Thanks, Obama: My Hopey, Changey White House Years

Not a moment too soon, the president noticed Joe and me share a look of abject horror. Instantly, his attitude changed.

“Guys, what’s going on?”

Silence.

“What?” he snapped.

Remarkably, we still said nothing. But while I remained paralyzed, POTUS’s question snapped Joe to life. Grabbing a towel, he sprinted past me and smothered the diva light.

Once President Obama realized what had happened, he fixed us with a withering look. I prepared myself for a completely justified tirade. But to my surprise, his expression grew weary instead of angry. With a new plastic cover in place, he raced through the taping and into his house.

“Have a great weekend, everyone.”

“Um, you, too, sir.”

I am not saying Barack Obama was a saint, capable of forgiving any trespass. Here’s what I’m suggesting instead: his responsibilities were so great, and he took them so seriously, that his employees’ almost burning his face off barely registered on his list of concerns. There was too much else to worry about. The shutdown had wreaked havoc on our economy. The Holy Warriors were vowing to continue their crusade.

And finally, there was the issue that threatened Obama’s entire presidency, the one that had surely been responsible for his long, somber walk around the South Lawn with his chief of staff. There was no use sugarcoating it. The Obamacare website was a mess.

“JUST VISIT HEALTHCARE.GOV,” SAID POTUS ON OCTOBER 1, THE DAY the online marketplace opened. “There, you can compare insurance plans side by side the same way you’d shop for a plane ticket on Kayak or a TV on Amazon.”

This was a bold claim, belied only by the fact that it wasn’t true. On October 1, Americans could indeed type Healthcare.gov into their browsers. But the idea that anyone could actually use the site was, to put it mildly, a stretch. A lucky handful purchased coverage. For millions more, buying insurance through Obamacare was like returning a defective Kvartal at IKEA multiplied by a Comcast customer service rep. The user interface made airplane cockpits appear straightforward. The pages loaded so slowly they might as well have been written by hand.

That was assuming you could access the site at all. One reporter set out to create an account, and succeeded—after sixty-three tries.

By now, Healthcare.gov’s early faults have been well chronicled. Less commonly understood is the way the website was to Obamacare what LeBron is to the Cleveland Cavaliers. With the star player sidelined, everything else began falling apart.

Nowhere were the consequences more dire than with a simple, ten-word promise: “If you like your plan, you can keep your plan.” Between 2008 and 2013, President Obama made some variant of this pledge approximately three dozen times. This was surprising. Ordinarily, such blanket statements drew a flurry of angry fact-checks.

If you like your plan

Flagging that people with objectively crummy insurance plans may nonetheless like them.

. . . you can keep your plan.

Insurance companies might be forced to drop plans that don’t meet the law’s higher standards. Just flagging.

These caveats were ignored, and in theory shouldn’t have mattered. The Americans at greatest risk of losing insurance had overpriced, subpar plans to begin with. Surely they would welcome the online marketplace with open arms. Imagine learning you could trade in your beat-up ’92 Civic for a brand-new Lexus. You wouldn’t be furious. You’d be thrilled.

With no Healthcare.gov, however, there was no marketplace. The Lexuses were locked inside a labyrinth of buggy code. Meanwhile, the ’92 Civics were being unceremoniously scrapped. Four million Americans were informed their old insurance would soon be taken away.

“If you like your plan” was not a lie, exactly. It was an act of unfounded optimism rather than willful deceit. But when people are terrified about losing health care, such distinctions cease to matter. For the first time ever, President Obama’s credibility with voters began to erode.

This is why the Obamacare rollout was not merely a hiccup or a growing pain. It was a disaster. Imagine if every flight sold through Kayak wound up, unexpectedly, in Mogadishu. Imagine if Amazon accidently began shipping nests of angry hornets to people’s homes.

And here’s where the business world and political world diverge. If Kayak or Amazon are in crisis, it’s a story. If a presidency is in crisis, it’s the story. In the White House, good news is fleeting, and bad news is Groundhog Day. Night after night, Americans heard the exact same report. President Obama’s site wasn’t working. His promises weren’t being kept.

Then there was the most dispiriting news of all: outside the building, people had tried to warn us. In March, a team of McKinsey consultants predicted that Healthcare.gov might not be ready on schedule. In July, the site failed key tests. In August, insurance companies briefed Nancy Pelosi’s office with concerns. In hindsight, I could even recall my own father intervening. “I have this friend in Connecticut,” he told me that summer. “He says these sites are going to be a mess.”

This wasn’t entirely random. My dad happens to be a doctor. But he didn’t work in government. He certainly wasn’t the president of the United States. So what accounted for our massive blind spot? Put another way, how is it that Andy Litt knew Healthcare.gov was going to be a shitshow and Barack Obama did not?

While I’ll never be entirely certain, here’s my guess: no one told POTUS his law was in trouble for the same reason no one told him his head might be set aflame. What we needed was a designated pessimist, someone in charge of sounding the alarm. But role of the naysayer hadn’t been assigned to anyone. As a result, no one spoke up.

In Obamaworld, the typical response to crisis was to circle the wagons, but Healthcare.gov was no typical crisis. Not long after the government reopened, POTUS announced that a cadre of patriotic programmers was being flown in from California. The fate of the second term—the future of hope and change—was no longer in our hands. Only Silicon Valley’s disruptors could save us now.

IN DECEMBER, PRESIDENT OBAMA’S APPROVAL RATINGS FELL TO 40 percent, the same number George W. Bush hit three months after Hurricane Katrina dealt his presidency a mortal blow.

“What’s the mood like over there?” friends asked, less in a spirit of concern than rubbernecking. The Obama White House was imploding. They wanted juicy details. Determined not to give them the satisfaction, I told them we were just fine.

“Everyone’s feeling great!” I promised.

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