On Thursday afternoon, HHS secretary Kathleen Sebelius made a number of unusual requests to insurers selling health plans on the Obamacare exchanges.

Sebelius "strongly encouraged" insurers to pay for prescriptions in January that were covered under policyholders' old plans but not under their new Obamacare plans. She requested that insurers bill some out-of-network care as in-network care. But the most unusual request by far was that insurers allow people to "retroactively" sign up for coverage effective January 1 anytime next month.

"We're encouraging [insurers] to offer retroactive coverage," Michael Hash, director of HHS's office of health reform, told reporters on a Thursday afternoon conference call. "For example, to allow someone who signs up and pays on January 5 to get coverage with a retroactive start date of January the first."

"Many insurers do retroactive coverage in the current market," HHS policy director Chiquita Brooks-Lasure said later on the same call. But health care industry consultant Bob Laszewski says that isn't true.

"I don't know what the hell they're talking about," Laszewski tells THE WEEKLY STANDARD. "I've been in the health insurance business for 40 years. You sign it prospectively, not retrospectively."

Indeed, if people could buy insurance retroactively, why would they buy it when they're healthy? If you could get your medical bills covered from a January 3 car accident by signing up on January 10, there would be no reason to pay a premium in December.

So why would the admininstration make such an unusual request? What seems to be the obvious answer is that the administration is panicked about the fact that Obamacare has canceled the health insurance plans of millions of Americans, and some of those people won't be able to sign up for coverage that starts January 1.

What happens to an American who is uninsured because of Obamacare on January 1 and gets in a car accident on January 3? Will she face bankruptcy? Or will the federal government force the insurer to pay the medical bills or use taxpayer money?

"There's nothing on the table that [the government] can do," says Laszewski. "They have no regulatory or administrative authority to make [insurers] take them. They have no slush funds that I know of."

Laszewski predicts that insurers will agree to retroactively cover people who thought they enrolled in time and can prove it.

"I think if someone has legitimately tried to enroll, and they've got proof that they legitimately tried to enroll, like printing off whatever webpage that says you're enrolled, they're probably going to get fixed retroactively because they made a good faith attempt to enroll," he says. "I would just tell all consumers keep copies of everything."

"I think the real question is when someone claims they made a number of attempts to enroll, they have no evidence of it, then what do you do?" Laszewski asks. "If you're running the insurance company, what would you do?"

It's not clear just how many Americans will experience a gap in insurance coverage because of Obamacare. On Thursday afternoon's HHS press call, one reporter asked: "Is it possible at this point that more people may lose insurance in January than gain it? Is that what's motivating these policy announcements today?"

HHS spokeswoman Julie Bataille went on for nearly two hundred words without answering the question:

"I would remind you that we are, you know, two and a half months into a long six months open enrollment period and we will continue to maintain an aggressive period of outreach and education as we move through that. I think it's also important to remember with the technical improvements that we made to the website, healthcare.gov in particular, that we can now serve 800,000 consumers a day. And I want to be clear as we think about our goals, it's not simply to make sure that we reach millions of Americans and give them access to affordable health care, but also that as we are standing up these marketplaces we make sure to have the right measure of success in them, market by market, with the right mix of individuals who are enrolled. So as we look at the full six-month long open enrollment period, that is really our goal, certainly taking into account the lesson that we've learned from Massachusetts and from the launch of Medicare Part D will all be a part of our ongoing effort."

When the reporter repeated his question, Bataille again refused to answer: "We're confident that millions of Americans will have access to more affordable health coverage than they ever have before."

Insurers privately tell Bob Laszewski that they think more people will have lost insurance by January 1 than the number who have signed up for Obamacare by January 1.

"I was out making some client calls this week with a number of different carriers and they know exactly how many policies they canceled and how many who reupped. And they know how many people have come in through the exchange," says Laszewski. "And I didn't find one of them who thought they were going to be net ahead on January 1. They all think they're going to net behind on January 1. That's where it's trending so far."

So far, at least 4.8 million Americans have received insurance cancellations notices, but Laszewski predicts that the total Obamacare enrollment will be less than half that number on January 1.

"My guess is that we'll have somewhere around a million and a half people signed up for Obamacare on January 1 in the states and in helathcare.gov," he says. The big question then, he adds, is "why have we gone through this whole dislocation of the American health insurance system if only a million and a half to two million buy health insurance?"

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