He also began to rethink his stance on the First Amendment, an endeavor his young friends encouraged. For more than a year, they waged an intense behind-the-scenes campaign to strengthen Holmes’s appreciation for free speech. They fed him books on political liberalism, wrote him long letters on the value of tolerance and engaged him in impassioned debates. At one point, Laski even arranged a meeting at his summer bungalow between Holmes and Zechariah Chafee, a Harvard law professor who had written an article criticizing the justice’s views. “You won’t forget that you are coming down on Saturday for the week-end,” Laski wrote Chafee. “Holmes is coming to tea, and I want you to arrive in good time. For I have given him your article and we must fight on it.”

Holmes did not change his mind all at once. In March 1919, he wrote three opinions for the court upholding the convictions of socialists for criticizing the war. These opinions hinted at an internal struggle. Holmes retreated from his earlier belief that free speech protects only against prior restraints. And he rejected the “bad tendency” test, writing that speech can be punished only if it poses a “clear and present danger.” But he failed to explain how the defendants’ speech met that test, falling back instead on his commitment to majority rule and judicial restraint.

Eight months later, when the court heard another case under the Espionage and Sedition acts, Holmes’s conversion was complete. By this point, Laski was in serious trouble, having spoken out in support of a labor strike by Boston police officers. The strike was a disaster; with no officers on duty, the city descended into chaos, and the soldiers who were brought in to restore order killed eight people. Laski’s support for the strike thus won him the enmity of the entire New England establishment. The press denounced him as an “boudoir Bolshevist,” while the Harvard Board of Overseers opened an investigation to determine whether he was fit to teach.