I'm not sure if you'd consider Charles Krauhammer a legal expert, but I certainly consider him well qualified for comment:
Charles Krauthammer: Why Roberts did it - The Washington Post
It’s the judiciary’s Nixon-to-China: Chief Justice John Roberts joins the liberal wing of the Supreme Court and upholds the constitutionality of Obamacare. How? By pulling off one of the great constitutional finesses of all time. He managed to uphold the central conservative argument against Obamacare, while at the same time finding a narrow definitional dodge to uphold the law — and thus prevented the court from being seen as having overturned, presumably on political grounds, the signature legislation of this administration.
Why did he do it? Because he carries two identities. Jurisprudentially, he is a constitutional conservative. Institutionally, he is chief justice and sees himself as uniquely entrusted with the custodianship of the court’s legitimacy, reputation and stature.
My general impression of Mr. Krauthammer is positive. At times I've thought the things he said were spot on, but I recall at other times thinking they weren't correct or particularly helpful to the general understanding or something like that. It's been a while since I've heard him though, so I suppose I don't have much in the way of an opinion of him.
As for those specific comments: At first blush I don't agree with the last paragraph, but there certainly could be some truth in those sentiments. And some of my initial thoughts were similar to some of the thoughts Mr. Krauthammer expressed in the first paragraph.
Here's the thing about the Chief Justice (at least, one of the things I see having read some of his opinions and listened to him during oral arguments). He's not as much of a technician as many lawyers seem to be. He doesn't seem obsessed with formalism. He seems to care about substance, even if it isn't rigorously packaged as it might supposedly need to be. Following on our discussion from earlier, I might say that he presents as a bit simpler than other Justices do - simpler, more straightforward thoughts, simpler expression of those thoughts. I'm not suggesting he's not as intelligent, far from that. I guess I'd say that, particularly during oral arguments, he cuts to the chase better than others do.
He once concluded a single paragraph opinion with the quote:
"The Constitution deals with substance, not shadows." That quote had been taken from Justice Fields who, writing in 1867, used it to eschew the notion that form was more important than substance. In essence, he was asserting that if two things were functionally the same, if they had the same practical import, if they necessarily lead to the same consequence, they might ought to be treated the same - the reality that they'd been given different names or described with different words notwithstanding. Basically, if it walks like a duck and quacks like a duck, it's a duck no matter what you call it.
I suppose the point I'm getting at is that, in hindsight, this (taxing power) reasoning from Chief Justice Roberts isn't all that surprising - it isn't particularly out of character. There's little dispute that, under existing precedents, if the mandate is a tax it's constitutional. James Madison wouldn't necessarily agree that it is, but the Court's past rulings would seem to make it so. It's also fair to argue that the mandate - i.e. the penalty for failing to meet it, which is the only consequence to it - is a tax in all but name. There's a reason it wasn't generally touted as a tax by its supporters and I'd bet you already get that reason. It was political - taxes aren't generally popular or well received. In a righteous world, maybe we should make the supporters of the law (and the mandate in particular) sleep in the bed they made - they chose not to market it as a tax, so they don't get the benefit of it being considered as one. But I suppose the Chief Justice didn't feel he had the authority to impose that sleep-in-the-bed-you-made reality. He had to take the law as it was, however it came to be that way - and that meant considering a duck a duck even if it went by a different name. The Constitution deals with substance, after all, not shadows - not symbolism - not inconsequential form. Once he was to the point that he felt he had to give the mandate the benefit of the doubt as being a tax, he either had to uphold it or overturn many decades of precedent (and with them, major established government programs like Social Security that were dependent on those precedents).
So, here we are. That's generous speculation regarding how the Chief Justice got where he got. How true to reality is it? I don't know. Lots of speculation could be offered in this regard. Who knows how accurate any of it is? We can do little more than believe what we want to believe, or simply accept that we don't (and may never) know.
That stuff said, I've read some of the opinions now and I have about 6 million strands of thought - maybe more, I got tired of counting. For now, I'd just say that there's something hanky about these opinions. I can't put my finger on it but something doesn't feel right. I'm not talking about how complicated they are - and they are rather complicated. It's a bit of a chore to sort out what the real import of all of the different votes, and the different Justices' respective reasonings for those votes, is. This decision is unusual in a lot of ways, but ways that are at least articulable. I'm referring to something else though. Like I said, something that just doesn't feel right - something about the tone and construction of the opinions. They feel more cobbled together than they should. The propriety of the judgments and wisdom of the reasoning(s) aside, the work product - the actual writing of the opinions - just feels sub par to me. Boy I wish I could have been in the room when they were discussing this case.