James Sterling Bobbitt was born on December 31, 1896 in Nicholas County, West Virginia. He was the last child of Elijah and Rowena (Robinson) Bobbitt. He was born on a farm on Muddlety which adjoined the farm of his maternal grandparents, James and Virginia Robinson. He along with numerous cousins of the community attended the rural schools of the county.
James Sterling Bobbitt was called "Sterling" all his life. He would not have known someone was speaking to him if they had called him "Jim". His father, Elijah Bobbitt, was a stern taskmaster and demanded hard work from all of his children. Sterling Bobbitt liked farm chores and learned from his father and surrounding farmers all the old methods of earning a living from farming.
In 1918, James Sterling Bobbitt was called to serve his country in France in the terrible World War 1. He was not yet 22 years of age, but along with several relatives and friends left the peaceful valleys of Nicholas County for what was pure hell in the trenches of France. He spent 48 days on the western front with the 313th Field Artillery on the West-Meuse River Valley in the Verdun area. Sterling Bobbitt was quickly promoted from private to corporal. He drove a team of horses in dense battles and saw horrors of death and destruction that no man would want to see again.
After the war, Sterling Bobbitt returned to Nicholas County where he helped his father on the farm. He took advantage of every opportunity to get more education. In 1923 he received his B.S. degree from West Virginia University. Following the war Sterling Bobbitt dated the beautiful Carolee Hill, daughter of Arch Hill on Muddlety. The couple were well matched and gossip all but had them married. The marriage never took place, mostly because in 1924 Sterling Bobbitt was offered a teaching assignment in Spanishburg, Mercer County, West Virginia.
On November 11, 1952, one of the Bluefield newspapers published a profile of Sterling Bobbitt, part of which read, "J. S. Bobbitt drove his Model T Ford to Mercer County from his native Nicholas County for a new teaching assignment at Spanishburg. He found several detours obstructing his journey over the state's poor mountain roads, and was forced to stop a number of times by auto trouble. In 1924, too, students were transported to school by trucks and four-horse wagons. Wagons were better able to negotiate the rut-filled, mud-filled roads. There were not many pupils then, but today J. S. Bobbitt, as assistant superintendent in charge of Mercer County's secondary schools, lists a total of 6,755 boys and girls transported on modern buses and over far superior routes.