Admittedly, I'd rather have the day that the anti-ObamaCare side had than the one its proponents did. All that being said, it's impossible to predict the outcome of any case by the questions the justices ask. What's more, despite the excerpts highlighting Anthony Kennedy's skepticism about the law, there were moments when he likewise seemed skeptical of the constitutional attacks on it. After Paul Clement -- the lawyer arguing on behalf of the 26 states resisting the imposition of ObamaCare -- argued that the uninsured were not market participants (and hence not engaged in "commerce," which is a justification that would allow the federal government to legislate), Justice Kennedy noted:
"But they [i.e., Americans who choose not to purchase health insurance] are in the market in the sense that they are creating a risk that the market must account for."
This remark indicates that, at least in Justice Kennedy's mind, there is at least some argument on the other side -- this isn't a slam dunk. Take Wickard v. Filburn, a Supreme Court case from 1942. The case occurred at a time when the federal government had limited the amount of wheat a farmer could produce, based on the acreage of his farm (a version of wheat price supports). In that case, the Court held that a farmer, growing excess wheat on his own farm for no other reason that his own consumption, could be fined and ordered to destroy the extra wheat.
In the majority's reasoning, Farmer Filburn's production of excess wheat for his own use on his own farm would reduce the amount he would have to buy on the open market. This would, in the Court's reasoning, distort the wheat market, which is traded nationally. Hence, the law could be upheld given the federal government's power to regulate interstate commerce.
Now, there are ways to distinguish Wickard from the present case -- most particularly because here, the federal government is attempting to create commerce (by forcing people to buy insurance) in order to regulate commerce. There, the commerce already existed. But the case shows that there is an argument to be made on the other side, and even thinking about taking a victory lap for the striking down of ObamaCare is hideously premature.
Justice Kennedy at least raised the possibility that, in his mind, health care may a be a unique case. If he would ultimately side with the four more liberal members of the Supreme Court (Justices, Ginsburg, Breyer, Sotomayor and Kagan) on the constitutionality of the individual mandate based on the Constitution's Commerce Clause, chances are that Chief Justice Roberts (who didn't heavily tip his hand yesterday) might also decide to join the majority.
The Chief Justice's reasoning would presumably be that because as Chief, he retains the prerogative to assign the writing of the opinion on the side he joins (the senior-most justice on the other side has the same privilege), he could perhaps write a more limited endorsement of the mandate's constitutionality. That's how, conceivably, ObamaCare could be narrowly upheld with a 6-3 majority.