Modern free speech jurisprudence begins with the words and wisdom of Oliver Wendell Holmes Jr. Whatever one may make of that, it is impossible to deny. Whether Holmes was a liberal or a libertarian, a pragmatist or a nihilist, a defender of individual rights or of majority will, a social Darwinist or a totalitarian, or a “Jekyll-Holmes and Hyde-Holmes” as Albert Alschuler has branded him, is difficult to say absent nuanced elaboration. What is easier to gauge is his enormous impact on how we – laypeople and lawyers alike – think and talk about our system of freedom of expression. This is not necessarily because of the analytical soundness of his opinions but rather, to echo Judge Richard Posner, because of his “rhetorical skill.” That is, “Holmes was a great judge because he was a great literary artist.” His “specialty was great utterance,” said Felix Frankfurter. If “we care for our literary treasures,” added Frankfurter, “the expression of his views must become part of our national culture.”

The most memorable and important instances of judge-announced law cannot always be reduced, as Holmes well understood, to Kantian formulas thereafter stamped as precedents. They often consist of statements that awaken within us readily recognizable emotions or instantly persuasive ideas or even enticingly provocative thoughts. By that measure, Holmes's many statements on free speech remain touchstones in our free expression discourse. Then again, other lesser-known Holmes statements reveal a jaundiced view of our First Amendment freedoms.