Oliver Wendell Holmes’ dissent in the 1919 Abrams v. United States case is one of the most well known Supreme Court events in American history. It opened up a modern interpretation of the First Amendment, establishing freedom of speech as a civil value; it introduced the phrase “free trade in ideas” and the concept of “clear and present danger” into the American vernacular. The case has interested legal scholars for many reasons. One prominent one is the mystery of why Holmes, who had scorned the idea of constitutional rights for his entire career up to the 1919 case, suddenly adopted a tolerant view on free speech.

Thomas Healy, the author of The Great Dissent: How Oliver Wendell Holmes Changed His Mind—and Changed the History of Free Speech in America, saw something different in the case. While teaching a class on the First Amendment at Seton Hall, Healy began pondering the dissent as the end to a story rather than an ossified episode in legal history, putting to use his training as a journalist in addition to his knowledge as a lawyer and academic. He eventually began to suspect that there might be a conspiracy behind it.

“I knew that generally there were people around Holmes trying to get him to rethink his views on free speech,” Healy says. The people he’s referring to are what you might call Holmes’ groupies—young, progressive academics and judges who sensed the inner liberal in the aging, staid judge. They included Learned Hand, the oft-quoted New York judge, and Harold Laski, the British political theorist and academic whom, according to Healy, the childless Holmes treated like a son. But it wasn’t until Healy made a day-by-day timeline for the two-year period leading up to the landmark 1919 case that he felt sure Holmes’ Abrams dissent was, at least in large part, an effect of aggressive campaigning by his friends. “I tried to fill in every day and figure out everything that was going on in his life based upon letters, based upon what was in the news, based upon what the court was doing,” he explains. “And I have this timeline on my computer, and I kept looking at it, and looking at it, and when I saw the order of events, the scope of this campaign to change Holmes’ mind became clear to me.”

 As conspiracies go, this one to change Holmes’ mind is almost frustratingly gentlemanly. It happens mostly though eloquent letters and intimate conversations; arguments for tolerance and free speech are couched in deferential terms or even, ever so subtly, made through summer reading recommendations. (You almost have to pity Holmes when in one summer Laski has him reading two tomes of history—of English rationalism in the 19th century, and English democratic ideas in the 17th century—while the Supreme Court Justice Louis Brandeis suggests Holmes read a series of reports on the textile industry.)

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Healy comments that he has trouble finding the exact word for what Holmes’ friends were doing but that if their efforts were a conspiracy, it would be what in criminal law is called a hub and spoke conspiracy, with one person at the center—Laski. “He’s got the intent to change Holmes’ mind—and he’s communicating with these various people who may or may not be communicating with each other.” Yet it could also just be called an organized debate involving a “free trade in ideas”—exactly what Holmes dissent would allow other Americans to participate in today.Healy Cover

The Great Dissent confronts one big challenge of the critical biography—how to integrate big (and in Holmes’ case philosophical) ideas into a portrayal of the subject’s personal life—with impressive economy. “I don’t start off with a biography of Holmes,” explains Healy, who says that he generally doesn’t read biographies. “I tried to provide information about his life as you need it and interweave it with the bigger story.” As models for his book, Healy looked to Louis Menand’s book The Metaphysical Club (for the way Menand “makes ideas come alive”) and David Remnick’s King of the World: Muhammad Ali and the Rise of an American Hero (for how “Remnick used this pivotal moment in Ali’s life to tell us who Ali really was”). Healy’s lean storytelling results in a book that elucidates a complex historical event—in around 250 pages.

The Great Dissent is punchier than you might expect a book on a bygone Supreme Court justice to be, and pleasurable to read. But its relevance to free speech challenges we face as a country today should be what really wins it an audience beyond Holmes scholars and legal academics. “The debate we’re having about the balance between national security and civil liberties is the same debate that the country was having in 1918 and 1919 when Holmes changed his mind about free speech,” he explains, pointing to the cases of Edward Snowden and Bradley Manning, who was sentenced yesterday to 35 years in prison for leaking military secrets, as examples.

Though in the book Healy doesn’t make explicit the connection between the prosecutions of World War I protesters leading up to the 1919 Abrams dissent and our contemporary trials involving free speech, he believes that Holmes’ story contains important lessons. One of the most venerated American jurists of his time, a Civil War hero and a patriot, Holmes nonetheless spent most of his life not caring about civil liberties. But, as Healy points out, “through reflection, and through debate and discussion and reading, he comes to a realization that in the long run, we’re better off with more information, more speech.”

Alexia Nader is a freelance writer and an associate editor at The Brooklyn Quarterly. Her work has also appeared on the websites of The Oxford American and The New Yorker, and in the Los Angeles Review of Books.