James Tolliver Bobbitt was the first son and third child of Tilman and Jane (Hill) Bobbitt. He was born in Monroe County, now West Virginia on March 10, 1836. The family lived ' on a farm near the village of Gates. Nearby lived numerous relatives who were mostly descendants of John and Permelia Bobbitt, and Sergeant James and Ann Hill. The family had moved from Rockbridge County, Virginia to Monroe County in 1827.
About 1843, Tilman and Jane Bobbitt moved from Monroe County to Greenbrier County and owned a farm near the village of Williamsburg. Several other members of the family soon followed and lived in the same area, most significant was the family of Oregon Bobbitt, a brother of Tilman Bobbitt. There was, however, much traveling back and forth between the families who had established in Monroe County and the families of Greenbrier County.
In 1854 Jane (Hill) Bobbitt, mother of James Tolliver, died. In the same year, on March 17, 1854, Emily Bobbitt was born, the last child of Tilman and Jane Bobbitt, and a sister of James Tolliver. On June 7, 1854, the first child, and sister of James, died. She was Susan (Bobbitt) Knight. John Bobbitt the grandfather of James Tolliver died in 1854 in Greenbrier County. Several relatives in the Hill family also died in the same year. For the 18-year-old James Tolliver Bobbitt it must have seemed like life was short and precarious.
On December 31, 1857 James Tolliver Bobbitt married Malinda Catherine Alderson in Monroe County. Malinda was a daughter of Albert Gallatin Alderson. Albert Alderson was a grandson of John W. Alderson, the first Baptist minister of Monroe County. The father of John W. Alderson was John Alderson Senior who was a native of Yorkshire, England. John Alderson Senior died in 1781, the same year that his son founded the Greenbrier Baptist Church. The Alderson family owned vast plots of land throughout the area. They were active in politics, religion, and commerce in the area. They built the Alderson Hotel and were instrumental in getting the Chesapeake and Ohio Railroad lines in the locality. In October of 1880 the town of Alderson, West Virginia was incorporated and named after this family. The stoic, wealthy Alderson family was not certain that their daughter, Malinda, had married into a family of progressive promise.
James Tolliver Bobbitt did not seek or receive any monetary favors from the Alderson family. Shortly after his marriage he went to work as an overseer on the plantation of his uncle, Rufus Bobbitt in Nicholas County. James and Malinda lived in the home with the Rufus Bobbitt family and in their home was born Joseph Alderson Bobbitt, their first child.