R. R. PICKERING, sheriff, was born April 17, 1850, in Caldwell County, Ky., and is a son of Thomas W. and Minerva (Cook) Pickering, both natives of the same county and State. M. A. Pickering, subject's grandfather, was born in Tennessee, and in an early day came to Kentucky, settling in Caldwell County, where he died in 1870, aged eighty-two years. Mrs. Pickering's father, James Cook, was a North Carolinaian [sic] by birth, and came to Kentucky when Mrs. Pickering was a child, locating in Caldwell County, where he died in 1855. Thomas W. Pickering was for many years one of the leading farmers and active business men of Caldwell County, having filled several official positions at different times. He died January 25, 1882, at the age of sixty-six years. Subject's mother died in 1878, at the age of sixty-six years. Mr. and Mrs. Pickering were the parents of eleven children, six of whom are living: John M., Martha (wife of Samuel Lapradd), M. A., Thomas W., R. R. (subject), and Minnie (wife of P. R. Hunter). R. R. Pickering was reared a farmer, which business he followed until 1875, when he was appointed deputy sheriff under his father, and later with F. J. Harris, serving as deputy about four years and eight months; he was elected to the office in 1882, and re-elected August 4, 1884. He is one of the most careful and painstaking sheriffs the county has ever had, and his popularity is attested by the fact that he received the unanimous vote of the county at his second election. On the 26th of November, 1879, he was united in marriage with Miss Lizzie M., daughter of J. N. and Elizabeth (Harker) Wiley, of Caldwell County. Mr. and Mrs. Pickering have had two children, both deceased; their names were Carrie and Gracie. Mr. Pickering is an active member of the Masonic fraternity, and has been a life-long Democrat.
Source: J. H. Battle, W. H. Perrin, & G. C. Kniffin. Kentucky. A History of the State. Louisville, KY, Chicago, IL: Battey, 1885. Page 711.