West Winging It

by Pat Cunnane

  In short, story mattered.

  “So whether that’s Alex, the 6-year-old kid talking about refugees, or Brent, the GOP Wisconsin letter-writer talking about ACA, or Virginia McLaurin, the 106-year-old woman who danced with POTUS and FLOTUS at the Black History Month reception, they are all personal, emotional stories that convey American themes and values (and values represented by Obama) in powerful ways,” Jason explained. His findings on what broke through validated what we had been trying to do for years with RPs and tracked with Americans’ ability to see themselves in President Obama; to see their family in the First Family.

  So I was optimistic when Brent stepped to the podium. My worries were misplaced. Brent’s correspondence with the president and then with me wasn’t rambling or illogical, as I had feared, it was of a piece, sincere—and deeply moving. His words, passionately placed one after the other, email after email, were in communion with his experience.

  We’ve stayed in touch, become something of pen pals, and every time I finish reading one of his long and winding notes, I am rejuvenated, invigorated by his story and therefore by the president’s story. Brent always states explicitly what he told the world when he stepped behind the presidential podium:

  The president saved his life.

  After recounting that he had never voted for Obama and the ways he had cursed the president’s name, Brent humbled himself before the crowd and the cameras, relaying that due to a serious disease, he was driven to bankruptcy, unable to receive care. “I was literally a dead man walking,” he told me. His hope was gone. But then, in front of the world, he said something changed. “But then this guy signs this bill . . . thanks to his fortitude, thanks to his unwavering visions of mercy even toward me, this chump gets a second shot at life . . . I was worth saving. We are worth saving.”

  Brent’s introduction was viewed something like fifty million times. He lost many of his conservative family and friends as a result. But, as he’s told me, he gained some new ones, too—including a former president named Barack.

  • • •

  Obama rightly considers himself a writer. It sometimes seemed like that’s what he knew, at a base level, was his thing, his primary talent. Before professor, before politician, before president. Writer. Author. Speechwriter.

  He is also an insatiable reader. Beyond his onerous nightly briefing book, which I was partially responsible for helping to fill to bulging proportions with event memos, draft statements, and op-eds, as well as decision memos and—most time-consuming of all—interview prep materials. To say nothing of the far more important sensitive or classified documents in his massive binder—more than enough reading for a week, let alone a night.

  Still, he found time to read widely. From Marilynne Robinson, to Maurice Sendak, to Abraham Lincoln, to Gillian Flynn, the president became a sort of reader in chief. We even took to releasing his vacation reading lists and set up a number of conversations with authors and interviews specifically about his reading habits.

  The press seemed to sometimes perceive an aloofness to the president, but I think that was born of his unique take on his job. Beyond political machinations, he seemed more interested in what motivated human behavior. Standing in countless Oval Office pool sprays, minding the press, I could almost see him studying the moment even as he was the center of it.

  His reading fed into that. He used books the same way most of us do: to learn, to get out of our own bubble. Like hearing from letter writers, escaping into a book helped to put him in the place of others. To empathize. Earlier in his life, they provided a foundation of knowledge, an undercurrent of information that he would draw on as senator, president, and parent. As he has said, during his final two years of college, Obama sequestered himself, studying the texts of the world’s great philosophers. He has admitted that he may have gone overboard in those years and taken himself too seriously. But those readings no doubt contributed to his vast perspective, helping to contextualize his time in the Oval Office.

  My favorite book, as I might have mentioned, was Sinbad’s Guide to Life, so safe to say I was out of my league. But the president did like to write first drafts of speeches on yellow legal pads, so we had that in common. I looked up to his prose, was awed by his rhetoric, and shared his love for writing.

  My mom, a professor of writing and rhetoric before she entered politics, ensured that my brothers and I could write, and write well. She mentioned Strunk and White (William Strunk Jr. and E. B. White, authors of the writers’ bible The Elements of Style) so often around our house that you could be forgiven for thinking they were relatives.

  The first piece of writing I did that garnered a bit of attention was in fourth grade. We had been asked to write about our hero, an assignment my teacher, Mrs. Montgomery, was eager to review during parent-teacher conferences.

  I began the essay by lauding my dad. He rode his bike across the country, I noted, adding that now he had his own bicycle company. And did you know he saved my uncle’s life, leaping in front of a falling wall?! It was a one-page paper; I spent the first four-fifths on my dad’s heroics and business acumen before turning to my mom, a remarkably impressive person in her own right, for one sentence: “My mom likes fine hotels and happy hour.”

  “Just coming from happy hour?” my dad cracked as my mom entered the classroom a few minutes late. Mrs. Montgomery nearly fell out of her seat.

  It’s the same reaction Desiree gave me when I showed her something I was proud of: my first peer-reviewed and accepted piece of writing. For the online Urban Dictionary.

  You see, for much of President Obama’s second term, I had been trying to make a saying that I came up with—“Got that sun in your eyes”—catch on around the West Wing. I define “Got that sun in your eyes” as “behaving differently due to proximity to someone or something deemed cool,” something that tended to occur when celebrities stopped by, which happened more than I could have ever imagined.

  Truth is, the White House is practically Hollywood East. Major stars came through constantly. Sometimes to be honored. Other times to meet with the president. And frequently just to check things out and get a tour from a staffer.

  I remember one Sunday morning when I entered the White House and regretted momentarily that I hadn’t showered. Oh well, it’s Sunday, I thought. Who cares if I look god-awful? No one will see me. No sooner did I take my seat than the door creaked open, and in walked a bevy of beauties. Only these weren’t just any beautiful people. These were three Hollywood A-listers: Kate Hudson, Reese Witherspoon, and Kate Upton, just checking things out. I really regretted not showering.

  Speaking of showers, another particularly memorable drop-by was Bill Murray, who hung around the West Wing for the better part of an afternoon when his beloved Chicago Cubs were playing the Washington Nationals in the 2016 National League baseball playoffs. He came into Upper Press to our shock, just sort of ready to hang. Desiree, who was not shy and rarely had the sun in her eyes, prompted a discussion of golf—a mutual passion between Bill and me—which led to an uncomfortable conversation about the showers at a course we had both played recently. We chatted about water pressure, heat, and the awkward fact that there were no doors to the showers.

  Eventually Desiree grabbed my phone and showed Bill videos of my golf swing. As he began to critique my form, I snapped out of the moment and thought about the insanity of the White House, this place where anybody in the world was just a call away. A surreal beehive of bizarre activity. Visits from folks like Bill Murray and Bruce Springsteen, George Clooney and Leonardo DiCaprio, added to the lore of the place and the sense that I’d had from my earliest days across the street: that the West Wing was some Hollywood set. But this was real, and as Bill Murray exited our office, he turned back to me with a piece of advice: “You should thrust your hips more. You’d hit it farther.”

  “Thanks.”

  “Plus, you’d be a hit on the dating scene.”

  • • •

  Gradually, I imp
roved my own writing, mechanically and substantively. My mom would teach her students that the best of writing is the intersection of strong writing skills, experience, expertise, and humanity. The first three I got: mechanics matter; life experience matters; and knowledge matters.

  It was the last element that mystified me. What’s the humanity notion? How does that fit? My mom would tell me and her students that good writing leaves an impression most when we feel the warmth of the writer behind the words, when we sense her uniqueness—his humanity. That’s when words “sing,” she would say.

  You knew it when you heard it. And I heard it in 2004 when I was just sixteen, and a little-known senator with a name I couldn’t at first pronounce burst onto the scene, reading the words he wrote about the country he believed in. Even twelve years later, it remained true. The greatest story Obama told was America’s. In place after place, in small towns and on the biggest of stages, he was an advocate for America with a writer’s touch and a storyteller’s grace.

  I wanted to be a part of it. After I’d had “writer” tacked onto my title in 2013 by Katie Beirne Fallon, I tried to play it like a benign bump in position, no big deal—an excuse to pay me slightly more than the White House minimum. Truth is, on the inside, I was beaming. Writer. At the White House. I couldn’t believe the way things were falling into place. Maybe I’d get to write something that mattered.

  Of course, most of what I began with was bottom-of-the-barrel writing. I started with dry memos to the president, glorified logistical documents, before adding guidance memos, in which I helped guess what questions the president would be asked and suggested what he should say in interviews or press conferences. I became a choke point between staff sec and the communications department, which prompted countless calls from Ted.

  Upper Press proved a challenging place to concentrate on writing. The area was chaotic, frenzied; to help me concentrate, I’d blast music into my headphones—usually 1990s pop music; sometimes the Canadian band Soul Decision—to cover up the conversations around me.

  The president once popped into Upper Press unannounced while my headphones were in. I half stood and anticipated his “How ya doing?” answering with a fervent “Excellent!” Only, that’s not what he asked. As he turned away from me, a little faster than usual, I realized he had actually inquired how my golf swing was. Mine was the antithesis of the right answer to the question. Golfers are perennially in the process of tweaking this or tuning that; only goons think their golf swings are “excellent.” Golfing is a language, and I had duffed my answer. The president left without a word, and I was confident that I wouldn’t be invited into his foursome anytime soon—and also that I wasn’t always so good at predicting what he planned to say.

  I certainly couldn’t have predicted that I would indeed get one more invite to the golf course. Previously, I had played in the group behind him a number of times on his annual vacations to Martha’s Vineyard and Hawaii. But this time, I was asked to play in his group. It was late fall, the day after Thanksgiving, and it was cold; I hadn’t swung a club in months. But I jumped at the chance—I’m going to play golf with the president of the United States!—departing before dawn from Cape May, New Jersey, where I was celebrating Thanksgiving. I drove to JBA in Prince George’s County, Maryland. I was so eager that I arrived hours early and posted up at a McDonald’s just off the base, taking a few practice swings in the parking lot.

  Joint Base Andrews didn’t have the best courses in the world, but it was convenient for the Secret Service, so the president played there often. As I approached the first tee, I was met by a former staffer a couple years older than me, who was a frequent presidential golf partner, and a man in his fifties who worked at JBA and would be joining our group. We heard the roar of the motorcade and then the softer growl of dozens of golf carts—including one that was armored—parading down to us. “Let’s do old guys versus young guys,” the president announced as he arrived on the tee box.

  Most of the round went off without a hitch. I played better than expected—even got a lucky bounce off a Secret Service golf cart flanking the fairway and back into play. After about the fourth hole, you begin to forget you’re playing with the president. You loosen up and ignore the scores of armed men and women watching your every putt. That’s because there’s a ritual to golf; an honor system and an unspoken tradition. The president doesn’t putt first just because he’s the president. Whoever is “away” (farthest from the hole) putts first. The president’s no less immune from shanked shots than the rest of us. So we joked and talked about sports. The game seemed in some ways to serve as an equalizer—that is, until the match got tight.

  By the seventeenth hole, the president’s team had the chance to put us away and win our friendly wager. To my shock, I sank a twenty-foot putt and kept our team alive. I was feeling pretty good, basically strutting my way to the eighteenth tee, where the match would be decided. As I stood over the ball, the president said:

  “Fairway’s pretty narrow out there, isn’t it?”

  Oh my God. The president’s trash-talking me.

  But I felt emboldened by his taunt, telling myself I was going to stripe it down the middle as I took the club back like I’d done so many times before. I felt good at the top of the swing before snapping my hips forward, like Bill Murray suggested, whipping the club through the ball and right down the midd—Nah, I hooked it into the woods.

  I navigated my way through bushes and beneath massive trees to find my ball, perched hopelessly under a thorny bush. I was surprised to find the president right behind me. “Make sure you play it as it lies,” he said good-naturedly before heading back to the fairway, where he was in the line of my next shot.

  I debated hitting it backward to avoid asking the president to move, but the match was on the line, so I yelled from the bushes. “I’m coming right toward ya, sir!” And he hopped in his cart and moved out of the way. I dribbled the ball out toward him and had an approach shot that needed to be on point to have any chance at squaring the match. Instead, I launched the ball well over the green.

  As we approached the eighteenth green, the president continued over to where my ball sat. A Secret Service agent chimed in, “Sir, your ball is on the green.”

  “I know,” the president responded. “Just wanted to see how rough of shape Pat is in.”

  I ended up triple-bogeying the last hole.

  We lost.

  But at least I made an impression.

  I remember at the very end of President Obama’s second term, he graciously took photos with staffers and their families in the Oval Office; each night, he would sign a bunch of the photos upstairs after work with a one-line message, usually thanking the staffer for his or her great work and service. I was looking forward to mine. A piece for the mantel. I’d pass it down to my grandchildren one day. Then I heard the laughter.

  Velz got word from the Outer Oval that something was up with my photo. I thought maybe they’d pranked me and had the president sign the horse photo or something. Velz delivered the photo to my desk with a smirk. Apparently, a bunch of people had seen it already. I opened to find the photo of me and my family—so far, so good—and the note below in Sharpie: “Pat—Thanks for the great work . . . and the foursome!”

  “. . . and the foursome!”

  That was not the language of golf. Just like you never say your swing is “excellent,” you don’t say “thanks for the foursome.” “Thanks for the round” would have been the more likely wording. But the president’s awkward phraseology was a fitting way to end my time in the West Wing, given how it began with Sean and the taxicab. Most of all, it was another reminder that I couldn’t predict what the president was going to write.

  Still, like I was saying, in the second term, I tried. I started with presidential quotes. Somebody just got nominated as the railroad administrator? Somebody needed to compose the generic sentence of support from the president. With Strunk and White dancing in my head, I set out to mak
e every bland statement purr. Before I knew it, I was writing a few statements each week, usually with little notice and even less time to pull something together. The topics ranged widely, from members of Congress retiring, to one of my specialties: death statements.

  When celebrities, politicians, or other notable people passed away, the president often wanted to pay his respects in writing, and I was always happy to jump in.

  The process, though quick and frenzied, usually took shape the same way: swift information gathering on my end: What’s the president already said on the topic? Do we have a policy paper on the issue? Sometimes I needed to hop over to Wikipedia for a quick lesson in whomever or whatever I was just tasked to write about. Then I’d whip something up as rapidly as possible—sometimes I had a day; other times, an hour—and I’d get it around for review from the appropriate policy council, the lawyers, the chief speechwriter, and, most importantly, our much-admired research department. Ask anybody from the Obama White House, and they’ll tell you that the research department was the hardest working. The staffers there logged longer hours than anybody and rarely enjoyed a free weekend. They were on call in times of crisis, but they were also tasked 24/7 with helping us to avoid the crises in the first place—an almost unbearable pressure that they bore with good humor. They checked facts and kept us honest, and no statement was ready to go until they signed off.

  Sometimes my statements and jokes, op-eds and quotes, didn’t need clearance from the Oval Office. It wasn’t exactly the State of the Union, after all. But, to me—the memory of my mom’s yellow legal pad and my first glimpse of Obama at the 2004 convention on my mind—it might as well have been.

  For the more important statements, there was one last person outside of the research department who needed to lay eyes on the thing—and he was the best writer in the building. I remember in early 2016, I was asked to craft a statement from the president about Aretha Franklin for the New Yorker.