West Winging It

by Pat Cunnane

  The stakes were higher for this sham. As Friday neared, my nerves increased, and by the morning of the proposal, jitters were jumping through me so much so that I couldn’t sleep. I arrived at work earlier than normal.

  By early afternoon, Jay couldn’t help himself. He approached my desk, and I knew what was coming.

  “I know, I know,” I said, preempting him. “Bashar al-Assad, yada yada yada.”

  “No,” Jay said. “I just heard today’s the big day, and I wanted to say—”

  “Oh, thank you,” I said, feeling like an idiot.

  “No, I gotta say, you don’t look great.”

  “Huh? I didn’t get much sleep,” I protested.

  “You should really go home and shave.”

  And so I did. I walked briskly up Sixteenth Street to the filthy studio apartment I was renting. Stephanie arrived early from Philadelphia as I was getting out of the shower, so I hid the ring box in my hanging sock cubby just before she walked in. My plan was to stay with Stephanie and walk back to the White House together. Then I received an email from Marie. The subject line began: “Don’t freak out, but . . .”

  I was absolutely freaking out. Marie explained that the president’s schedule was shifting. We might miss our window and lose the light. I didn’t have a backup plan, hadn’t considered that something might not work out. I had gotten a bit too comfortable in the environment. A slow Friday could feel like a bit of a flophouse—like any office counting the minutes until happy hour. I neglected to consider, as I had learned time and again, that the tenor of the place can change in an instant, with fun plans scuttled just as quickly. To compound things, both my family and Stephanie’s family were waiting at a nearby hotel to celebrate our Rose Garden engagement. They had come from across the country to be there. I shaved quickly, rustled through my socks and grabbed the ring, told Stephanie the party was delayed slightly due to a minor work emergency, and rushed back into the office.

  The Oval Office looks squarely into the Rose Garden. Often, when the sun has only recently disappeared beyond the monuments and the Mall, the Oval remains alight, and the room’s glow seeps through its sizable windows, partly illuminating the Colonnade and the Rose Garden, but not enough for my plan to work. I couldn’t let it get to that point. The pictures wouldn’t turn out well.

  A Secret Service agent stands guard along the Colonnade whenever the president is in the Oval. I checked as soon as I arrived. The agent was there. But the Rose Garden was still bright. I consulted the president’s private schedule again. He was supposed to be finished for the day. What could possibly be keeping the leader of the free world at work late on a Friday night, I asked Marie and Antoinette, irrationally frustrated.

  “Calm down, Pattycakes,” they told me. “It’s going to work out.”

  I took a seat at my desk in Upper Press to try to do just that, but then coworkers who had heard the news started coming out of the woodwork, popping in from all corners of the West Wing. Jay walked in with Gene Sperling, one of the president’s top economic advisors, and explained what I was about to do. Now, I hadn’t previously worked at all with Gene—known around the West Wing as the Gene-Machine—but he piped right up.

  “Can I offer you some advice?” he asked.

  “Please.”

  “She might say no.”

  “That’s advice?”

  “Hey, I’m in politics,” the Gene-Machine reasoned. “It’s all about expectation setting.”

  I couldn’t sit around any longer; time to get things in motion. I took a flier and, with time winding down, sent Stephanie a note to head toward the White House. I promised I would meet her at the northwest gate in front of Lafayette Park. As she made her way down Sixteenth Street, the president—mercifully—crossed from the Oval, down the Colonnade, through the Palm Room, and up to the residence.

  Relieved, we took our positions. Marie dashed through the Briefing Room to grab Evan, a photographer from the Associated Press who’d agreed to surreptitiously photograph our engagement. Antoinette jogged out to the gate to meet Stephanie, and I took up a spot on the Colonnade. It was then that I realized, for all the crap they were giving me, much of the West Wing had stayed late on an otherwise slow Friday to help out. Ben Rhodes, a deputy national security advisor with many more important things on his mind, volunteered to block the double doors to the Colonnade, so that no one would interrupt our moment.

  Stephanie told me later that she was annoyed with me for abandoning her at the apartment and doubly perturbed when I was nowhere to be found at the White House. She was mystified when Antoinette grabbed her from the gate, insisting on removing her security badge and taking her purse. But then Antoinette pushed her out to the Rose Garden.

  I was waiting on the Colonnade. Truth is, I don’t remember much more after this. I took her hand and walked her through a small clearing in the bushes toward the center of the Rose Garden. I spoke for what seemed like an eternity—in varying degrees of coherence—and then took a knee. I remember hearing the familiar click of a camera but didn’t know where it was coming from. Stephanie doesn’t remember what she said either, but she was nodding her head over and over, which had to mean something good. She said yes!

  We walked back to the Colonnade and down to the Palm Room. I saw Marie and Evan the photographer jump from the bushes to the Palm Room to capture more moments. When we got to the Palm Room, we celebrated.

  “This was my favorite wrangling job yet!” Marie exclaimed.

  My family was waiting for us at the hotel, but as Stephanie and I stepped down into Lower Press, where everybody was waiting—Matt, Bobby, Howli, and others—I realized that I was developing another family. An Obama family. And I didn’t want any of this to end.

  • • •

  Even in the afterglow of our engagement, as the White House felt more like a second home than an office, and just when I was finally getting the hang of things, polls and bumper stickers, attack ads and obnoxious buttons, were constant reminders that it could all come crumbling down on Tuesday, November 6, 2012. Even while Obama seemed to command a comfortable lead, Dan, Jay, Howli, and others—all more experienced political hands than I was—warned me not to worry too much when things tightened.

  The gap between the two candidates would inevitably, and naturally, begin to close. After all, gaffes would be made. Many of the all-important undecideds would soon decide to “come home” and vote the way they usually did. Most of all, a close race—or the perception of a close race—benefits the media. So it would have to be. For months, the Obama campaign had capitalized on Romney’s proclivity for goofy gaffes, foremost among them his attempts at appealing to Middle America by talking about how some of his friends own NASCAR teams, as well as his caught-on-audio comments about nearly half the country:

  “All right, there are forty-seven percent who are with him [Obama], who are dependent upon government, who believe that they are victims, who believe the government has a responsibility to care for them, who believe that they are entitled to health care, to food, to housing, to you name it. My job is not to worry about those people. I’ll never convince them they should take personal responsibility and care for their lives.”

  Now, that was a doozy, damaging in the way that the worst gaffes so often are: they provide seeming proof of a notion that many voters already have about a candidate. In this case, that Mitt Romney is rich and out of touch. And they can be boiled down into a quick turn of phrase rebutting the candidate: “I am the 47 percent.”

  Obama slipped up and flubbed a line that fit all of the same criteria. Campaigning in Roanoke, Virginia, as he was speaking about the unique opportunities our country and way of government has provided for its citizens, Obama told a hypothetical entrepreneur in reference to his hypothetical business, “You didn’t build that.” You didn’t build that. I knew the second he said it, it didn’t sit well. Sure, I understood what he was going for—that the hypothetical entrepreneur no doubt benefitted from America’s infr
astructure or technological advances from the military or any number of other benefits of living in the Land of the Free—but it didn’t ring right rhetorically. And the Republicans seized the opportunity. I did build that.

  The gaffes both candidates made during the summer of 2012 seem quaint when considered through the looking glass of the election that would follow, but on the trail, they haunted us into the fall.

  Tension ratcheted up as the first presidential debate loomed in early October. Still, as I pulled into debate prep in Henderson, Nevada, I felt fine, buoyed by a seven-point lead in the polls and ready to spend some time at the pool—rather than with the pool. Meanwhile, the president and his team, with Senator John Kerry of Massachusetts playing Mitt Romney, ran through mock debates on a stage nearly identical to the one that waited in Denver. It’s common practice to prepare for presidential debates secluded from the distractions of DC in a retreat-like setting. So our motorcade snaked along the highways of Henderson as always, but things took a turn—literally and figuratively—as we approached our hotel, with nearly five hundred rooms, about twenty miles outside of Las Vegas.

  As we advanced, something was becoming abundantly clear: we were entering the hotel equivalent of a ghost town; a onetime luxury resort with no guests. No hubbub. Nobody lining the streets looking at us, zero signs waving, no clapping from supporters and no middle fingers raised by detractors. There was another way folks along the motorcade route expressed their displeasure with the president that was actually more offensive than the middle fingers: they would dramatically turn their backs to the motorcade as it passed. It was a particularly effective form of silent protest, in that it really caught our attention. It irritated me every time. And yet it was also wonderfully American. To openly gripe about your leader, even in his presence, the kind of action that helped make America great in the first place. I got the sense that those middle fingers and turned backs didn’t bother President Obama quite so much as they did me.

  But there was no one to turn their backs on us as we continued along the vacant hotel grounds—driving through an overgrown, grotesquely unused golf course, and passing a vacant high-end shopping center constructed with man-made water features to look like it sat on a quaint river bluff in Europe. The ride was eerie. Like Disney World the day after the apocalypse.

  I sent Marie a text: “This place is odd, right?”

  She filled me in on some of the details. Turns out the resort defaulted on its mortgage during the economic crisis of 2008–09, which hit Las Vegas and its surrounding cities particularly hard. The city was coming back, but not as quickly as most would like. Insofar as the 2012 election—like all elections—was about the economy (stupid), and a referendum on whether the president had done enough to jump-start our economy, Henderson was a troubling spot to choose for the president to hone his argument for the American people about why his vision for economic growth continued to be the best one. It was the ideal dateline for a snarky think piece waiting to be written by one of the slightly bored journalists hanging around the hotel pool with me as the president worked diligently behind closed doors on his economic talking points.

  We would have three days here. Three days for Obama to refine the rhetoric, adjust the arguments, memorize the statistics, and practice a punchy line or two—before stepping in front of seventy million Americans (plus the dulcet-toned Jim Lehrer, the recently retired PBS NewsHour anchorman) and the man who had been campaigning for months to put the president (and all of us) out of work. Three days before America really started to pay attention: Do we want to keep this guy or try something new?

  It’s a truism that most incumbents lose the first debate. Thing is, nobody told me that. So by the time our three days in Henderson were up, I was optimistic, confident as we landed in Denver, excited as we rolled down the cleared-out highway, that my boss would wipe the floor with Romney.

  There were omens, though, that suggested we might be in for a surprise. First, our motorcade driver was nuts. The motorcade becomes so unwieldy in its length when traveling outside of DC with the president that we often rely on volunteers to drive many of the vans toward the back of the convoy. The driver assigned to the press van I was fortunate enough to ride shotgun in, bless her, did not understand the basic concept of the motorcade: the idea that, above all, we must stay together.

  Now, these drivers are not pulled off the street and thrown keys; they are instructed exactly how to drive. We have an advance staffer fully dedicated to the motorcade. And I do mean dedicated. One of my favorite advance staffers, Tim Sneed, had developed a bit of road-show glory, known for his cowboy hat and the moniker Tim-Sneed-Motorcade, which was how most people referred to him. He packed dozens of Matchbox cars for every trip to simulate a miniature motorcade. There’s a very distinct order into which the motorcade’s vehicles are arranged. Absent a breakdown, there’s no passing in motorcades—so the convoy is only as strong as its weakest rental van. In Denver, mine was the weakest link. We were delaying the cars behind us. I didn’t want to be a back-seat driver, but we were threatening to chop the motorcade in two.

  “You should really keep a little closer to the car in front.”

  From that moment on, she overcorrected, and every time the string of vehicles tautened, we’d nearly slam into the van ahead.

  “Brake!” I’d yell. The reporters’ cameras and laptops would go flying forward.

  Eventually I had to stop looking at the cars ahead; it was too nerve wracking. So I focused on the billboards that went whizzing by until a striking advertisement loomed in the distance and grew larger as our driver lurched us forward. A darkened photo of a dour-looking Obama came into focus, shouting down at all of these swing-state passersby trying to get to work: “You didn’t build that!”

  I nearly refound religion on that ride. A photographer or two kissed the pavement when we pulled up to our destination. But we’d need more than faith for what would come next.

  We knew we had lost the debate within the first ten minutes. Twitter said so, but I didn’t need them to tell us. Truth is, my gut had dropped by the end of the two-minute opening statements. Each candidate had made a joke about it being President and Mrs. Obama’s anniversary, but Romney’s landed better; he actually got the bigger laugh. It was a precursor: his lines would resonate with the room all night. Obama seemed listless, whereas Romney came to play, finally on equal footing with the president. He “looked” the part. I had never been to a debate before and didn’t really know how to watch one. So I took it in like a Philly sports fan. We’ll come back, I kept telling myself. This is our year. He’s got to win.

  He didn’t win.

  “Let’s get the hell out of here.” Like two grousing Phillies fans trying to beat traffic, my coworker Nick and I darted out of the “spin room” (there was no spinning this in my mind) and dashed into a waiting car, where a Democratic volunteer would take us back to the hotel.

  “What happened in there?” the driver asked.

  “Nothing good.”

  Marie, on the other hand, was with the pool, rushing from the arena back to the vans. They all piled into the motorcade, where their volunteer driver had a different take. “Wow, he was great tonight!” It’s easy to be blinded by partisanship, but this was such a decisive loss that even my nana was momentarily disappointed in her Barack. Still, Marie ran with it, nodding along in disbelief until the driver piled on, mentioning how proud he was of . . . Mitt.

  Marie turned around to the reporters filling the three rows behind her and shared a moment of panic.

  “Run!” Marie shouted.

  They were unwittingly behind enemy lines. “Wrong motorcade!” They swung open the doors, sprinted down the road and barely caught up to the correct motorcade, where their driver, an Obama volunteer, was waiting nervously. She had been worried that the president’s debate performance was so bad that everybody had jumped ship and literally climbed aboard the Romney bandwagon, leaving her van empty.

  • • •r />
  On Election Day 2012, our motorcade was a bit different. Rather than the bland vans to which we had become accustomed, our advance staffer Jeff hooked us up with a party bus that was more suitable for a bachelor party than a presidential motorcade. There was booze, swanky leather chairs lining the walls, and decorative lighting, as well as an impressive sound system and a mirrored ceiling. Marie, the pool, and I were grateful for Jeff’s creativity. We would be in the van for many hours on November 6, 2012. Election Days are about active waiting—the party bus was a nice place to do it.

  Obama had bounced back after the first debate knockout, and our side had finally begun to rationalize the subpar performance. Much of Democratic Twitter had melted down at first. In fact, Andrew Sullivan’s take was so bleak that Dan put a moratorium on our media monitor (Velz at the time) sending around the Newsweek/Daily Beast writer’s increasingly terrible analyses. Obama’s predebate polling edge had been chopped in half, but we were still up, and our path to 270 electoral votes was much more clear than Romney’s. The polls would need to be overwhelmingly wrong for things to go against us, and we had no reason not to trust the polls. So things looked good as we boarded the party bus, escaping the early-morning Chicago chill outside of President Obama’s family home.

  We’d been up since before dawn and didn’t expect to sleep again until the next day. The long nights, ten-day travel stretches, the debates and commercials, the OTRs, bus tours, and slogans had all led to this day: America was voting! While we waited, we popped into a local campaign office for some phone banking. The president, in shirtsleeves and black-and-gray striped tie, took to the phones, greeting breathless volunteers and chatting on the phone (when they didn’t ignore the call) with Chicago-area voters. Beyond that, we mainly waited. We asked: “What have you heard?” Nobody had heard anything. We wondered: “How are you feeling?” Everyone felt the same: nervous.