Jonathan Adler asks the question: why did legal elites underestimate the case against the mandate?
You might want to give quick and flippant answers—such as, for instance, “because they’re stupid and biased”—but that really doesn’t tell us much. Legal elites may be biased (as is just about everyone), but they’re most definitely not stupid, at least not in the academic sense.
The answers Adler gives are much more interesting. His first point is that legal academics are often too far removed from the realities of actual practice; the ivory tower effect and all that. His second is that legal academics tend to on the left, which creates an unavoidable echo chamber effect that limits them. Related to this is the following, which I think is a brilliant insight:
As I’ve heard Paul Clement (among others) explain, you can’t effectively advocate your own position until you truly understand the other side. This can be difficult to do, particularly when we have strong feelings about a subject.
This not only applies to law but is equally true for almost everything, including how we conduct ourselves in our personal affairs.
Since my “change” experience, I’ve been more and more convinced that many liberals do not try to understand conservatives, or to pay attention to the actual substance and weight of their arguments. Rather, they tend to dismiss them out of hand as biased and/or self-centered and/or cruel, without understanding the reasoning behind them. And although conservatives like to think they’re above doing the same in return, I think many conservatives fail to understand where liberals are coming from. I like to think (rightly or wrongly) that I understand both a bit better than most, because I’ve looked at liberals and conservatives from both sides now.
The differences between the philosophical underpinnings of conservatism and liberalism are things I’ve explored before, many times, as have so many others. But right now it will suffice to say that those differences have to do with big questions like the nature (bad? good? neutral?) and perfectibility of humankind, how best to achieve goals (through government or individual action), and the importance of liberty and what is the price we are willing to pay for it.