I’m 90 percent sure President Obama was half joking. Still, two months later, on my final POTUS trip, my stomach full of arugula and Brie, I was careful to avoid his eyes. Backstage in Detroit, POTUS went through his usual prespeech routine, shaking hands with the prompter operators and joking with personal aides. Then he stepped onstage to remind a roomful of autoworkers about the time he saved their industry seven years before.
I had written plenty of auto speeches for President Obama. There was nothing especially new in this one. But as POTUS reached his closing paragraph, my eyes filled with tears. I had tried to prepare myself for each milestone: my last set of remarks for the president, my last ride in the motorcade, my last flight on Air Force One. Still, the nostalgia left me reeling. I fled the staff viewing area and found a men’s room. With my left hand, I steadied myself against the sink. With my right, I held all but the first page of my speech.
You’re supposed to be an adult, I reminded myself. And adults don’t cry in front of their boss’s boss.
I pulled it together, took a deep breath, and returned to the hold room to wait. Presidential trips are like that. One moment your fortunes are tied, inextricably, to the most important person on earth. The next moment you’re killing time in someone’s abandoned third-grade classroom or empty office suite. Five minutes passed. Ten minutes. Then a voice rang out from the hall.
“Litt!”
It was POTUS. With his left hand he clutched the first page of my speech, now inscribed with his unmistakable signature. He held his right hand palm up, for a shake.
“You didn’t tell me you were leaving,” he said.
“Well, actually, I’m trying to sneak out.” By my low standards, this was remarkably good banter. The president bantered back.
“You didn’t do a very good job. I caught you.”
He started to ask a question, but one of his aides gestured toward cameras set up for a post-speech interview. “Never mind,” he said. “We’ll talk more on the plane.”
We didn’t, of course. On the flight home, the president was busy being the president, and I was busy eating Cuban picadillo with a fresh side salad and keeping my feelings at bay. It wasn’t until we were about a half hour from Andrews Air Force Base that I heard the phrase “bad weather call.” Not long after that we landed in the snowstorm. Not long after that, we loaded the motorcade only to find every inch of asphalt choked with cars.
And now we’re going nowhere. The light turns red. The motorcade once again grinds to a halt, this time beside a Chick-fil-A. Another metaphor. I’m frustrated and nervous, wondering if anyone has a plan.
On cue, Sarah Palin’s voice pops into my head. She’s always doing this, showing up when my spirits are lowest. It’s like I have a fairy godmother who hates me.
“So,” she asks, “how’s that whole hopey, changey thing workin’ out for ya?”
It’s a line she started using in 2010, when President Obama’s approval ratings were plummeting and the Tea Party was on the rise. And here’s the thing: if you ignore her mocking tone and that annoying dropped G, it’s a good question. I spent the lion’s share of my twenties in Obamaworld. Career-wise, it went well. But more broadly? Like so many people who fell in love with a candidate and then a president, the last eight years have been an emotional roller coaster. Groundbreaking elections marred by midterm shellackings. The exhilaration of passing a health care law followed by the exhaustion of defending it. Our first black president made our union more perfect simply by entering the White House, but a year from now he’ll vacate it for Donald Trump, America’s imperfections personified.
The motorcade keeps skidding and sliding. For twenty miles we veer left and right, one close call after another, until we finally reach the South Lawn. Here, too, I have a routine: get out of the van, walk through the West Wing, head to my office across the street. It’s a trip I’ve made countless times before. It’s also one I will never make again. And as I walk past the Rose Garden, the flagstones of the colonnade pressing against the soles of my leather shoes, Sarah Palin’s question lingers in the January air.
How has it all worked out?
PART ONE
OBAMABOT
1
THE RAPTURE
On January 3, 2008, I pledged my heart and soul to Barack Obama. There was no formal, lovesick declaration. No one tattooed a Hope poster across my chest. Still, my transformation was immediate and all-consuming. One moment I was a typical college senior, barely interested in politics. The next moment I would have done anything, literally anything, for a freshman senator from Illinois.
I was not a likely candidate for conversion. The summer before I began working for Obama I interned at the comedy newspaper The Onion, where my boss wore roller-skate sneakers and sold feminine hygiene products from a kiosk at his desk. It was a dream job. I fetched coffee and did busy work. In exchange, I got to sit in on a writers’ meeting and watch a senior editor come dangerously close to a psychotic break. “We’re a comedy paper, not a stupid paper!” he shouted, before storming out of the room. I had never been part of anything so meaningful.
There was just one problem: I didn’t fit in. As an intern, my biggest responsibilities were proofreading articles and writing jokes about the weather, but the second task kept getting in the way of the first. Each morning, I’d arrive at work and think, Cloudy with a chance of meatballs! I knew it wasn’t funny, but the phrase lodged itself in my head like a mantra, or a tumor. Typos went uncorrected. Run-on sentences ran on.
Cloudy with a chance of meatballs. Cloudy with a chance of meatballs. Cloudy with a chance of meatballs.
This wasn’t just another job. I worshipped The Onion. I grew up in Manhattan, and I’ll never forget the headlines from the issue released a few weeks after 9/11, when I still thought al Qaeda would kill me before I finished tenth grade.
HIJACKERS SURPRISED TO FIND SELVES IN HELL
* * *
NOT KNOWING WHAT TO DO, WOMAN BAKES AMERICAN-FLAG CAKE
In that awful moment, a small, satirical newspaper was everything I loved about my country. Defiant. Proud. Optimistic in spite of everything. The Onion gave me hope I might not die a virgin. What could be more uplifting than that?
But if satire represented the best of America, politics was the worst. My family is a classic American-dream story. My great-grandparents fled Russia to avoid being murdered for their religion. Just two generations later, my parents fled New York City weekends for their country house. I never felt guilty about this. I was raised to believe America rewards hard work. But I was also raised to understand that luck plays a role in even the bootstrappiest success story. The cost of living the dream, I was taught, is the responsibility to expand it for others. It’s a more than fair price.