Thanks, Obama Read online

  You know how when you’re playing Minesweeper? And at first you just can’t get the hang of it, no matter how hard you try? But then everything begins making sense, even on the highest difficulty setting, and the goal you never even admitted having is suddenly within your reach?

  It was kind of like that.

  A few days later, feeling slightly stuffy in my suit, I made my way to a small kiosk a few blocks from my firm’s office. “Can I help you?” asked a Secret Service agent, from behind his pane of bulletproof glass.

  “Yes, you can,” I told him. And then, just because I could, I added something.

  “I have an appointment at the White House.”

  3

  CLEARED TO WORK

  The intern escorting me to my interview had the nervous formality of a bar mitzvah boy. Mike Strautmanis, Valerie Jarrett’s chief of staff, was clearly more comfortable in his skin. Above his office fireplace, instead of a portrait or plaque, he kept a pair of signed Yao Ming sneakers. Next to his conference table he had installed one of those putting-practice machines that spits the ball back when you make a shot. A different kind of high-ranking official might have held it against me when I mispronounced his name, rhyming the first syllable with trout instead of trot. Straut let it slide.

  I had spent days rehearsing my answers to interview questions. Favorite Obama speech. Greatest strength. Greatest weakness (that was sneakily also my greatest strength). But Straut didn’t ask me any of that. Instead, he rose from his chair, towering over me as he headed for the door.

  “Tell you what,” he said. “I’m leaving for an hour. Why don’t you write a two-page speech for a breakfast roundtable with CEOs. Then I’ll take a look.”

  This was madness. At my firm, I’d have at least a week for a two-pager. I’d also be given guidance on what to write. But with the clock ticking, there was no time to complain. I dove in, a white-collar MacGyver defusing a rhetorical bomb.

  All right, David, think. Quotes from the president. Random facts about the economy. Praise for American innovation. It just might work.

  I finished my draft mere seconds before Straut returned. While he read through it, the bar mitzvah boy intern brought me to a greasy, ground-floor cafeteria known as Ike’s. I ordered a ham and cheese on a thick sub roll, and ate it with trembling fingers.

  At least I could take comfort in being finished. In the worst-case scenario, I could always say I had written a speech in the White House. In the best-case scenario, I would return a few days later for a follow-up with Ms. Jarrett herself.

  “Tell you what,” said Straut, when I got back to his office. “Let’s see if she’s free right now.”

  “Sounds great!” I replied.

  But I didn’t mean it. As far as I was concerned, a meeting with Valerie Jarrett—Senior Advisor to the President, Head of the Office of Public Engagement and Intergovernmental Affairs—required the sort of preparation usually accompanied by a montage. Valerie was one of the most influential people in the White House. This meant she was one of the most influential people in the world. Even her lengthy Wikipedia page made her appear both glamorous and terrifying, a cross between Anna Wintour and the Sphinx.

  Which is why I was surprised when our meeting was quick, painless, and disarmingly low key. Valerie was warm and friendly, albeit in an official, don’t-forget-that-I-could-squash-you sort of way. She asked about my experience. I told her I was excited about the opportunity. Every so often she nodded thoughtfully, and ten minutes later we were done. Only after I left her office, and Straut began asking me about salary, did I realize Jon Favreau hadn’t been exaggerating. There really were no other candidates. The job was mine.

  When strolling down memory lane, it’s always tempting to spackle on a layer of retroactive dignity. As I considered my good fortune, John F. Kennedy’s words echoed through my heart. “Ask not what your country can do for you,” I told myself, thanking God for the gift of freedom.

  Nonsense. I rushed back to my apartment, ripped off my suit, and jumped up and down in my underwear. I fist-pumped. I hollered the word holy, followed by every obscenity I knew. Then I immediately started calling people.

  I SHOULD HAVE BEEN MORE CAUTIOUS. GETTING A JOB OFFER FROM the White House is like getting a marriage proposal from Tom Cruise: there’s a lot of paperwork before the deal is sealed. The due diligence began before my interview was even over, when Straut asked if there was anything I hadn’t told him yet.

  “It’s better if you let us know,” he said. His tone was part friend, part hitman. “We’ve ‘unhired’ people before.” With these words, the background check began.

  First came the federal investigation. Friends and family were interrogated by the FBI, their stories cross-checked for inconsistencies and gaps. Next was a form called the SF-86, a 127-page Godzilla of questionnaires. I wrote down every address I’d ever lived at. I listed every job I’d ever held. Some questions were fairly standard: Had I been convicted of a crime? Had I been delinquent on my debts? But others reflected a curious faith in the power of capital letters, and the honesty of America’s foes.

  “Are you now or have you EVER been a member of an organization dedicated to terrorism?”

  “Have you EVER knowingly engaged in activities designed to overthrow the U.S. government by force?”

  Most of the SF-86 was nerve-racking without being truly scary. It’s the feeling you get when you go through airport security and a tiny part of you wonders if you packed a bomb. For Democrats my age, however, there was one frightening exception: drugs. It used to be that any substance use whatsoever was an automatic deal breaker for federal jobs. That’s no longer the case. But plenty of unwritten rules still apply, and in 2011 they were the subject of a churning rumor mill among the young people of Washington, D.C.

  As long as it was just in college.

  As long as it wasn’t cocaine.

  As long as it happened in Amsterdam.

  As long as you didn’t deal.

  The system could be cruel. In 2009, a West Wing Writers associate named Tom was hired by a cabinet department. On his SF-86, he wrote that he had “regularly” used marijuana in college. This was a mistake. The way Tom explained it, a federal investigator consulted some dusty chart from the Reefer Madness era. Failing to find an official definition of regularly, he had substituted habitually. According to the chart, habitually meant weekly. According to the chart, weekly meant addicted.

  If Tom had checked into rehab and kicked his nonexistent habit, he might have stood a chance. Instead, by decree of the United States government, he was both drug addled and unreformed. Application denied. I arrived at West Wing Writers just as Tom began appealing his case. He used dictation software, so for an entire week I could hear what sounded like a forced confession being recorded down the hall.

  “On . . . March . . . twelfth . . . 1999 . . . I . . . hit . . . my . . . roommate’s . . . bong.”

  Determined to avoid Tom’s fate, I got specific. After some back-of-the-envelope math, I listed thirty instances of undergraduate marijuana use, plus one experience with mushrooms I made clear I hadn’t enjoyed. Afterward, I proudly shared my numbers with a friend who worked for the National Security Council.

  “Thirty?! You should’ve told them less than ten!”

  While the FBI was making sure I wasn’t a threat, White House lawyers were making sure I wasn’t an embarrassment. I write these words during the early days of the Trump presidency, when rejecting unsavory applicants seems as quaint and old-timey as canning your own peaches. But in the olden days of a few years ago, the vetting process struck fear into our hearts.

  Vetting wasn’t entirely subjective. If you were like some of my Yale classmates, ducking out of photos at parties so you could one day run for office unblemished, you would probably pass vet. If you enjoyed tweeting about female anatomy or spinning records under the stage name “DJ White Power,” you probably would not. If you were like me, however, you found yourself in purgatory. Lindsey
, an associate with the White House Counsel’s Office, called me for a friendly interrogation, but I had no idea who she was calling next. Were exes fair game? What about the old, deeply regrettable stand-up routines from my high school talent shows?

  I was told my application had been prioritized, but even so it took forever. One week I was asked to confirm some personal information. The next week I was invited to the Interior Department to pee in a cup. Throughout March I was a contestant on a federally run reality show, bouncing between challenges, unsure whether I’d be eliminated or handed the final rose. Each day my heart pounded as I scanned my inbox. Had something gone wrong with my urine sample? Had the vetters learned about the month in college when I paired thrift-store blazers with Looney Tunes pajamas and was certain I had started a trend?

  Finally, on March 30, 2011, I got an e-mail from Alex, Straut’s assistant. I was twenty-four years old. Most of my proudest achievements in life still fell under the category of “overcomplicated pranks.” But starting April 1, I was cleared to work in the White House.

  MY FIRST WEEK AT WORK, I PUT A FULL CUP OF COFFEE THROUGH THE X-ray machine by the security scanner. It emerged a few seconds later, empty and on its side. “Not a lot of metal in that,” sighed the Secret Service agent on duty, looking for a towel. “Just a thought, for next time.” I could practically see him add me to his Do Not Save list.

  I had not expected this sort of thing to happen. I guess I thought walking through the White House gates instantly makes you better, stronger, and more capable than before. It doesn’t. While my job was more exciting, the rest of me remained fundamentally unimproved.

  This was grossly unfair. Every day, my unchanged abilities were pitted against drastically heightened expectations. Just a few months earlier, for example, I had panicked at the idea of a weekly roommate check-in meeting to discuss the chore chart. Now, with Valerie set to speak on international women’s issues, I was supposed to bring together a half dozen experts from the National Security Council staff.

  What made this meeting particularly frightening was that it included Samantha Power, the president’s top advisor on human rights. At forty-one years old, she already had a degree from Harvard Law, a Pulitzer Prize, and years of experience on the White House senior staff. Far smarter people than I had been exposed as morons merely by her presence. When the big moment arrived, I nervously made my way to a spacious NSC office suite. Then I opened the door, certain one of the greatest foreign-policy minds of her generation was about to reduce me to intellectual rubble.

  But Samantha Power was running behind schedule. This was a golden opportunity. If I could win over lower-ranking staffers, I’d have allies in the room when the president’s advisor arrived. A half dozen of us pulled chairs into a circle. I did my best to turn on the charm. With a shock of satisfaction, I realized it was working. I was making small talk! I was fitting in! Everyone was smiling broadly when, too late, I realized I already knew the stony-faced policy savant sitting directly to my right.

  “Funny story,” said Richard, when his turn came to introduce himself. “David and I met years ago. I was actually his teaching assistant in college.” At this, another staffer, one about twice my age, saw a chance for some lighthearted fun.

  “So, was he a good student?”

  I will never forgive Richard for answering honestly. “You know,” he said, eyebrows arching like an Us Weekly photographer seated next to Lindsay Lohan on a flight, “he seemed kind of bright. But I always got the feeling he didn’t want to be there. He never really applied himself.”

  At that exact moment, as six get-to-know-you smiles turned to frowns, Samantha Power walked in. I tried to apply myself. I really did. But it was hopeless. Each time I asked for details, or failed to grasp a point, I was met with a half dozen disappointed stares.

  The disapproval of my former teaching assistant I could live with. The disapproval of my new boss was something I hoped to avoid. This was easier said than done, as Valerie Jarrett’s superpower was the ability to ask the one question for which I had forgotten to prepare. Before taking my seat at the burnished wood conference table in her West Wing office, I’d research everything: the size of the crowd, the name of the introducer, the exact length of the remarks.

  “So,” she’d begin, “who’s speaking after me?” I don’t know how she did it. This happened every time.

  It was moments like these—plus her habit of looking at you like a goldfish she appreciated but wouldn’t be heartbroken to flush—that accounted for Valerie’s fearsome reputation. “She expects her staff to work as hard as she does” was the line staffers often used. In Washington, this is typically a euphemism for “harasses interns” or “once threw a stapler at the scheduler’s head,” but in Valerie’s case it was true. In 1991, she had interviewed a young woman named Michelle Robinson for a job in Chicago’s city hall. Not long after, she was introduced to Michelle’s fiancé, a young lawyer named Barack.

  The Obamas had been family ever since. More than nearly anyone, Valerie knew how improbable their journey had been. She was determined not to squander a single moment. She demanded the same determination from everyone she employed.

  Valerie never told me this directly, but I also came to believe she saw herself as a custodian of the president’s conscience. As senior advisor, she served not just the middle-aged politician in the Oval Office, but the young idealist she had met two decades before. Ending “Don’t Ask, Don’t Tell.” Fighting inner-city poverty. Opening a gender-neutral White House bathroom. When something fell under the category of “not necessarily great politics, but the right thing to do,” it was often Valerie leading the charge.

  This combination of intense loyalty and unabashed progressivism made my new boss a favorite target. The mouthpiece of the real POTUS, Comrade Valerie Jarrettikov! It wasn’t just Internet trolls who despised her. The mere mention of her name could derange even the most polished member of the GOP elite. “She seems to have her tentacles into every issue and every topic,” declared Utah congressman Jason Chaffetz, as though Ursula from The Little Mermaid had taken up residence in the West Wing.

  But if there was any theft of voices, or abuse of poor unfortunate souls, I never saw it. Valerie’s portfolio was broad because all senior advisors’ portfolios are broad. Involving herself in a wide variety of issues—as both advocate and enforcer—was the essence of her job. And in April 2011, my first month at the White House, those roles had never been more critical. The unemployment rate was nearly 9 percent. Household incomes were going down instead of up. With Election Day less than two years away, there was zero margin for error, and no room for careless mistakes.

  This was especially true for the youngest members of the staff. The small inner circle responsible for President Obama’s rise was not about to let someone born after the first Ghostbusters be responsible for his fall. At each semester’s orientation, Straut lulled new interns into a false sense of security with talk of friendships and personal growth. Then, without warning, he lowered his voice.

  “Let me be absolutely clear,” he said. Too late, the interns realized their teddy bear had become a grizzly. “If you do something stupid and end up on the front page of the Post, you will be out of here immediately. I will not ask for your side of the story. I will not give you a second chance. I will not feel sorry for you. In fact, I will never think about you ever again.”

  You could practically hear the sound of hearts sliding into throats.

  I was the only speechwriter at these meetings. Most of Valerie’s employees in the Office of Public Engagement (OPE, for short) were “liaisons,” professional extroverts each responsible for a slice of the Obama coalition. Young people, African Americans, Hispanics, Jews, state legislators, enviromentalists: an eager young person was assigned to them all. Where other offices thrived on gallows humor, our corner of the White House buzzed with earnest optimism.

  “We put the OPE in HOPE!” my coworkers wrote in e-mails, without any trace of
irony whatsoever.

  I also attended meetings of the POTUS speechwriting team, where, to my relief, sarcasm thrived. Still, I wondered if Jon Favreau would welcome me in. Thanks to his youth, and the quality of his work, President Obama’s twenty-nine-year-old chief speechwriter had become something of a local celebrity. He dated Hollywood actresses. Gawker posted pictures of him playing beer pong without his shirt. I was no good at beer pong. I couldn’t begin to imagine a scenario in which gossip blogs clamored for my shirtless pics. I worried that Jon and I might not get along.

  What I hadn’t realized was that, above all else, Favs was a prodigy. Speechwriters, even great ones, tend to lead either from the head or heart. I was a head-first writer, connecting logical dots and only later adding emotions. Heart-first people went the other way around. Favs was the only true switch-hitter I ever met. His writing was both lyrical and well organized, arcing between timeless values and everyday concerns with astounding ease and grace.

  Perhaps because he possessed innate talent, Favs tended to separate people into two categories: those who had it and those who did not. I was lucky enough to be lumped into the haves. From the day I arrived he acted as if, all evidence to the contrary, his team benefited from having me around.

  “So, is it amazing?” friends would ask.

  Of course it was amazing. Sometimes Kathy, Valerie’s assistant, would explain that we needed to reschedule a meeting because Valerie had been called into the Oval. She said this casually, as though her boss had been put on hold with the cable company and not summoned by the leader of the free world. Other times I would watch Favs and the POTUS speechwriters spitball lines for a set of remarks. A few days later, I would see those exact same lines on the front page of the New York Times. It was unbelievable. I felt like Cinderella at the ball.

  Left unmentioned was that I also felt like Cinderella before the ball. I had never worked so hard in my life. In the speechwriting world, “holding the pen” means bearing responsibility for a set of remarks. My first week at the White House, I held the pen on seven speeches in five days. It was not uncommon for me to edit a single speech four times in an eight-hour span.