In the middle of September Cheshire left Monreath to take up his duties at St. Clement's Hall. Before he left home his father gave him fifty dollars to aid him until he should receive a part of his salary. This was the last time he ever gave him any money, that is, from a feeling of responsibility for his son's support. At St. Clement's Cheshire was given all the upper classes in Latin and Greek, and in addition taught some arithmetic and algebra. In consequence of his rather poor beginning in Latin and Greek at the Tarboro Academy, he never became a scholar in these fields. While teaching Latin he became more interested in this subject and read rather widely in Tacitus and other Latin authors. In the course of his busy life of teaching he found time to continue "a kind of study" of Blackstone which he had begun in his senior year at Trinity. He also read through Kent's _Commentaries_ and a good deal of English poetry. Cheshire came to know a number of people in the neighborhood of the school who helped to make his life at St. Clement's more interesting and pleasant. He spent a good many week-ends in Baltimore with some of his Trinity friends. When his oldest and best friend, Richard Lewis, came to Baltimore to study medicine in the fall of 1870, his visits became more frequent. On the whole, his life at St. Clement's was happy, and the experience he gained, worth while. He never, however, became fond of teaching, but he enjoyed his students and took a warm personal interest in them. After two years at St. Clement's he decided to abandon teaching for the law profession, which he thought would be more congenial to his tastes. When Cheshire returned to North Carolina in June, 1871, he went with his family to Hillsboro to spend the summer. Here he began the study of law under the eminent lawyer, William K. Ruffin, son of Chief Justice Thomas Ruffin, who coached law students since he was too crippled to do much active practice. Ruffin was a "devotee" of the common law and always gave his students a thorough drilling in it. He made Cheshire devote almost all the summer to the study of Second Blackstone and Cruise's _Real Property_. When he left Hillsboro in September, Ruffin made him promise that he would secure an old folio edition of Coke's _Commentaries on Littleton_ and read it carefully. Some time later Cheshire bought a copy of this work in Baltimore and read it from cover to cover as he had promised. He once remarked that he believed he was the last man in North Carolina to have completely read the old folio edition. Cheshire found Mr. William Ruffin "a most interesting man as well as a stimulating and helpful teacher."[4]