In the United States Supreme Court, he was dubbed “The Great Dissenter”

One of the interesting facts about Oliver Wendell Holmes Jr. is that it was on the US Supreme Court that he was named "The Great Dissident" Less than a year after starting as a professor at Harvard Law School, Holmes was appointed as an associate member of the Massachusetts Supreme Court of Justice. He served as Chief Justice of the Supreme Court for a brief period of time in 1899. In 1902, he received a nomination for the US Supreme Court from President Theodore Roosevelt.

Holmes has a reputation for offering incisive, succinct, and widely quoted insights. He presided over cases that covered the whole spectrum of federal law throughout his more than twenty-nine years on the Supreme Court's bench. He is renowned for his out-of-date views on a variety of subjects, including copyright, the law of contempt, the antitrust status of professional baseball, and the requirement that all citizens take the oath of allegiance. Like most of his contemporaries, Holmes believed that the Bill of Rights was a collection of prerogatives that British and American common law had accrued over the years.

Holmes was able to support this belief in numerous Court rulings. He is regarded as one of the finest judges in American history and represents numerous common law traditions that are now under attack by primitives who maintain that the Constitution's language is superior to any common-law precedent aside from the original reading of its meaning. He was known as the "Great Dissident" on the US Supreme Court because he frequently dissented from his colleagues. From January 12, 1932, until almost 30 years later, Holmes was on trial.