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A piece of jurisprudential sleuthing, this article uncovers the back story for a puzzle unanswered by legal historians for some eighty years: Why would the free-speech libertarian Louis Brandeis write the most famous paean to First Amendment normative values in his opinion in Whitney v. United States, and yet join (by way of a concurring opinion) the judgment of the majority of the Court that would have sent the "patrician radical" Anita Whitney to prison for a 14-year term solely for participating in the formation of the California Communist Labor Party? Part of the puzzle is provided by the unpublished Brandeis opinion in Rutherford v. Michigan, which is provided as an appendix to the article. This work was publicly recognized for its excellence in the Legal History Blog.