Holmes was on the Massachusetts Supreme Judicial Court for 20 years, and wrote nearly 1,000 opinions there. As a justice and later chief justice of the Massachusetts Supreme Judicial Court, Holmes had extensive trial duties, both at law (with a jury) and in equity. He tried dozens of cases per year. About 4/5 of his rulings as a trial judge were upheld on appeal to the full court. 1/5 were overturned. At that time, the justices sat on the full court when their own trial-level rulings were reviewed. Holmes himself wrote a few of the decisions overturning his own trial-level judgments. O.W. Holmes: a Life in War, Law, & Ideas.
First Amendment
Much later in his career, Holmes upheld the convictions of the socialist presidential candidate Eugene Debs and other dissenters who spoke against World War I. But later, under the influence of Justices Brandeis and Frankfurter, he changed his mind on free speech, and dissented from decisions upholding the convictions of anarchists. (The Great Dissent: How O.W. Holmes Changed His Mind & Changed the History of Free Speech in America.)
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