The Volokh Conspiracy
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Today in Supreme Court History: October 21, 1919
10/21/1919: Abrams v. United States argued.

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During World War I, Jacob Abrams and four other Russian immigrants living in New York City had printed and distributed two leaflets condemning U.S. intervention in the Russian civil war involving the Bolsheviks (communists). The leaflets did not concern the war with Germany. In the course of an appeal to the “workers of America,” one leaflet advocated a general strike and a resort to arms if the United States intervened in Russia.
https://firstamendment.mtsu.edu/article/abrams-v-united-states/
The majority argued that "the plain purpose of their propaganda was to excite, at the supreme crisis of the war, disaffection, sedition, riots, and, as they hoped, revolution, in this country for the purpose of embarrassing, and, if possible, defeating the military plans of the Government in Europe."
Justices Holmes replied with the first of his great free speech dissents. He argued that "Now nobody can suppose that the surreptitious publishing of a silly leaflet by an unknown man, without more, would present any immediate danger that its opinions would hinder the success of the government arms or have any appreciable tendency to do so."
The fact that these people were not American citizens did not stop him from finding a violation of the First Amendment.
Holmes ends modestly:
"I regret that I cannot put into more impressive words my belief that, in their conviction upon this indictment, the defendants were deprived of their rights under the Constitution of the United States."
The defendants were ultimately deported.
https://jwa.org/encyclopedia/article/steimer-mollie
The majority argued that "the plain purpose of their propaganda was to excite, at the supreme crisis of the war, disaffection, sedition, riots, and, as they hoped, revolution, in this country for the purpose of embarrassing, and, if possible, defeating the military plans of the Government in Europe."
And? This decision should be considered to be implicitly overruled by Brandenburg v. Ohio, 395 U.S. 444 (1969). Imagine President George W. Bush having Cindy Sheehan arrested based on Abrams.
Yes, like other moments in legal history that people provide brief discussions of, the opinion eventually no longer held up.
"The fact that these people were not American citizens did not stop him from finding a violation of the First Amendment."
GASP!
Um, this is TRUMP'S AMERICA now and we'll not have any talk like that.