Owing to a congenital birth defect, Herkless was left unable to walk and was thus initially educated by private tutors. He entered the University of Glasgow and took an Arts degree and after graduating, spent some time traveling in Scotland before returning to school to study law. In 1883, he married Margaret Knox and she became a great help in his endeavors. Herkless became a fervent reformer and was appointed secretary of the University Council Reform Association in 1884. He eventually took the Chair of Scots Law at St. Mungo's College where he gained a reputation as an eminent lecturer. Although he produced various articles during his career, his main contribution to the law library was his collected lectures entitled Jurisprudence: or The Principles of Political Right, published posthumously in 1901. In 1911, his widow founded the Herkless Prize in his memory.
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Jurisprudence: or The Principles of the Philosophy of Right
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