Thanks, Jonah, for the plug. The review you have in mind concerned a book-length attack on Holmes. I didn’t like the book much–the author of the book wrote a sharply-worded letter, if I recall correctly–but also criticized Holmes’s theory of the law:

Admirers can, it is true, point to other Holmes remarks that suggest that he retained a romantic streak. But on examination, what he is romanticizing usually turns out to be war, will, and death.
To see how Holmes’s dark vision affected his legal thought, one need look no further than his seminal article, “The Path of the Law,” published in the Harvard Law Review in 1897. In this article he laid out his definition of the law, his “prediction theory”: “The prophecies of what the courts will do in fact, and nothing more pretentious, are what I mean by the law.” He also wrote, “If you want to know the law and nothing else, you must look at it as a bad man, who cares only for the material consequences which such knowledge enables him to predict.” The use in law of moral terminology–words such as “duty” and “right”– was an obstacle to “the clearness of our thought.” Holmes applied these points to the law of contracts: “The duty to keep a contract at common law means a prediction that you must pay damages if you do not keep it,–and nothing else.”
Holmes conceded that the law reflects the prevalent moral sentiments of the time it was made, but wanted to evacuate any moral content from the analysis of law. This view might be criticized for its amorality, and Alschuler does so. But he also argues that it fails as a matter of description. A prediction theory of the law makes unintelligible the notion that a court can get the law wrong. How, for example, can one use that theory to make sense of the dissents Holmes wrote on the Supreme Court? Indeed, the theory offers almost no guidance to any judge. You can’t decide a case by predicting how you will decide it. A theory of the law that cannot see the law from a judge’s point of view cannot truly describe the law.
Some of Holmes’s letters suggest that he also believed that the test of a good law was that it reflected “the dominant force” or “equilibrium of power” in a community. They suggest, as well, that this view was the foundation of Holmes’s judicial restraint. In 1914, he wrote to Felix Frankfurter: “I quite agree that a law should be called good if it reflects the will of the dominant forces of the community even if it will take us to hell.”
This view is vulnerable to some of the same objections as the prediction theory of the law. . . .

I went on to argue that Holmes “beg[a]n the process of detaching the argument for judicial restraint from objective morality,” and that this wrong turn is part of what has made our contemporary debates about judicial power so unsatisfying.