Thanks, Obama: My Hopey, Changey White House Years

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?

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