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Kentucky Genealogy and Biography, Volume 8B – Battle – Perrin – Kniffin, 1886.
WINSTON MAYO CONNOLLY, a native of Johnson County, Ky., was born January 30, 1842, and is a son of Constantine and Celia (Fairfield) Connolly, natives of North Carolina and Virginia respectively. The paternal grandfather of W. M. Connolly came to Kentucky in 1811, and first located on Boone Fork in Letcher County, but three years later removed to Johnson County. Constantine Connolly was born in 1805, was a farmer, a justice of the peace under the old Constitution, and was one of the three justices who composed the county court. He is still living in Johnson County. The Connollys are of Irish and the Fairfields of English origin, and the first settlement of the former family in America was at the present site of Charleston, S. C., which was then known as the Connolly Reservation. Of the nine children born to Constantine and Celia Connolly all are living with the exception of Henry J., who was a graduate of Miami Medical College, Ohio, a practitioner of Boyd County, Ky., and who died in 1880. Winston Mayo Connolly passed his early life on the farm, his educational advantages being those of the common schools only, though he received a knowledge of trigonometry, navigation and surveying. He subsequently clerked a while for his brother, Harmon Connolly, who was Quartermaster of the Forty-fifth Kentucky Cavalry, United States army. In the fall of 1865 he read law with John M. Burns, was admitted to practice in Johnson County, June 19, 1866, where he remained two years, then removed to Kansas, and in connection with the practice of his profession taught school. However, in 1870, he returned to Pike County, Ky., where he has since been actively and successfully engaged in practice of the legal profession. June 20, 1887, he formed a partnership under the firm name of Auxier, Ferrell, Connolly & McGinnis. In 1874 Mr. Connolly was elected county attorney and served one term. September 13, 1871, he married Miss Mary J. Ratliff - a daughter of Harrison and Margaret (Hatcher) Ratliff - a native of Virginia. They are the parents of two children, viz: William Henry Harrison and Nona Bertha. Mr. Connolly is a member of the Masonic fraternity, owns six or seven thousand acres of land, is a Democrat politically, and affiliates with the Presbyterian Church.