According to Sadie Smathers Patton, William and Louella Bobo Montgomery had three children: John, William Jr., and Lily. Not much is known about Lily, except that, as Patton writes, she “died early.” The 1900 census lists a young girl named Lillie who may have been William and Louella's daughter. She was living with her uncle, Wiley Bennet, along with her aunt, Myrah Montgomery, and a possible cousin, Elmira Montgomery.

A few records have been found that shed light on a pivotal and likely transformative period in John Montgomery’s early adult life.

In his late twenties, John Montgomery was convicted of manslaughter. At the time, he was living in Pineville, located in Bell County, Kentucky. Pineville is about 200 miles from his childhood home in southern Henderson County, North Carolina, but the rural Appalachian town must have felt at least a little familiar, as it is surrounded by the same ancient and gently sloping mountain range that he grew up with back in western North Carolina.

Bell County was typical of rural central appalachia during the industrial revolution. Rich in natural resources, the development and population of the area was heavily shaped by the local lumber, coal, and railroad industries. It is not yet known if John Montgomery worked in any of these industries, or was employed in a field associated with the growing infrastructure and population of Bell County.

What is known is that in 1909, John was convicted of killing a man named Nelson Daugherty and was sentenced to two and a half years in the Kentucky State Penitentiary, 145 miles from Pineville. He had spent about three months in jail in Bell County before his transfer to the prison.

Prison records and the 1910 Federal Census reveal more about John during this time. In 1910 he was 28 years old. If this record is accurate, it means he was born in 1882, the same year that the Kingdom community had pooled enough money to buy property, and their mother, Louella and their uncle Robert signed the deed.

The 1910 census also shows that John had been married to his second wife for four years, and worked in the prison’s shoe shop. He could not read or write but was listed as a homeowner. By the time of his release on April 22, 1911, he had also worked as a cook and attended Sunday school while incarcerated.

In 1909, when John Montgomery was first accused of murdering Nelson Daugherty, he and his brother paid for his legal defense with a deed conveying 75 acres of Kingdom property, that they had likely inherited. It is not presently clear how they came into posession of the acreage they used to pay attorneys W.G. Colson and John H. Hurst, or how that conveyance may have impacted the Kingdom.