James grew up in a very small town in western Wisconsin, and spent a lot of time on his uncle's dairy farm. He was unfortunately the victim of physical and psychological abuse from his father starting at an early age. This escalated further when his parents divorced when he was 10 years old, and continued into his late teens at which point his father realized he was old enough and big enough to fight back. As a teenager, when he wasn't doing schoolwork or performing with his high school choir he spent most of his time taking care of his mother who retired early on disability due to severe mental health issues. He was essentially a parent to her and handled the cooking and cleaning for the house as well as making sure that she was eating, getting out of bed, etc. He also briefly attended the local community college where he lived and was majoring in Hotel and Restaurant management before he had to drop out as he couldn't handle the work load on top of other responsibilities.

Shortly before moving to Los Santos, James received a call from his sister that her son (James' nephew) had come home from their father's house badly bruised and not wanting to talk about where the bruises came from. This wasn't the first time that this had happened, and James recognized this as exactly the way he would act when asked at that age after his father had abused him. James went to his father's house to confront him. What started as a shouting match between them quickly devolved into James tackling his 70 year old father to the ground and punching him over and over. Eventually he heard his father barely get out the words "Please... stop....".

James responded by stopping as requested, however instead of letting the old man get up he reached to his waist and drew the pistol he always had holstered. James drew the gun, placed the barrel directly against his father's forehead between his eyes and pulled the trigger whispering "Never again".

After that, he picked up the single bullet casing, went to the garage, and got the gas can that his father kept in the garage in case the lawn mower ran out of gas in the middle of mowing the lawn. James took the can inside, dumped gas all over the house, then struck a match and dropped it lighting his childhood home ablaze with his father's corpse still laying where he shot him. He then left the house, packed his things, and headed to Los Santos where he now resides.