The real determination of whether Roberts was crafty or sold us out will never be made if we succeed in taking the White House and both houses of Congress and the folks in Congress have the stones to pass a full repeal by using reconciliation to get it though the Senate (or mirable dictu we get 60 Senate seats), so in way, I hope we never find out.
But, while Obamacare is law, there are is still a manifestly unconstitutional provision lurking in it, but one not addressed in the suits the SCOTUS ruled on a week ago: the IPAB provision which attempts to bind future Congresses, and thus is prima facia unconstitutional. The same provision could also be challenged on the basis of the precedent in (of all things) Roe v. Wade, where the “reasoning” had nothing to do with abortion per se, but with government intrusion into the “private” patient-physician relationship. The IPAB is nothing but one huge intrusion of government into the “private” patient-physician relationship.
If a suit on either basis reaches the SCOTUS and Roberts leads a majority to invalidate Obamacare, notes it contains no severability clause and tosses the whole thing into the ashbin of history, he would indeed have out-foxed the left by establishing a precedent that limits Federal coercion of the states and the expansion of the Commerce Clause.
There’s a basic flaw within your very appealing theory: if Roberts decision was made to allow the other Constitutional arguments against ObamaCare to advance ( this allowing further precedents on the CC to be locked in) then he’s going to do even MORE damage to the Court’s precious reputation.
Speculation is that Roberts decided as he did to avoid the perception that the Court has become partisan. In this he failed, just that Conservatives now see it as partisan, with Roberts having flipped to the Liberal/Dem side.
Imagine the reaction from the Left if, next term, their newfound hero votes with a majority to overturn Obamacare on different grounds ... The story will be that a weak Chief Justice caved to Conservative outcry. THAT only does more damage to the destruction alreade wrought.