Thanks, Obama: My Hopey, Changey White House Years

And they didn’t just watch. They took action. Overnight, traffic to Healthcare.gov jumped 40 percent. In the two weeks that followed the episode’s March 11 release, the young and healthy came out of the woodwork to sign up.

Back in 2013, before Healthcare.gov, the nonpartisan Congressional Budget Office predicted seven million people would purchase insurance through Obamacare. After the site’s disastrous launch, the law’s critics confidently gloated that this projection would be way off. They were right. By mid-April, eight million people had signed up.

On April 17, President Obama held a press conference to trumpet the good news, and Cody assigned me to write what’s known as the topper—brief, prepared remarks before the first question is asked. I was thrilled. I couldn’t wait to help POTUS tell our comeback story.

Yet when I arrived outside the Oval Office a few minutes before the presser, the president didn’t appear excited. In fact, he looked downright glum. As usual before a public appearance, he was bantering, this time with press secretary Jay Carney. But the bouncy energy he displayed before big rallies was missing. At one point, the subject turned to weekend plans.

“Golfing again?” Jay joked. GOP frenzy over the president’s weekly eighteen holes renewed themselves like clockwork each spring, a blooming crocus of outrage. But President Obama didn’t look amused. He looked weary.

“Jay,” he said, “that’s the only time I get to go outside.”

It was only once we arrived in the briefing room that I understood why POTUS might feel deflated. On television, presidents at press conferences appear larger than life. In person they look like goldfish in a bowl. The James S. Brady Press Briefing Room—which holds forty-nine seated reporters—is only slightly bigger than your average American garage. The stage has all the height and majesty of a shipping pallet. President Obama wasn’t commanding his audience. He was surrounded by it.

Before I continue, I should clarify something: I don’t think most members of the traditional White House press corps are biased toward a political party. That said, they are definitely out to get the president. It’s only natural. Every reporter wants to be Woodward and Bernstein. Setting their sights on anyone but POTUS would be like Captain Ahab chasing a guppy across the high seas.

Along with this common dream—uncovering the next Watergate—reporters share a tendency to herd like wildebeests around a single dramatic arc. “What’s the story here?” they ask, as though narratives are distant planets to be discovered rather than frameworks they create. As a consumer of news, I empathize. I count on journalists to help me decide what matters and what does not. But the danger arises when facts start to fit the narrative and not the other way around. Combine reporters’ desire to congeal around a story line with their innate distrust of the powerful, and a presidential comeback is hard to stage.

Still, I was confident that our Obamacare news could pull it off. Imagine if, after its brush with the iceberg, the Titanic had not just stayed afloat but crossed the Atlantic ahead of schedule. That’s what had just happened to POTUS’s top domestic priority. Surely we could all agree this was a game changer.

Well, no. We couldn’t. The eight million new signups, touted so enthusiastically in the president’s topper, were almost completely ignored once the reporters’ questions began.

When will your health care law become popular?

Can you finally fix what’s wrong with it?

Will Democrats embrace it on the campaign trail?

These were not unreasonable things to ask. What was unreasonable was the set of assumptions behind them. With the early failure of Healthcare.gov, the narrative had reached its “floundering president” chapter. No amount of evidence could turn the page.

PRESIDENT OBAMA HAD A TERM FOR BEING STUCK IN THESE CYCLES of negative news coverage. He called it being “in the barrel,” and he treated it the way kindergarten teachers treat an epidemic of head lice. Deeply unpleasant. Happens once or twice a year. Eventually goes away.

I was less certain. I still worried that Americans saw the Healthcare.gov debacle as a kind of infidelity, one they had not yet decided to forgive.

As the 2014 Correspondents’ Dinner approached, I didn’t think one night of comedy could fix everything. That said, I thought it could help. If POTUS was ambitious in his material and flawless in his delivery, voters might feel the old spark rekindled. Reporters might decide the narrative wasn’t so set after all. As the joke-writing process began, our task seemed clear. Take big swings.

And not just at our opponents. By making fun of our own low moments, we could show the world we had moved on. This concept—self-deprecation—is one that a surprising number of important people fail to grasp. I know far too many speechwriters who have lived through some version of the following exchange.

POLITICIAN (doing his best cool dad impression): I love making fun of myself! Whadaya got?

SPEECHWRITER (nervous): Well, I was thinking we could joke about the idea that you’re kind of a diva?

POLITICIAN (recipient of a sudden personality transplant): What? A diva? Why would anyone find that funny?

If you ever find yourself on the receiving end of this question, here is my advice: Do not answer it! Fake a seizure. Play dead. Flee the country. Whatever you do, don’t open your mouth.

Where self-deprecation was concerned, President Obama’s joke writers were lucky. While I can’t say he truly enjoyed making fun of himself, he understood its value. No less important, he had a sense of gallows humor. A friend of mine who worked in the National Economic Council was first introduced to POTUS at the end of 2013.

“This is David Edelman,” said my friend’s boss. “He’s working on tech issues.”

Without missing a beat, POTUS eyed him skeptically.

“You’re not the guy who designed my website, are you?”

There was another reason the president liked making fun of himself: it earned him the right to mock people who genuinely pissed him off. In our first Oval Office meeting for the 2014 dinner, our draft included a full page of one-liners about Healthcare.gov. In exchange, we got to make fun of everyone from Mitch McConnell to the right-wing billionaire Koch brothers to the hosts of Fox & Friends.

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