By Josh Gerstein

As a new round of religion-based challenges to President Barack Obama’s health care law head to the Supreme Court, advocates on both sides of the issue say the administration’s arguments are likely facing a chilly reception.

On Friday, the Obama administration urged the court to reject a plea from an order of nuns who say a provision of Obamacare conflicts with their opposition to birth control.

Already, the Supreme Court is preparing to hear two cases filed by private companies who say contraception provisions in the law violate their firms’ rights to religious freedom.

Together, the cases could recreate a broad left-right coalition on the court that has emerged in the past decade to defend religious rights against alleged government intrusions.

“I wouldn’t be betting on the government winning,” said Michael McConnell, a former federal appeals court judge who favors granting broad religious exemptions. “I would say that the government has an uphill battle.”

A legal expert who has argued for a broad government right to enforce government policies like anti-discrimination laws agrees: the cases — both the immediate battle involving nonprofit nursing homes operated by the Little Sisters of the Poor, and the pending ones featuring for-profit companies Hobby Lobby and Conestoga Wood Specialties — will be tough fights.

“When I look at these cases, I’m not really sure there’s one vote to start with on the side of the government,” said Leslie Griffin, a law professor at the University of Las Vegas.

Experts pointed to two religious freedom cases the court has decided in the past decade, both of which wound up as abject defeats for the government.

In 2006, the court ruled, 8-0, in favor of a New Mexico based church which wanted to use a sacramental tea containing a banned hallucinogen. And last year, the court ruled 9-0 in the case of a Lutheran Church employee that the Constitution bars the government from enforcing employment laws on behalf of anyone the church considers a minister.

At one time, conservatives on the court tended to side with the government in free-exercise fights. “Some of the conservatives — including, especially Justice Scalia…have not been sympathetic to religious exemptions from general laws,” noted Cornell Law Professor Michael Dorf.

Scalia’s 1990 opinion upholding the government’s power to penalize an individual for using peyote — even when used in a religious ritual — triggered a strongly negative political reaction from the right and the left. That led to the passage in 1993 of the Religious Freedom Restoration Act, a federal law that made it tougher for the government to take actions that intrude on religious practice.

The left-right coalition persists to this day and can now be seen from time to time on the high court.

“Democrats like minority religions because they’re minorities and Republicans like them because they’re religions,” Dorf said. “The problem is when you’re not asking for a small exception to a law nobody really cares about anyway, like one forbidding peyote use, but one about people paying their taxes.”

Since the passage of the Religious Freedom Restoration Act, Scalia and some of the other conservative justices have seemed more open to religious claims. “He thinks the Constitution doesn’t require a religious exemption of its own force, but all of them seem perfectly happy to find exemptions based on RFRA,” Dorf added.

With scant indications of how relative newcomers to the court like Elena Kagan think about these issues, some are looking for clues earlier in the justices’ lives and careers.

When Kagan worked in the Clinton White House, she wrote an internal memo decrying the California Supreme Court’s narrow interpretation of the Religious Freedom Restoration Act. She called “quite outrageous” an opinion denying a landlord’s claim that her religious beliefs were burdened by a state law that forced her to rent apartments to unmarried couples. “Taken seriously, this kind of reasoning could strip RFRA of any real meaning,” she warned.

“It does suggest she is not likely to accept the government’s argument that for-profit businesses are categorically unable to raise a free-exercise claim,” McConnell said, while noting that the 1996 memo might not correctly capture her present views on the subject.

McConnell also remembers Kagan being receptive to religious freedom arguments in her days as lawyer and domestic policy adviser for President Bill Clinton. “I do recall that those of us interested in enforcement of RFRA had reason to believe she was our friend and advocate within the White House,” said McConnell, now a professor at Stanford Law School.

Still, some conservatives expect the liberal justices to rally to the defense of the administration and Obamacare.

“My guess is the hard line Kagan took when in the White House Counsel’s Office is not going to hold for the other justices on that side of the bench,” said John Eastman of Chapman Law School. “They’re going to say Hobby Lobby is a corporation and doesn’t have religious freedom rights…I suspect at least four votes on the Supreme Court to take that position.”

Another unknown here is how the justices’ own religious views could color their assessment of the legal issues the cases present. Some analysts said the outcry liberal Catholic columnists like E.J. Dionne and Mark Shields raised last year over the administration’s attempt to force coverage requirements on Catholic-affiliated institutions could influence the way Catholics on the court see the issue — even though the Obama administration has retreated from its initial stand.

“If, with those six Catholic justices on the court, they start with the mindset that of course this is about religious freedom and it would let a Catholic have to provide contraception, that I think will show its way into the opinions,” Griffin said.

Some liberal justices could be receptive to arguments that granting broad religious exemptions, particularly to for-profit employers, could disrupt not only the contraception requirement in Obamacare but vaccinations and other medical procedures. Some employers might seek to use a broad decision to refuse to observe federal-anti discrimination laws or even laws protecting employees from having their pensions raided.

“The stakes in the Hobby Lobby/Conestoga Wood cases in many senses go well beyond Obamacare,” said David Gans of the Constitutional Accountability Center. “That issue will reverberate in a lot of other contexts…These cases could define workplace rights for years to come.”

Some who side with the government in the cases hope that Justice Anthony Kennedy might be receptive to the notion that if the court goes too far in embracing religious freedom rights, that could come at the expense of gays and lesbians — whose rights he defended in the recent same-sex marriage cases — to discrimination in the workplace.

“Opening the door to bosses ending birth control coverage could also open the door to … ending other employee protections and open up discrimination against other classes of people justices like Justice Kennedy have shown they think deserve protection,” said Gretchen Borchelt of the National Women’s Law Center.

“The best chance the government has of winning is if they come up with a really good parade of horribles,” said Dorf. “Eventually you can’t function in a modern economy if you have these kinds of exceptions.”

Most analysts say the issues in the cases now before or headed to the court are different than those in the earlier Obamacare cases, where Chief Justice John Roberts sided with the court’s liberals to uphold the law’s requirement that individuals buy insurance or pay a penalty.

However, there’s a chance that Roberts and other members of the court who are seen as pro-business, like Justice Samuel Alito, might see arguments against allowing a subset of companies out of regulations that apply widely.

“It’s possible Chief Justice Roberts might be the kind of justice who would see that issue,” said Griffin. “It could be: ‘Hobby Lobby, follow the law.’…You could see Roberts pulling off some kind of middle ground compromise where corporate interests are higher.”

In the view of many lawyers, religious groups like the Little Sisters of the Poor — the group of nuns who argued this week that certain requirements could lead to their insurer paying for contraception for employees of the order’s nursing homes — have far stronger arguments for being exempt from provisions of the law than do for-profit business with religious owners.

However, the Obama administration contends that the non-profit groups already have a broad carve-out.

The Justice Department presented a variant on the parade-of-horribles argument in its filing with the court Friday opposing an injunction that would relieve the Little Sisters from having to file a form that the group contends could trigger provision of contraceptives to its employees.

Government lawyers said allowing the Catholic nursing home operators to skip that step could throw a monkey wrench into the procedures the government uses to grant those with religious beliefs a wide array of accommodations.

“It would seemingly mean that the Quaker could not be made to attest to his status as a conscientious objector before being absolved of his military obligations; that the Jewish prisoner could not be required to fill out a form saying he had a religious objection to the consumption of pork before he was provided an alternative meal; and that the Seventh Day Adventist could not be obligated to state that he had a religious objection to working on Saturdays before being relieved of his shift,” Justice Department lawyers wrote.

Whether the justices let Little Sisters off the hook for now or not, that group’s case doesn’t look like an ideal one for the court to consider whether Obamacare does enough to accommodate objections of non-profit religious groups. That’s because Little Sisters uses a church-run insurance plan that wouldn’t be required.

“The not-for-profits, through a better case, are going to make their way to the Supreme Court soon,” Borchelt said.

Dorf said the religious groups’ case, either through Little Sisters or another group, has a better chance of generating a left-right consensus on the court than does the case involving for-profit companies.

“I see a greater likelihood for a non-ideological decision in the Little Sisters case because it’s more likely the liberals will join conservatives in saying it’s a violation of conscience,” he said. The for-profit firms’ cases “could well be 5-4 along normal liberal-conservative lines…This now has a left-right valence to it, as all high-profile legal cases eventually do.”