by Pat Cunnane
I thought back to my own wedding on a balmy July evening in downtown Philadelphia. Like most surreal events, I now see my wedding through a series of flashes—what I saw, stories I heard—that congeal to form a sense of the night: Stephanie turning the corner of the aisle with her dad. My inability to get through the ceremony—crying from the moment I saw her until we both said, “I do.” My brother Alex, in his tux with the bridesmaids, leaping into the fountain at Logan Circle—and then demanding, dripping wet, that the receptionist call Taylor Swift, who was apparently staying on our floor. Marie and Antoinette presenting me with a framed photo of my engagement in the Rose Garden, with a note from the president.III My dad’s moving speech, told in bicycle terms, and my pop-pop dancing in his seersucker suit.
I thought about the faces of the people, my family and lifelong friends, dancing alongside so many guests—my White House family—who were unknown to me just a few years before. Young people I didn’t grow up with from across the country who came together around an idea embodied in a skinny guy with a funny name from the South Side of Chicago. They weren’t friends I had my whole life, but that didn’t matter, because you get to know people quickly in the White House, where stress is high, days are long, and everything’s accelerated in the foxhole.
Seeing the different people from disparate parts of our lives come together to party was one of the most rewarding facets of our wedding. We didn’t look alike. Hadn’t grow up in the same way. But my White House family and I had something important in common, highlighted by Dan, the second thing he did before he left the White House.
I read hundreds of obligatory “goodbye” emails from departing staff during my years at the White House, but something Dan wrote stood out. He said that no matter where we went or how many years passed, we would forever be known as “Obama people.” I took comfort in that as I walked out of the gates for the last time.
I thought about a million little moments. Asking Matt, “What’s a POTUS?” Getting red-zoned. That absurd photo of me on a horse in the ocean regularly circulated by Velz and others. Swing states and debates. I thought about Susan Rice opening that horse email and Josh replying to the whole White House, “Giddy-up!” The thrill of 2012. Proposing to Stephanie in the Rose Garden. Lester Holt at Nelson Mandela’s funeral. The despair of 2016. Bringing my mom and dad, Stephanie, Harry, and Alex into the Oval Office to meet the president. The Pope sneeze and Seinfeld’s squeaking sneaks. Shaq. I thought about walking my nana and my pop-pop through the West Wing, before they could no longer travel. The Door of No Return. Watching an inauguration from the Atlantic Ocean. Then, the Blue Room. These were the moments that marked my time winging it. West winging it.
After all, a presidency is defined by a series of moments, for better or worse. Some of those moments flashed through my mind: Signing the Affordable Care Act into law. SEAL Team Six and a red line in Syria. Reaching over the sneeze guard at Chipotle. A baseball game in Cuba. A beer summit and Trayvon Martin. Announcing that America would wind down two wars. Wearing a tan suit. An attack in Paris. “Amazing Grace” in Charleston, and Aurora, and Newtown, and Orlando. Hope and hard-won change.
• • •
But I was drawn to the quieter moments as I drew closer to the gates one last time. I thought back to five years earlier, when I had wrangled my first late-night Marine One arrival. In the middle of the night, the White House takes on a haunting, midnight melancholy. Stillness replaces frenzy. Suddenly from above, three points of light—Marine One and its two decoy helicopters—become visible from the South Lawn. Watching the chopper carrying our forty-fourth president throttle past the glowing monument to our first president, I was struck by the thought: one day Obama will be a monument.
That same idea would occasionally pop into my mind in the Oval Office: I’m talking to a battleship, likely a bridge, too—an international airport, as well as countless future high schools. But for now, he was the person landing before me on his backyard.
The strong winds of Marine One leave an impression. At once, everything is tossed about, but at once, you’re confident everything will be all right.
Obama bounds up the South Lawn, across the drive, and into the Dip Room. The doors close behind him, and the helicopter, no longer Marine One, lifts away into the night. The stillness returns. And the anxieties of the world seem to hold in abeyance until the sun peeks over the tidal basin by Jefferson when the White House comes back to life. By the time the sun reaches the top of Washington, the day is in full swing. And as the sun sinks beyond Lincoln, calm sets back in.
• • •
I think about Obama people, about granite and grace and generations to come—their kids, my kids—as today’s Obama people become tomorrow’s Obama family, and we expand beyond the gates of the White House. I think about monuments. How they remember people and events. And I think about those kids who might stop by an Obama monument many White Houses from now. They may not see it at first, but if they look closely, somewhere in the smallest veins of the granite will be the people who worked there, winged it there, laughed there, fell in love there, cried there, and served there.
On January 17, 2017, as the iron gates locked into place behind me for the final time, my blue badge gone, I thought back to Antoinette’s overly earnest, corny-as-hell daily goodbye: “It’s been a pleasure serving the American people with you.”
Yes, it had been.
* * *
I. On this day, my parents were in Cuba. They would call me that night, trying to get information on the news that was still to come.
II. Antoinette had moved from Lower Press to Upper Press.
III. Brian found out about our illicit use of the Rose Garden only when they brought the photo to the Oval to be signed.
EPILOGUE
* * *
. . . Of the End
She’s not going to get there.
A lump formed in my throat the instant I heard it, but I was determined not to cry.
“Okay, then . . .”
The West Wing was emptying out. And I thought it was time to leave. The party was over. I departed the White House grounds knowing that walking into work would never be the same but unwilling to grapple with what it all meant at midnight. A crowd had gathered on Pennsylvania Avenue. Somebody asked me if they had called it. I yelled back “No!” and kept moving.
Typically, I’ll check my work phone ten times in the brief time it takes to walk home, but I had nothing to look at this night. Both phones dead. I peered creepily into somebody’s window from the sidewalk to see if the worst had become official, but all I could make out were the blues and too much red of election night coverage. I kept moving. It was unseasonably warm. I slapped myself hard on the cheek, which I regretted immediately as cliché.
I was relieved to find that the election had not been called when I arrived home, the campaign granted a stay of execution. Stephanie, still in her Hillary T-shirt, and I watched John Podesta, who used to pop in and out of Upper Press often, walk into frame. He asked the group of thousands, assembled under the glass ceiling of Manhattan’s Jacob Javits Center, to head home.
The day after the election, we woke up to a gloomy, rainy day. It was fitting, but also a bit much—like we were living a movie with a lazy script. In the basement of the West Wing, I heard a White House aide plead facetiously with a counterterrorism staffer, “Please tell me it was the Russians.”
I wasn’t ready for the gallows humor and remained stoic until my mom called. She had won big the night before, but I heard her crying on the other line. Aubrey had just called her on the way to preschool. Aubrey liked to imitate Trump by shouting “Blah blah-blah blah-blah!” She had seized on his lack of substance and took her imitation to anyone who would listen. She even delivered the spot-on impression to the Clintons, after asking about the trash in the park. They were delighted. “We’ve got to get you on TV,” President Clinton said with a smile.
I loved the Trump impression, but I was ready to b
e done with it, to move on from his candidacy. So was Aubrey, who had wanted to talk to her grandmother as soon as she heard the news about Donald. She was confused and upset, but, still, she was sure it would be okay: “Hillary can win next year, right?”
She thought that in part a presidential race was like a regular race. “Hillary just ran a little slower than Donald last night.”
I choked back tears thinking of the eternal hope and brightness of a child, as I filtered into Josh’s office with dozens of other shell-shocked staffers. We were back where we had begun to celebrate the night before.
Jen Psaki reminded us of the important work that lay ahead, and Cody previewed the remarks he had worked on with the president, to be delivered in the Cabinet Room. The president’s assistant, Ferial, dropped in and asked for Josh. A moment later, she was back:
“The president would like to see all of you in the Oval Office.”
I’ve given countless White House tours for friends and family, most of whom comment on how small and cramped everything is. Not so with the Oval, where the drab carpet of the West Wing gives way to beautiful hardwood and a rug with the president’s favorite quotes emblazoned along the outer edge. The light is brilliant, crisp.
Our group of communications staffers, from the press secretary down to the media monitor, made our way in. For some, this was their first time in the Oval Office. We spread out along the edge of the room, and I took my place between Kennedy’s “No Problem of Human Destiny Is Beyond Human Beings” and Roosevelt’s “The Welfare of Each of Us Is Dependent Fundamentally Upon the Welfare of All of Us.” President Obama began to speak, but staffers kept filtering in; he punctured the tension, calling the procession “like a clown car.” He and the vice president stood in front of the Resolute desk. The president started again. He talked about hope and about the importance of doing things the right way—now more than ever. “This is not the apocalypse,” he said. The vice president shook his head.
I had seen this format before, even set it up myself sometimes. The president speaking, with the vice president at his side, reaffirming with a smile or underscoring the importance of the moment with a nod. We used it to powerful effect throughout the presidency. I hadn’t ever been its intended audience, though.
This is not the apocalypse.
At this point, I broke down. This was not the poised sniffling that the moment called for. I was full-blown ugly crying in the Oval Office as the president gave us a pep talk.
I was upset for my niece, who didn’t understand that Hillary couldn’t win in a year. And for my mom, who worked so hard on Hillary’s behalf. And for my wife, who wore her Hillary shirt to work and around town. And for my nana, who thought she would finally see a woman president. I was selfishly upset for myself. This wasn’t how it was supposed to end.
I hadn’t even begun to think about the people across the country—the vulnerable, the disadvantaged, the different—for whom a Trump presidency could have real, tangible effects. Still, the president highlighted something that Ben Rhodes, who was standing off to the side, had emailed him when the outcome seemed clear the night before. “History doesn’t move in a straight line. It zigs and zags.”
In the Oval, desperately trying to compose myself in front of my Obama family, this was a hard zag.
I had to turn away and try to get it together. The president reminded us that most of the folks in the room were young and that this was just our “first rodeo”—that we had known only winning, but hope is called for most in our losses. Then he said that he didn’t want to do the televised speech in the Cabinet Room. He looked to the windows; the rain had stopped. “Look, it’s sunny out,” he said, and suggested he give the speech in the Rose Garden. It was more optimistic. He asked if we agreed.
Yes, we did.
Photo courtesy of Doug Mills
Me, mildly confused, in front of Air Force One during the 2012 campaign. Surely in a swing state.
Photo by Pete Souza courtesy of White House
Pretty clear in hindsight that he can tell I don’t know what I’m talking about. Note the paper on the Resolute desk: the NCAA basketball tournament bracket.
Photo courtesy of Lawrence Jackson
A final photo of the Upper Press crew in Josh’s office on the day before JPalm left to help run Hillary Clinton’s campaign. From left to right: Howli, me, Desiree, Peter, Jennifer Palmieri, Crystal, Antoinette, and Josh Earnest.
Photo courtesy of author
Part of the later-term Upper Press crew at Camp David. From left to right: Liz Allen, me, Peter, Jen Psaki, Courtney, and Sarah.
Photo courtesy of White House
Playing with Obama the day after Thanksgiving 2016 at Joint Base Andrews.
Photo by Pete Souza courtesy of White House
Prepping President Obama for his episode with Jerry Seinfeld for Comedians in Cars Getting Coffee.
Photo courtesy of Doug Mills
Trailing Marine One through the air in Nighthawk 4.
Photo courtesy of author
From left to right: Peter, me, Desiree, Bill Murray, Liz Allen, and Josh Earnest.
Photo courtesy of author
Drake stopped by and took over my desk. Nowadays, you can call him on his cell phone.
Photo courtesy of Pablo Martinez Monsivais
My memory of this was that I made Conan laugh. My memory was very wrong.
Photo courtesy of author
Bugged Russian teddy bear given to me at the G20 in St. Petersburg. His eyes kind of give away that he’s hiding something.
Photo courtesy of author
The infamous horse photo. No comment.
Photo courtesy of author
Bo rummaging through Upper Press for food. Also, my desk in a familiar state: a mess.
Photo courtesy of Evan Vucci
Proposing to Stephanie in the Rose Garden (she said yes).
Photo courtesy of Stephanie Cunnane
My nana and me just after finishing my time in the Obama White House. She’d just relayed one of her favorite mottos to me: “Take no prisoners; have no mercy.”
Photo courtesy of White House
My niece Aubrey going in for a hug just after saying, “I love you, Barack Obama.”
Photo courtesy of Peter Velz
Obama cruising by the Oval Office.
Photo courtesy of Peter Velz
Obama steps out of “The Beast” after showing Jerry his ride.
Photo by Pete Souza courtesy of White House
The president looks at me quizzically as I explain the surprise Mother’s Day calls. Also, my wife tells me you’re not supposed to wear black shoes with a blue suit.
Photo courtesy of White House
The president provides perspective—and hope—the morning after the 2016 election. You can see me above the vice president’s head.
Photo courtesy of White House
My family stands with Obama in the Oval Office for a departure photo near the end of the second term. From left to right: dad, Stephanie, me, 44, mom, Harry, Alex. Lots of buttoned blue suits.
Acknowledgments
Writing a memoir when you’re twenty-nine is a little absurd. So first, thank you David Larabell, Jonas Brooks, and everybody at CAA for taking this idea seriously from the start, and believing I had a story to tell.
Thank you to Gallery Books for, well, buying the story. But more important, to the team that made West Winging It an actual thing. Natasha Simons, you are a superb editor and you made the book better. I also thank Jen Bergstrom, Jen Robinson, Hannah Brown, Jean Anne Rose, Theresa Dooley, Monica Oluwek, Alexandre Su, and Lisa Litwack.
Thank you to my Obama family: the folks who welcomed me into the fold, who mocked me mercilessly, and who helped make me a better person. Dan and Howli Pfeiffer, Matt Lehrich, Liz Allen, Marie Nesi, Bobby Whithorne, Eric Schulz, Antoinette Rangel, Brian Mosteller, Jeff Tiller, Amy Brundage, Clark Stevens, Hannah Hankins, Desiree Barnes, Crystal Carson, Jen Psaki, Jen Palmieri, Jos
h Earnest, Jay Carney, and Peter Velz (who dealt with more questions from me while writing this book than anybody else).
There are Obama people never mentioned in my book—some of whom I didn’t know well, but whose accomplishments and competence, their own remarkable stories, shaped the way I think about the Obama White House. People such as Deesha Dyer and Gary Lee and Brandon Lepow. Thank you.
Importantly, I thank my family and friends who’ve put up with me and helped me, from my uncle Bob Dean and neighbors Sean and Anne to my cousin Johnny Buonomo. My in-laws, Jim and Debbie Genuardi; Victoria, Owen, and Dan Edwards; and Kevin and Maureen Genuardi, who I’ve bugged about buying this book for months. Thank you to my nana and pop-pop, who play a crucial role in the book and an even more vital role in my own life.