with the West Wing. That’s where you could truly get a sense of how grim things had become. You could measure the depth of concern by the number of closed doors. Such was the scenario in 2011, even if I couldn’t sense it from my computer station. Truth be told, I hadn’t even seen the president in the six months since I was an intern. But I did what I was told, kept plugging away, clip by clip.

  It was during this period that I bumped into Dan while departing the West Wing one night around nine o’clock. I was walking my Fuji bicycle along West Exec, ready to dash down Pennsylvania Avenue toward my apartment near the Capitol, about a fifteen-minute ride, where last night’s Domino’s pizza was a perfect twenty-two-hours cold. Dan and I made small talk. I didn’t think much of it, but I would learn that I made an impression.

  A few days later—as I hit my nadir—the White House posted the salaries of all administration employees online. Seven months after the New York Times had written glowingly, and deservedly, of my predecessor, the Atlantic took an interest in the unique position as well; only this time, I was at the helm, and its take was slightly different than that of the Gray Lady’s. The magazine posted a blaring, bold headline that read: “White House Posts Salaries: What’s a Media Monitor?” Then, jokingly, it accused the White House of burying this news on a Friday afternoon because we “wanted to give the press the smallest possi
ble window of opportunity for follow-up questions about the White House media monitor, what he does, and why he makes $42,000 a year.” You’ll note that $42,000 was the minimum salary for the Communications Office at the White House.

  It was an embarrassing article, but, hell, at least it was a bit of recognition, which certainly didn’t bother me. The thing that did bother me? I wasn’t the one to catch the news clip.

  Andrew had sent it to me.

  That’s when I realized I’d never live up to the standard set by my predecessor. It wasn’t even his job anymore, and he was still outmonitoring me. I couldn’t imagine getting to the point where I’d media monitor myself right into the hospital. And that’s what you needed to thrive in the position. My successor, Hannah, had it. Before she was promoted, she did a stint in a cast, her wrist undone by excessive copying and pasting, the repetitive pinky-index action of the CTR+C, CTRL+V. Talent, motivation, enthusiasm. Something was missing for me. I was beginning to long for my days in the warehouse. The sense of accomplishment, of moving hundreds of boxes from one place to another, the ability to see and touch your progress. Looking at my Sent email box didn’t provide the same level of pride. Media monitoring, though a fantastic experience and one I am grateful for to this day, never came naturally to me. I wasn’t good at it.

  Fortunately, sometimes at the White House, you fail up.

  Unbeknownst to me, Dan had laid the groundwork for me to move on shortly after our encounter that night on West Exec.

  “Pat looks like death,” he told his deputy the next morning. “We need to find him a new job.”

  And so the process of finding me a new position began. The Obama White House, vaunted for many reasons, was not known internally for having a highly functional human resources department—at least in the early years. The typical next step for a media monitor is to researcher, or press assistant, or if you’re lucky, press wrangler, which meant sitting on the front lines in the West Wing and—incomprehensible to me at that time—traveling with the president. I barely spoke about it with friends or family, too worried that I might jinx something; that my bosses would realize that I had no business in the West Wing. Were they truly going to pull me away from my corner in the EEOB and put me right on set? Didn’t anybody realize I was an imposter?