As promised, I have a prediction to make concerning the individual mandate of Obamacare. Before I make it, let me explain what I have done.
I assume, for the sake of argument, that Justice Anthony Kennedy will be the swing vote. That means a lineup of John Roberts, Samuel Alito, Clarence Thomas, and Antonin Scalia against the constitutionality of the mandate and a lineup of Stephen Breyer, Ruth Bader Ginsburg, Sonia Sotomayor, and Elena Kagan for the constitutionality of the mandate.
I have read (this morning) Justice Kennedy's opinions in three recent Commerce Clause cases: United States v. Lopez (1995), United States v. Morrison (2000), and Gonzales v. Raich (2005). Justice Kennedy wrote separately in the first of these cases but signed on to the majority opinion in the others. In Lopez and Morrison, Justice Kennedy voted to strike down legislation in cases involving noncommercial activity. In Raich, Justice Kennedy voted to uphold legislation in a case involving commercial activity. If the only salient distinction were commercial/noncommercial, then Justice Kennedy would probably vote to uphold the constitutionality of the mandate, since it's clearly commercial in nature.
But there's another distinction in play, namely, activity/inactivity. If Justice Kennedy finds this distinction salient, he may well vote to strike down the mandate. If he doesn't, he probably won't. In note 29 of Raich, the majority (which includes Justice Kennedy) wrote: "It has long been settled that Congress' power to regulate commerce includes the power to prohibit commerce in a particular commodity." The question at issue with regard to Obamacare is whether Congress's power to regulate commerce includes the power to mandate commerce in a particular commodity. To my knowledge, this is a novel constitutional question (which is why it is ludicrous for progressive law professors to proclaim this an easy case).
Justice Kennedy is known to give significant weight to individual liberty in his rulings. In Lawrence v. Texas (2003), for example, he voted to strike down state anti-sodomy statutes on the ground that they violate the right to liberty protected by the Due Process Clause of the 14th Amendment. As he put it, "It is a promise of the Constitution that there is a realm of personal liberty which the government may not enter." Lawrence did not involve the Commerce Clause, but both cases implicate individual liberty. I can see Justice Kennedy arguing that the federal government goes too far when it coerces individuals into purchasing a product—health insurance—that they don't want and don't need. If liberty means anything, it means not being forced to engage in commerce.
I predict that Justice Kennedy will find the activity/inactivity distinction salient. He will, accordingly, vote to strike down the individual mandate, on the ground that Congress lacks the power under the Commerce Clause to require commercial activity. I would not stake too much on this prediction; but if I had to wager, that's how I'd wager.
Addendum: I thought of a pithy way to make my point. In Morrison, Chief Justice William Rehnquist (writing for the majority, which includes Justice Kennedy) wrote: "Where economic activity substantially affects interstate commerce, legislation regulating that activity will be sustained" (quoting the majority opinion in Lopez; italics added). The reason legislation was struck down in Lopez and Morrison is that the regulations in question were not economic. The reason Obamacare may be struck down is that the regulation in question (the mandate) does not govern activity.