There is probably no figure in American jurisprudence who has been more studied and whose record has been more analyzed than Oliver Wendell Holmes, Jr. Among the aspects of Holmes' career that have commonly piqued the interest of scholars is the apparent transformation of Holmes' views of the First Amendment and freedom of expression rights. In 1919, Holmes began a redirection of the United States Supreme Court in its interpretation of these rights with a dissenting opinion in which he set forth a broader approach than what had previously been used-and what Holmes himself had previously held. Why the transformation in Holmes? It is posited in this article that the philosophy that had been simmering in Holmes rose to the surface in 1919. It is a philosophy of individualism and non-conformity. In short, it is Ralph Waldo Emerson's philosophy of self-reliance.