James William Crain was born on December 15, 1828 in Hillsboro, Kentucky to parents William Crain and Rebecca Moffett Crain; he was the second of eight children for the couple. While working as a clerk in Shropshire's Store in Lexington, James met Celia Russell Hunt, another Fleming County native who had moved to the city after her mother's death. James and Celia married on December 12, 1854 in Fayette County at the home of her half-siblings and in 1858 they returned to Fleming County where James again worked as a clerk. It was in Fleming County where both their children, James Russell Crain and Sallie Rebecca Crain Garr, were born. Their life of the young family was disrupted in 1865 when Celia passed away from tuberculosis, leaving James a widower with two young children. 

James married a second time to Martha Jane "Jennie" Oliver. This marriage resulted in three children: Celia Louise Crain, William Kennan Crain, and Eugene Humphrey Crain. Though Jennie was Sallie's stepmother, Sallie seems to have been very fond of her, referring to her as her mother in her diary, and writing of her distress when she passed away. After his return to Fleming County in 1858, James remained in the county for the rest of his life, and was a prominent citizen. He not only continued his work as a merchant, but was also a police judge and represented the county in the State Legislature. He was remebered as a legislator for introducing a bill for the prohibition of alcohol in Fleming County. It was in Fleming County where he passed away at the age of 80 in 1908 from a kidney condition. He is buried in the Hillsboro Cemetery in Fleming County, Kentucky.

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