By: Jennifer Haberkorn

The Obama administration needs to win over at least one conservative Supreme Court justice to save its health care reform law and it’s pulling out the stops to get one.

Administration lawyers have peppered their briefs with citations to opinions written by Anthony Kennedy and Antonin Scalia, they’ve seized on the arguments made by one of Scalia’s most beloved former clerks and their allies in legal circles have talked up how a decision upholding the Affordable Care Act would play into John Roberts’s legacy as chief justice.

A long shot? Maybe, but it’s the only shot the administration has on a court dominated 5-4 by conservatives.

Here’s the pitch they’re making to Kennedy, Roberts and Scalia and the odds that it will work:

Justice Antonin Scalia

He might seem like one of the least likely candidates to support the constitutionality of the individual mandate. But the Obama administration is directly courting Scalia’’s vote.

And because his stamp of approval on the requirement that Americans buy insurance in 2014 would be so surprising, it could also go the furthest in appeasing conservatives who steadfastly oppose the law.

In their defense of the mandate, Obama’s lawyers cite Scalia’s own words in a 2005 case at least five times.

In the Gonzales v. Raich case, Scalia wrote that Congress can regulate a person who wanted to grow legal medicinal marijuana in her home. He said that Congress could do it under the Commerce Clause because the marijuana was “never more than an instant from the interstate market.”

The federal government argues that Congress can regulate the purchase of health insurance in the same way.

Because people can get sick or in an accident, “we are all potentially never more than an instance from the point of consumption of health care, yet it is impossible to predict which of us will need it during any period of time,”” the government wrote in its Supreme Court brief defending the mandate.

The argument could hurt the 26 states and National Federation of Independent Business, which say Congress isn’’t allowed to drag an individual who doesn’t want to buy insurance into the market.

““It’’s certainly not harmful [for the government] to say that the intellectual leader of the conservatives agrees with our legal position here,”” said Brad Joondeph, a Santa Clara University law professor who follows the health litigation at his ACA Litigation Blog.

Plus, it was 6th Circuit Court of Appeals Judge Jeffrey Sutton —– whom in 2009 Scalia called ““one of my former clerks whom I am the most proud of,”” according to a New York Times report — — who was the first Republican-appointed appellate court judge to uphold the law. He also wrote a thorough, 26-page opinion outlining a conservative argument that the mandate is constitutionally sound.

Not surprisingly, the federal government quotes that opinion a lot in its court briefs.

Sutton hinted that he didn’t like the mandate but said Supreme Court precedent favors a growing expansion of Commerce Clause power and that Congress has latitude to address national problems.

““Call this mandate what you will —– an affront to individual autonomy or an imperative of national health care –— it meets the requirement of regulating activities that substantially affect interstate commerce,”” he wrote.

Scalia’s former clerk also argued that not buying insurance isn’t the same as sitting in a cabin in the woods, asking to be left alone –— a key piece of the federal government’s argument. Sutton wrote that such uninsured people are choosing to be “”self-insured,”” an ““activity”” that can be regulated by the government.

But the law’s opponents caution against reading too much into the Raich case, arguing that marijuana makes the case atypical. Plus, Scalia has a much longer record of traditional conservatism.

In a 1996 opinion in Printz v. United States, Scalia pointed out that when determining what Congress can and cannot do, the court looks to examples from the earliest days of Congress. He suggested that if a Congress hasn’’t ordered something before –— in that case, it instructed state officials to do background checks —– there’s reason to think the power never existed.

If “”earlier Congresses avoided use of this highly attractive power, we would have reason to believe that the power was thought not to exist,”” Scalia wrote.

The law’’s opponents say Scalia may look at the potential power to instruct consumers to buy a private product in the same way.

And even in his Raich opinion, Scalia suggested that there are still limits to what Congress can do.

““Although Congress’’s authority to regulate intrastate activity that substantially affects interstate commerce is broad, it does not permit the Court to ‘pile ‘inference upon inference'”’” to make it valid, he wrote.

Chief Justice John Roberts

Former acting Solicitor General Walter Dellinger, a strong supporter of the law, told a House committee last year that he’’d put money on Chief Justice John Roberts upholding the individual mandate.

And in doing so, he laid out a road map for the arguments Roberts could make — just in case Roberts is listening.

““I would wager that Chief Justice Roberts writes the opinion upholding the law,”” Dellinger said, adding that he thinks Roberts would want to write it himself to ensure it’s a narrow ruling. “”They’’re going to uphold it by saying in this case it is imminently intertwined with a fundamental part of the interstate markets in health insurance and health care.””

The key case that the health law’’s supporters point to as indicative of Roberts’’s thinking on the Commerce Clause is United States v. Comstock. In that case, Roberts joined the court’s liberal justices to write that Congress can enact a law that is linked —– or in legal terms, “”necessary and proper”” —– to a power explicitly written in the Constitution.

“”The same reasoning is here: The justification for the minimum coverage provision is that it is necessary to preserve the federal government’s ability to regulate insurance companies dropping people for pre-existing conditions,”” said Michael C. Dorf, a Cornell University Law School professor and former law clerk for Kennedy. Dorf called the opinion “potentially strong for the government.”

Roberts, as chief justice, is also perhaps most attuned to the court’s long-term legacy, several legal experts say.

““The chief justice has the greatest concern on the court’s position and standing,”” said Frank B. Cross, a law professor at the University of Texas at Austin. “”By nature, I think he’’s reluctant to have the court do something too radical.””

But the “radical” decision may be in the eye of the beholder.

Those who believe the mandate is unconstitutional argue that the Comstock opinion was written with several requirements a law must meet to make it constitutional, suggesting that Roberts sees limits on the Commerce Clause’s power.

Justice Anthony Kennedy

Kennedy has been the court’s swing vote since Justice Sandra Day O’Connor retired from the Supreme Court, and his opinion in the health reform case is being watched even more closely than in others.

Kennedy has made clear in several situations that anything the government wants to regulate has to have a strong tie to commercial interests in the Commerce Clause.

In a 1995 case, United States v. Lopez, Kennedy suggested in a concurring opinion that Congress can enact laws that try to address problems in the national economy.

“”Congress can regulate in the commercial sphere on the assumption that we have a single market and a unified purpose to build a stable national economy,”” he wrote.

And the federal government argued in its first Supreme Court brief defending the law that it’’s the same situation in health care. Government lawyers argued that the mandate is needed in order to regulate the health market –— one-sixth of the American economy –— and make the whole law work.

““What the federal government does [in the health reform case] is say this is a core federal regulation of the economy. It’’s needed,”” Dorf said. ““Maybe that’s an effort to get at Justice Kennedy for what he says in Lopez — — not to strike core functions of the federal government.””

Elizabeth Wydra, chief counsel at the Constitutional Accountability Center who believes the mandate is constitutional, said Kennedy is unlikely to believe the argument made by the 26 states: that if Congress can require Americans to purchase health insurance, it can require them to purchase anything.

““If he applies precedent, he’’ll feel comfortable that both the minimum coverage provision is constitutional under the Commerce Clause power based on precedent like Raich and not fall into the trap that many opponents of the act have set: that if you uphold the minimum coverage provision, there will be no limits on the Commerce Clause power,”” Wydra said.

But in the same opinion, Kennedy says that just because something is purchased doesn’t mean Congress can regulate it.

“In a sense, any conduct in this interdependent world of ours has an ultimate commercial origin or consequence, but we have not yet said the commerce power may reach so far,” he wrote.