The two cases are Sebelius v. Hobby Lobby Stores and Conestoga Wood Specialties Corp. v. Sebelius.
Why the Obama administration could lose
Keep in mind the flow of the arguments in this case. Two for-profit companies have sued, arguing that the contraception mandate violates their religious freedom. So there are two questions: Do these corporations (or their owners) have the right to sue? And if they do, does the mandate violate their religious freedom?
The Justice Department has won a few cases on the first question, but never on the second.
When the Justice Department has lost on the threshold question of corporate rights, it has always lost on the underlying challenge to the contraception mandate. Any time an appeals court decided that a company or its owner could exercise religion, it went on to find that the birth-control mandate at least seems likely to violate that religious freedom. And so the only way the administration has ever won on the mandate itself is to close the door before a court even gets there — which could prove hard to do before the Supreme Court.
Why the challengers could lose
The biggest hurdle for the mandate's challengers is the marquee question of whether they can practice a religion. In one of the cases before the Supreme Court this week, a cabinet-making company called Conestoga challenged the mandate as an affront to the beliefs of its owners, the Hahn family. The 3rd Circuit Court of Appeals, siding with the Justice Department, said the corporation and the people who own it are two different entities.
"Since Conestoga is distinct from the Hahns, the Mandate does not actually require the Hahns to do anything. All responsibility for complying with the Mandate falls on Conestoga," the court wrote.
Another way the administration could lose, but not as badly
Chief Justice John Roberts likes to keep the high court's rulings as narrow as possible on most big issues. He looks for ways to minimize the Court's footprint by avoiding the biggest question — which, in this case, would be whether corporations are protected by the First Amendment's "free exercise" clause.
There's a reasonably clear way for him to do that here: Avoid the question of whether corporations are people, and focus on whether — in these specific cases — people are their corporations.
Both Hobby Lobby and Conestoga are closely held companies, controlled entirely or almost entirely by their owners. The libertarian Cato Institute suggested in a supporting brief that because these two companies are controlled by their owners, the Court could rule in their favor without setting a broader precedent that corporations in general can practice religion.
"Whether a for-profit corporation can exercise religion is an interesting theoretical question. But there is no need to address that theoretical question when legislation regulating a corporation also restricts the religious liberty of the individuals who founded, own, and direct the affairs of that corporation," Cato wrote in its brief.