In the 1918 case of Sugarman v. United States, the Supreme Court ruled on a matter involving citizenship and military service. The petitioner, Sugarman, was born in Russia but had lived in America since he was two years old. He claimed to be an American citizen by virtue of his father's naturalization during his minority and sought discharge from draft as an alien enemy after being drafted into World War I due to his Russian birthplace (Russia having signed a separate peace treaty with Germany). The court held that although Sugarman could have acquired citizenship through his father’s naturalization while he was still a minor if certain conditions were met, it did not automatically happen upon reaching majority age without any action taken on part of the person involved. Therefore, because there wasn't sufficient evidence showing that these conditions were fulfilled before reaching majority age or that he took necessary steps for naturalization afterwards himself; henceforth it concluded that Sugarman remained an alien and upheld lower courts' decision denying him discharge from military service.

In the dissenting opinion for Sugarman v. United States, Justice Holmes argued that the majority's decision was based on a misinterpretation of the Espionage Act of 1917. He contended that Congress intended to punish not only those who directly obstructed military recruitment but also those who indirectly did so by creating an environment hostile to enlistment. In his view, Mr. Sugarman's distribution of anti-draft literature fell into this latter category and thus constituted a violation of the law as it stood at that time. Furthermore, he disagreed with the majority's assertion that such indirect obstruction was protected under free speech rights granted by First Amendment because he believed national security concerns outweighed these rights in times of war.