Jonathan’s post is a must read.  Here is an excerpt:

Premier appellate litigators may have a good sense of how the Court is likely to assess complex constitutional law claims, but elite legal academics, not so much.

What explains this state of affairs?  I believe there are several factors at work, but one in particular is the increasing separation of the legal academy from the practice of law — a separation that is greatest in fields, such as constitutional law, that touch on broad questions of public policy.  At many schools, academics are more interested in developing a comprehensive theory of justice than in divining the nuances buried in the Court’s cases.  Junior academics are routinely discouraged from doctrinal scholarship and pushed to develop broad overarching and original theories for what the law should be.  Constitutional scholarship in particular is increasingly focused on theory and less on the law.  In some corners, it’s more important to reconcile one’s claims with the writings of John Rawls than the opinions of John Roberts.

Another factor that contributes to this problem is the relative lack of ideological diversity within legal academia.  The current Supreme Court has a right-leaning majority, but legal academia leans decidedly to the left.  On many faculties their are few, if any, professors with any particular appreciation or understanding (let alone sympathy) for the jurisprudential views of a majority of the current justices.  This means that when ideas are floated in the faculty lounge, they may get a far more sympathetic hearing than they would ever receive in court.  So, for instance, it’s easy for Jack Balkin to dismiss an argument premised on Bailey v. Drexel Furniture because it’s a Lochner-era decision, even though Bailey remains good law.  A practicing lawyer would have been less likely to make this mistake.  Indeed, the SG actually cited Bailey approvingly this week in his argument before the Court.

I agree with Jonathan entirely.  It should be noted that this preference for broading overarching theories actually has influenced the right, as originalism as a constitutional approach is one such theory.  Still, originalists tend to recognize that the Court is not an originalist court in the main.  It appears that constitutional theorists on the left more  often forget that the justices’ views are not always to the theorist’s liking.