And what about me? Did I ever succumb? By definition, I can’t honestly say. Awash in paradox, it’s possible (likely, on some occasions) that I acted like an asshole in ways I still don’t realize. Here’s what I know for sure. On days I didn’t exercise, one beer was rarely sufficient to calm my nerves. More often than I care to admit, I went home and acted bratty until Jacqui felt as stressed as I did. There were even moments, often involving airline customer service, in which I thought without irony, Don’t you know who I am?
Also, like everyone, I aged. No matter how young or old, junior or senior, White House service was measured in dog years. Between ages twenty-four and twenty-eight, my gray hairs went from curiosity to invasive species. The dark circles under my eyes became, essentially, tattoos. It only added insult to injury to hear the wrinkles emerging along my mouth referred to as “smile lines.” I knew plenty of smiley people who didn’t lose sleep trying to describe the budget, or furrow their brows each time they saw a member of Congress on TV. These people had hobbies. They went to brunch. Their mouths were fine.
Of course no one aged more, or more publicly, than POTUS. In 2012, I wrote a joke about how he would look like Morgan Freeman by the end of his second term.
“That’s not even funny,” he said.
Three years later, I could see his point. It wasn’t just the well-documented explosion of gray hair. By 2015, President Obama’s puffy eye circles had their own puffy eye circles. His smile lines appeared to have been carved by glaciers. His fingers seemed more delicate, his skin somehow thinner. To adjust to his aging eyes, speechwriters quietly raised the font size on printed remarks from 24 to 26. Every crisis and decision had become part of him, like rings inside a tree.
So, was it worth it? This, I think, is the essential question facing anyone with a tough job, and President Obama’s was the toughest of all. He had chosen his profession with eyes open. He hadn’t taken nearly as much risk as, say, a fighter pilot or marine. Still, the sacrifices were real.
And at the beginning of his second-to-last summer in office, it was also entirely possible they would be in vain. The unique appeal of Obama—what separated him not just from other politicians, but from other Democrats—was the promise that government could do more than fix problems. Government could be a vehicle for our common aspirations. Government could tackle age-old challenges, leaving our country fundamentally better than before.
This is why so much of POTUS’s legacy came down to two persistent stains on the nation’s soul. The defining policy issue of the Obama years was health care. The defining moral issue was race. And in June 2015, on each of these issues, progress was very much in doubt.
With health care, doubt came in the form of a lawsuit. By now, large parts of the Affordable Care Act were succeeding. The uninsured rate had never been lower. The cost of medical care was growing more slowly than before. Obamacare had survived a Supreme Court challenge, a government shutdown, and approximately a gajillion votes for repeal.
But the Holy Warriors refused to surrender. Undaunted, they tried another legal challenge, this time on even shakier ground. It was a truly silly argument—their case hinged on the lawmaking equivalent of a typo—and we figured the Supreme Court would never agree to hear it. Then the Supreme Court agreed to hear it. We began to sweat.
The second issue, race, was far more complicated. For obvious reasons, I don’t claim to be an authority on the subject. But I am the world’s foremost expert in pitching the following joke:
“No matter what else happens, I think there’s a good chance I’ll go down in history as America’s first black president.”
Year after year I tried to add this line to a monologue, and while it wasn’t my finest work, I don’t think that’s why it got cut. In Obamaworld, there was always the nagging fear that the president’s racial legacy would be defined by his skin color, his election, and nothing else. It was the kind of thing you didn’t joke about.
Yet halfway through 2015, that worst-case scenario also appeared to be the most likely one. Deaths of African Americans at the hands of police brought decades of simmering tension to a boil. Black Lives Matter, a movement led by a new generation of civil rights activists, was rightly dissatisfied with the pace of change. After each tragedy came a wave of protests. Occasionally there were riots. Always there was the hope that this nightmare would be the last. But it never was. The tragedies piled up.
Then came Charleston. On June 17, a white, mop-topped twenty-one-year-old walked into a black church and, after taking part in Bible study, shot nine people dead. The killer’s name was Dylann Roof, and he didn’t choose his target at random. He hoped to start a race war or, even better, convince America a race war had already begun.
It seemed entirely possible he would succeed, setting off a perpetual motion machine of chaos, violence, and hate. And even if Roof’s act of terror failed to metastasize, there was no question Charleston left America exhausted and depressed. On the next evening’s Daily Show, Jon Stewart told his audience he was out of jokes. Instead, he delivered a deeply pessimistic tirade.
“We still won’t do jack shit,” he said. “Yeah. That’s us.”
The following Monday, a sense of gloom and uncertainty hung over the country. The White House was no exception. It was quite possible that, sometime before the week was out, the Supreme Court would rob millions of their health care. It was certain that on Friday the president would go to Charleston, where even the consoler in chief seemed no match for the cold logic of despair. Our string of fourth-quarter wins suddenly felt less exhilarating. Would President Obama’s faith in America prove unfounded? Would his legacy, and ours, fall apart? No one knew.
And then, in a period of less than forty-eight hours, everything was answered.
IT STARTED ON THURSDAY, WITH A RULING BY THE SUPREME COURT. Lots of people think that White House aides get advance notice of these decisions. Surely someone knows a guy who knows a guy. No, they don’t. Instead, judgments are unveiled like Oscar winners, a tradition both cruel and unusual for staffers who spend every waking hour creating the illusion of control. Imagine a careful, calculating poker player pausing halfway through a hand for an interlude of Russian roulette. That’s what decision days are like.
In June 2015, these tense moments were even tenser than usual. At approximately 9:55 A.M., as the justices prepared to release their rulings, the entire building stopped whatever it was doing. The minutes ticked down, then the seconds. By now Jacqui was covered through her employer, so her insurance didn’t hang in the balance. But for Zoe Lihn and millions like her, the next moment could be the most important of their lives. I bit my cheek nervously. My feet twitched.
And then, at 10 A.M., an anticlimax. The court would rule on something other than Obamacare. My adrenaline still pumping, I’d return to work.