Kathleen Sebelius’s Daily Show Disaster: Jon Stewart Slams Obamacare Rules

In a cringeworthy appearance last night, the Health and Human Services Secretary crumbled under Jon Stewart’s grilling about Obamacare. Lloyd Grove on why Republicans are going to have a heyday with her answers.

Comedy Central

In politics, it’s better to be lucky than to be talented, brilliant, well-liked or even right. President Obama has been supremely lucky—lucky in his prospects, lucky in his timing, lucky most of all in his enemies.

Once again, he can thank his good fortune that the media-political complex is so obsessed with the federal shutdown and the specter of government default—a catastrophe that most folks believe, according to polls, is the handiwork of Tea Party zealots—that his Health and Human Services Secretary’s devastating Monday night appearance on The Daily Show isn’t getting the attention it might otherwise deserve.

“We’re gonna do a challenge,” Jon Stewart said, pulling out a laptop as he ushered Kathleen Sebelius to the hot seat. “I’m gonna try and download every movie ever made, and you’re gonna try and sign up for Obamacare—and we’ll see which happens first.”

Sebelius, who was spending her day trying to sell and defend the error-prone program, laughed weakly. It was all downhill from there.

Stewart asked Sebelius how many people have signed up for the government-sponsored health insurance mandate since it went live a week ago in a glitch-rich debut.

“I can’t tell you because I don’t know,” she answered, drawing snickers from the studio audience and some mugging from her host.

Stewart repeatedly pressed Sebelius on why businesses are permitted to delay the mandate until a year from now while previously uninsured individuals are required to sign up post haste and start paying premiums during a six-month enrollment period.

Sebelius gave a variety of answers and non-answers, which Stewart made clear he didn’t accept. He offered the theory that maybe businesses are getting a break because they pay lobbyists to tweak the system while ordinary people do not. Sebelius offered that individuals can also delay enrolling; they’ll just have to pay a fine at the end of the year. The audience laughed, and not too kindly. Stewart gave her one of his theatrically baffled looks. “Let me ask you this,” he said sweetly. “Am I a stupid man?”

Not since the sharp-witted satirist addressed the president as “Dude” three years ago during a contentious back and forth about the tepid performance of the economy—obviously a case of Obama’s good luck temporarily running out—has an administration official fared so calamitously on camera.

Mounting an aggressive attack from the left—which has been picked up and run with by conservative websites and media outlets—Stewart picked apart Sebelius’ sales pitch, passionately argued for a government-run single-payer health care system instead of Obamacare’s market-based, federally-administered hybrid, and ended up by suggesting—after she departed the stage—that maybe she had been lying to him.

All that was bad enough, a textbook example of how not to do political messaging, but Sebelius made an even bigger mistake during the extra four minutes of the encounter that was not broadcast on Comedy Central but is available online. After Stewart rose from his chair to croon a refrain from the Republican-endorsed Lee Greenwood anthem, “I’m Proud To Be An American,” Sebelius decided to try her own hand at comedy.

“As you know, we’re facing the end of the Western Civilization by having a market-based strategy,” she declared, deadpan, apparently trying to mine a vein of hilarious sarcasm. “We’re bringing Western Civilization its knees by having a private insurance plan on a website where people pick and choose.”

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Maybe the Republican Party and its allies have bigger fish to fry at the moment—at least until the Oct. 17 debt ceiling deadline—but once the current controversy blows over, I shudder to think what they’ll do with those utterances, to say nothing of the rest of her Daily Show disaster.