West Winging It

by Pat Cunnane

  After slamming the door in his face, I did the only thing I could think of. I ran back to my half desk in Upper Press and emailed his press secretary to apologize. She said not to worry about it—that I’d get used to things like that.

  • • •

  For an office space no more than thirty feet from the Oval, Upper Press is ordinary, uninspiring, and cramped. Composed of three offices, four desks out in the open, and nine people, things were tight. In the bull-pen area where I sat for five and a half years—I’m proud to say longer than anybody else in the Obama administration—there were four desks, two of which were shared, as well as a bastard of a printer, a fax machine that hadn’t been used in years, and multiple TVs tuned permanently to the quad: a White House station that bombarded us simultaneously with CNN, Fox News, MSNBC, and Bloomberg News.

  I would find that our office fit in with the rest of the West Wing, where square footage hardly squared with the complexity or the prominence of the place. Even as the need for more offices and additional personnel grew over the years, the building’s footprint has remained stubbornly the same. It’s a maze of narrow, “jumbo”-lined windowless hallways connecting understated waiting areas to small offices and overcrowded conference rooms.

  Occasionally, older journalists would meander up our tight hall—taking full advantage of the fact that none of us had doors—and recount what notable people had sat where and when. They particularly liked to remind Howli that she was sitting in Diane Sawyer’s old seat, and that George Stephanopoulos was right here, and Rahm Emanuel over there.

  “I heard John F. Kennedy used to work over there, too,” I wanted to say while pointing toward the Oval.

  The Office of the White House Press Secretary, which is one of the largest in the West Wing, is the exception to the cramped rule, featuring a couch, working fireplace, large desk, table, and chairs, as well as a wall of digital clocks displaying the current times in hotspots across the world, from Cairo to Moscow, to Beijing, to Jerusalem. That’s where we gathered as a group for morning meetings, staff parties, and special occasions such as State of the Union addresses or to watch election returns.

  The deputy communications director and the communications director each had significantly smaller offices, despite the fact that the communications director outranks the press secretary. At first, it was hard for me to tell where everybody ranked; all I knew was that everybody outranked me. Bobby and Matt often asked Dan if they were technically allowed to fire me. His answer normally depended on how the day was going, but “You’re fired, Pat” became a familiar refrain around the West Wing.I

  So Dan was ultimately in charge, but in our world, it made more sense for the press secretary to occupy the bigger office, as he spent his mornings being briefed by between four and eight deputies and assistants such as Amy Brundage, who before becoming a deputy communications director was responsible for press about the economy (no small task in the early days of the Obama administration), and Ned Price, who was in charge of national security press. Matt and Bobby were a part of those prebriefings, too. They would volley mock questions back and forth in preparation for the daily press briefing just down the hall, through Lower Press and past the sliding blue door to the podium in the Press Briefing Room.

  Lower Press was the slightly grungier—though they would say the “tougher”—version of Upper Press. They had three offices, too, but those doors slid; no hinge. In the winter, their heater never worked, and in the summer, mosquitoes loved Lower Press. Those who sat there were beholden to a large, automatic sliding door that opened to another automatic door that swung open to the Colonnade, known mostly for famous photos of American presidents walking with leaders from around the world discussing affairs of state. It’s a grand, stately walkway, befitting the business that gets done on it.

  But when the president departed from or returned to the South Lawn via Marine One, the Colonnade was also the corridor for the fuel fumes that wafted from the helicopter up the Colonnade and into Lower Press, swamping the eight or so staffers in its stench.

  In the past, Lower Press had been described in the media as a kind of frat house—a young men’s club—but by the time I moved over to Upper Press from the EEOB, the gender balance had roughly equaled out in our sister office down the hall. Josh and Amy, two of Jay’s most crucial deputies, had offices there. Matt—the Matt who knew me as the guy who loved Justin Bieber and didn’t know what a POTUS was—had moved in. Marie and Antoinette (yes, these are their real names) sat next to each other as you descended into Lower Press.

  Marie, Antoinette, and I had started as interns and fortuitously made our way over to the West Wing. Antoinette, from the Bronx, was often affectionately referred to as a “wise Latina” and sometimes as a “saucy Latina” by her colleagues. I knew her as the staffer who understood how to work the system. If you needed something accomplished—from better food at the mess to better press for the president—Antoinette wasn’t going to let anything get in the way of getting it done. She ended every day with the nonironic pronouncement “It’s been a pleasure serving the American people with you today.” Marie, the pride of Cranston, Rhode Island, was a whip-smart Duke University graduate with a hummus obsession and a—perhaps related—perennial stomachache. We would become wrangling partners for the 2012 campaign, traveling together on each trip, for every stump speech, “OTR” (on-the-run, or unannounced) stop, or closed-press fund-raiser. She was beloved around the White House and among the press—reporters had to do their best not to groan audibly when they’d learn that I was their minder instead of Marie.

  Jimmy made the quick trip down the ramp from Upper to Lower Press often, because they had the lower-tech printer that was more suitable for reprinting Dan’s ever-evolving schedule card. After POTUS’s visit, Dan’s day was blowing up, and a reprint was in order. Dan and Jimmy shared an archetypal boss-assistant relationship in the West Wing. Like so many West Wing duos, theirs was a bond built on shared anxiety, mutual fear, and—ultimately—friendship.

  Most assistants in the West Wing last roughly eighteen months to two years before they move on. As the third year starts, a psychological wall seems to come down. Frustrations once manifested in hushed whispers and hidden eye rolls come to light through slammed phones and abrupt exits. Scheduling changes are taken as a personal affront, and adjustments made only begrudgingly. For the most part, White House senior staffers did a good job of recognizing the wall and doing right by their assistants: promoting them internally or throwing their considerable weight behind their candidacy for an external gig.

  Dan had seen that I was at that point on West Exec. He used to say often that it was important to take care of the junior staff “to prevent a coup.” It was getting to such a point for Jimmy, too, though he did his best to hide it. Jimmy, who seemed always to have a sense for trajectory, related a story to us once. He was eleven, and upon completing the school year, he approached his subpar teacher—pencil case surely in hand—and said, “The most just thing to come out of this year is the fact that I will move on, and you will stay here.” Suffice it to say, Jimmy was struggling to rein in rampant frustration at this point in his seemingly stagnant tenure. Smart and driven as he was, Jimmy was ready to put his talents to more substantive use than scheduling, no matter how important that scheduling may have been. He tried to cover: he was as chirpy and cheerful on the outside as he was infuriated and foiled on the inside.

  Back from Lower Press, he settled into his seat, largely hidden behind his massive computer screen. Trying to dust off his irritation at yet another reprint, he asked, “How was your weekend?” and began reorienting his mug of razor-sharp pencils. Jimmy never used the No. 2s, but apparently the chief of staff had once said that those with sharpened pencils were to be taken note of. Jimmy had dozens.

  “Oh, it was pretty good, thanks,” I replied without volleying the question back to him. Not because I was rude, but because I already had a pretty good idea of how his weekend had been.r />
  As I delivered my canned response, I teed up an email to some coworkers. The subject line contained only a period, a part of the language in the West Wing. It conveyed that the body of the email was going to be snarky and best not to be opened in front of others. Into the body of the note, I typed:

  “It’s Tuesday.”

  Yes, Jimmy had a habit of continuing to ask how your weekend was well into the week. Late Wednesday afternoon remains his official record. Rumors swirl that the question was posed midmorning on a Thursday once, but that’s something I can neither confirm nor deny. I thought better of sending the note, what with the Presidential Records Act mandating that work emails be stored and eventually released publicly.

  It can be easy, even for the most earnest employee, to forget when chained to a desk fifteen hours per day that said desk occupies some of the most valuable real estate in the world. It happened to me. It happened to everybody. That’s why visits from the president—even when he was pissed—were so vital: they provided a kick in the pants. A reminder of where we were and why.

  • • •

  “Got any snacks?” Pete Souza bellowed from down the hall, camera in hand.

  We always had treats because reporters were constantly dropping them off. They tended to pile up on top of the fax machine that never got used. Cupcakes, donuts, rum cake, cookies, and the like. The holidays were the best—or some would say the worst—when we would be showered with chocolates. The Russian reporter used to bring vodka; one time he brought a bottle with Barack Obama’s face on it. Howli asked if we ought to get it swept for listening devices. Jay, who’d worked as a reporter for Time magazine in Russia, burst out cackling. “Where would they hide a bug in vodka?”

  I laughed thinking of the Russians listening in. This was a few years before we realized just how active the Russians aimed to be at our highest levels of government.

  One of our favorite photographers, Doug, brought his famous pretzels with Hershey’s Kisses baked right in. Word spread quickly through the West Wing when the pretzels were in play.

  “These don’t have nuts, right?” Pete tried to confirm as he grazed through piles of boxes containing chocolates and candies. He popped a piece in his mouth and headed for the hallway. “I love it when he gets fired up like that!” he said with a sly smile, referencing the president’s earlier flare-up.

  As Pete exited, Brian, the director of Oval Office Operations, swung through the door to our office, the one that connects to the hallway outside the Roosevelt Room and the restrooms. Not the one I sometimes shared with the vice president, but the single men’s and women’s restrooms situated midway between the Oval Office and Upper Press.

  Brian, always dressed impeccably, was the unofficial arbiter of style around the West Wing. Officially, he was charged with ensuring that the president’s in-house events ran smoothly and that the decorum—from the Oval Office to the East Room—was upheld.

  “Jesus, who’s been in the men’s room recently?” he called out, swinging the door open like Kramer bursting onto set. “Disgusting!” It was becoming a thing. Brian was determined to root out the West Wing pooper.

  Schultz sauntered in next, grossed out. “I have a flag about the men’s restroom,” he said, which sent Brian sprinting back into the hallway to get a handle on things. A “flag” was something that could become a thing, and a “thing” was code for a “problem.” And when a flag became enough of a thing, there was only one person to call.

  Eric Schultz was the White House fixer. He relished—indeed, encouraged—the inevitable comparisons to Kerry Washington’s character on the TV drama Scandal, the male version of Olivia Pope. Truth is, he was talented enough for it to be so, but for those of us who dealt with him daily, we knew him as a lovable combination of Dwight Schrute from The Office infused with the wiles of Dan Egan from Veep. In fact, the folks who worked at Veep met with Schultz before their show aired to nail the eccentricities of Washington’s elite. Schultz rushed through personal pleasantries so perfunctorily that they weren’t pleasant at all. He loved perks and was uncomfortable around babies. Like many Washingtonians, he could be transactional by nature, but he had a good heart, and he was as gifted and sophisticated a press person as you could find anywhere. When things went haywire, the White House often turned to Schultz. He would know what to do, which is why he was a regular member of the “red teams” that popped up in preparation for complicated rollouts or in the wake of pseudoscandals. He had the right combination of drive, discretion, and decency—mixed with an entertaining flair for the dramatic.

  Noticing the open box of candy, Schultz continued, calling out, “Did I get screwed out of snacks again?” Throughout his tenure, Eric was known for simultaneously trolling for treats around the West Wing and for his fruitless pursuit of a personal trainer across DC who would be willing to put up with his hectic schedule.

  Velz, a persnickety press assistant famous for his eye rolls reflecting a thinly veiled sense of superiority, and for overseeing the communications interns, sighed. “They’re from the interns.”

  “And what am I, chopped liver?” Schultz demanded.

  “Can you even name an intern, Schultz?” Howli asked.

  “No, but that’s because none has ever made an impression on me,” he replied with his signature head swivel and a quick check of his watch. A nervous tic.

  “Schultzy, I was one of your interns,” Velz reminded him. This warranted a major eye roll.

  Without missing a beat, and with the knack for spin that made him so valuable, Schultz retorted: “And I don’t want to take all of the credit, but look how well you turned out!”

  “There it is!” Desiree interjected. “A white man trying to claim credit for a minority’s success.” (Velz’s mother is from Thailand.) Desiree was my desk mate and good friend—though neither of us would admit it. She started with the Obamas as an intern very early on and was a standout member of the advance team before moving into her role as a wrangler and, later, as a special assistant in the West Wing. An African American woman my age, Desiree had a habit of turning her quick wit on me.

  Upper Press was a diverse work environment, though no thanks to me. For a few years, aside from the press secretary, I was the only white guy working there. And for the duration of my time, women outnumbered men. Diversity in our workplace never seemed forced. It felt organic, like the pool of talent drawn to President Obama came from every background imaginable. Our differences were our strength, but they also provided plenty of opportunities to call out one another, to erupt in mock indignation, or to have a little fun at one another’s—or our own—expense.

  There was an openness to talking about race in the office, and there were many jokes we could all get into comfortably. But there were some we couldn’t, and Desiree was particularly skilled at screeching the conversation to a halt when I overstepped, or, more frequently, when she could pretend I did for the good of the room. I was the foil, after all.

  “Yeah, Schultz, do you really feel comfortable taking any of the credit?” I asked. “I’d say that’s red-zone material, right, Desiree?”

  Red zone is what somebody would inevitably announce when things were going south in Upper Press; when we were veering into awkward or potentially offensive territory. Now, given that I was considered a repeat offender, Desiree kept a Post-it note between us titled “Red Zone.” She tallied—often unfairly, to my mind—each time I crossed the verbal line. I was desperate to get somebody other than myself a tally.

  “No, Pat. This is one thing that you—as a straight, white, privileged man—do not get to be in charge of. You don’t dictate tallies to me. In fact, that in and of itself is red zone!”

  Schultz, foraging through the food, ignored us both and turned to Howli. “I have something for your boss. It’s timely, so if you could get me a few minutes, that’d be great. ’Kay, thanks.”

  “He’s in the Situation Room. And this better not be about Louie.”

  “Totes! T-Y,
T-Y!” Schultz shouted to Howli as he dashed down to his small office in Lower Press, donut hole in hand.

  Louie is Schultz’s dog.

  • • •

  Bo and Sunny, the First Dogs, liked to rustle around what we called the “burn bags”: they looked like trash bags, after all, and we threw a lot of uneaten food from the press into our regular trash cans. These free-standing brown paper bags with burnt orange lines zigging and zagging around them were strewn throughout all of our offices. They were meant to collect our work-relevant papers, especially anything that was sensitive or classified. When we ran out of use for a particular document, record, or page of notes, we’d “burn-bag it.” That was a misnomer, however, as the glorified trash bags weren’t all sent off to be scorched into oblivion. Some turned into a catch-all for relevant and semirelevant documents that we didn’t know how to discard.

  The two Portuguese water dogs had free rein of the place, bounding up and down the stairs, barking their way through the Outer Oval Office and into Upper Press. During the day, when the First Family wasn’t in the residence, Dale, a longtime, trusted employee of the White House grounds, helped to mind them. As head groundskeeper, he was always on the move, which made him a perfect fit for helping to tire out the dogs. Sometimes they got loose, though, without Dale close behind, and went foraging for food.

  Bo had done just that, inspecting the trash can by my desk, sniffing the remnants of a “Chocolate Freedom”: an extravagant chocolate lava cake with soft-serve vanilla ice cream in a cup on the side, prepared by the White House Navy Mess. (Upon ordering one for himself after his famous interview with President Obama on the internet talk show Between Two Ferns, comedian Zach Galifianakis asked if the Chocolate Freedom was named after Obama himself. It wasn’t. Rumor had it that it was made of French chocolate, and in the madness surrounding “freedom fries” and France’s opposition to the invasion of Iraq, the George W. Bush White House deemed it the Chocolate Freedom.) We looked for any excuse to order them: somebody’s last day, a birthday, whatever.