"Anyone who says the individual mandate isn't in any trouble is just deluding themselves," Goldstein said. "It's not clear that it will be struck down but you cannot say from those arguments, that it's anything other than a toss-up. The (Obama) administration had as hard a time from those justices as they could have expected, and they are desperately hoping that they can pull together a fifth vote in favor of the mandate."
The justices never discuss internal strategy, and the full story of how health care was decided in the marble halls of the court may never be fully known.
The current waiting game has prompted anxiety and a touch of political rancor outside the court.
Legal sources say the White House has quietly set up an informal "war room" of sorts, ready to respond when the rulings are handed down.
Low-key coordination is under way between the White House Counsel's office, Political Office, senior Oval Office and campaign staff, Capitol Hill Democrats, as well as select outside advisers and friendly advocacy groups.
Republicans are quietly doing the same, with outreach to conservative activists and candidates. Managing the message will be all-important in a presidential election year.
Publicly, Obama has said he was "confident that the Supreme Court will not take what would be an unprecedented, extraordinary step of overturning a law that was passed by a strong majority of a democratically elected Congress, and I just remind conservative commentators that for years, what we've heard is, the biggest problem on the bench was judicial activism or a lack of judicial restraint, that an unelected group of people would somehow overturn a duly constituted and passed law."
Some conservative critics interpreted those remarks as a challenge to judicial authority, suggesting Obama was putting direct political pressure on the high court. Patrick Leahy, D-Vt., chairman of the Senate Judiciary Committee, urged the bench -- and Chief Justice John Roberts in particular -- to "do the right thing" and uphold the mandate.
Presumptive Republican presidential candidate Mitt Romney used the same words when urging a different outcome.
"I hope they do the right thing and turn this thing down," Romney told donors last week in Atlanta. "And say it's unconstitutional, because it is."
No one doubts the health care cases will have an immediate impact on Obama's re-election chances, as well as the long-term credibility of the federal courts, which are supposed to be beyond politics.
Recent polling suggests a "legitimacy crisis" in the Third Branch. A New York Times/CBS poll this month shows only 44 percent of Americans approve of the Supreme Court's job performance -- a steady drop over recent years. Three-quarters of those polled now say the justices are sometimes influenced by their political views.
A separate CNN/ORC International poll released June 8 found a majority -- 51 percent -- oppose the health care law in general, most because they think it is "too liberal," while 13 percent think it is "not liberal enough;" 43 percent of those surveyed favor the law.
The key players could be two conservatives on the court: Roberts and Justice Anthony Kennedy, long labeled a "swing" vote.
"With the four more liberal justices almost certain to vote to uphold the individual mandate, the administration is really hoping for the votes of either the chief justice, who signaled that he had questions for both sides," said Goldstein, "or the traditional swing vote in the court, Anthony Kennedy, who really was tough on the government lawyer but toward the end suggested that maybe insurance was special enough that he could vote to uphold the mandate."
Roberts has long talked about achieving consensus on divided issues, saying it brings long-term credibility and public confidence to the court's work. It has been mostly a pipe dream, as his nearly seven years of leadership has shown a continuing 5-4 conservative-liberal split on most hot-button issues.
"The court is bitterly divided over the individual mandate," Goldstein noted, "so if the administration is going to get his vote, it's either because he believes in a broad federal power or that he doesn't believe that the Supreme Court shouldn't overturn such an incredibly important economic statute."
Health care will soon enter the history books, among the handful of the high court's greatest cases, the outcome no doubt monumental -- legally, politically, socially. An issue that affects every American will naturally attract that kind of attention.
Picking winners and losers at this stage is a subjective, even partisan, exercise. The court itself will be both cheered and vilified however it rules. But as an institution, it has survived similar crises of confidence over its discretionary authority: slavery, racial integration, corporate power, abortion -- even Bush v. Gore.
Rapid-fire reaction to health care will be swift and furious, from the campaign trail, professional punditry, and halls of government. Some individual Americans stand to gain from the decision, others could be hurt -- financially, emotionally, and physically.
So why entrust all this in the hands of nine judges?
The Supreme Court usually gets the last word in these matters, regardless of whether one agrees with their decisions -- even matters of life and death, which many argue are the stakes in this health care debate.
Justice Robert Jackson may have put it best: "We are not final because we are infallible, but we are infallible only because we are final."