In the 1918 case Matters v. Ryan, the United States Supreme Court dealt with a dispute over mining claims in Alaska. The plaintiff, Matters, alleged that he had been defrauded by Ryan and others who had conspired to obtain his mining properties through fraudulent means. He sought an injunction to prevent them from working on these mines and selling the minerals they extracted. However, both lower courts dismissed his suit due to lack of equity jurisdiction because there was an adequate remedy at law - namely damages for fraud or trespassing. The Supreme Court affirmed this decision stating that if a legal right is disputed and it can be settled by common-law action (like damages), then equity has no jurisdiction unless some special ground for equitable relief is shown such as irreparable injury or inadequacy of legal remedy which were not demonstrated in this case.

In the dissenting opinion for Matters v. Ryan, Justice Holmes disagreed with the majority's decision to uphold a law that made it illegal to distribute literature encouraging resistance to World War I draft laws. He argued that such a restriction on free speech was unconstitutional unless there was clear and present danger of immediate harm resulting from the speech in question. In this case, he did not believe that distributing anti-draft pamphlets posed an imminent threat to national security or public safety. Therefore, he believed it should be protected under the First Amendment right to freedom of speech. His view reflected his broader philosophy about free expression: society benefits when all ideas are allowed into marketplace of ideas where they can compete freely without government interference.