Educated at Harvard, Holmes was commissioned a Lieutenant in the 20th Massachusetts Infantry in June 1861. He was wounded three times in three famous battles of the Civil War: Ball's Bluff, Antietam, and Fredericksburg, and was discharged with the rank of Lieutenant Colonel.
On leaving the Army, Holmes graduated from Harvard Law School, and in 1870, he became the editor of the American Law Journal. The following year, Harvard appointed him university lecturer on jurisprudence, and in 1882, he was awarded a professorship in the Harvard Law School. For 20 years, Holmes served on the Supreme Judicial Court of Massachusetts, and was Chief Justice the last three.
In 1902, President Theodore Roosevelt appointed Holmes an Associate Justice of the United States Supreme Court. Roosevelt had hoped to put Holmes' rather "liberal" mind to work for his administration. He was proven wrong in this as Holmes demonstrated his independence of mind in many dissenting minority opinions. This led to his title as "The Great Dissenter."
Until his retirement in 1932, he continued to demonstrate his originality of thought, his legal scholarship, and his mastery of pungent style. He died in 1935.