In the 1919 case of Cartas v. United States, the Supreme Court dealt with issues related to citizenship and naturalization laws. The petitioner, Mr. Cartas, was a Spanish subject born in Cuba who had moved to Florida before Spain ceded control of Cuba to the U.S following the Treaty of Paris in 1898. He argued that he automatically became a U.S citizen when this transfer occurred due to his residence in Florida at that time. However, according to existing law then (the Act of April 14th, 1802), only "free white persons" could be admitted as citizens through naturalization process which excluded him from automatic citizenship because he was not considered "white". The court ruled against Mr.Cartas stating that even though he resided within US territory during annexation period , it did not grant him automatic citizenship status . This decision reinforced racial restrictions on American Citizenship by upholding whiteness as an eligibility criterion for naturalization.

In the dissenting opinion for Cartas v. United States, Justice Oliver Wendell Holmes Jr. argued that the First Amendment should protect even speech advocating violence or illegal actions unless it posed a "clear and present danger." He believed that the majority's decision to uphold Cartas' conviction under the Espionage Act of 1917 was an overreach of government power and violated his right to free speech. Holmes contended that just because someone advocates for something does not mean they are inciting immediate lawless action, which he felt should be a requirement for such convictions. The justice also expressed concern about suppressing unpopular opinions, arguing this goes against democratic principles as it prevents society from being exposed to differing viewpoints which could potentially lead to societal progress.