Age: 17
Hair Color: Blue
Eye Color: Green
Height: 5"8'
Favorite Food: Instant Noodles
Likes: Bottle caps, instant food
Pok�mon He Has Owned: Growlithe (left behind), Magikarp (evolved), Gyarados (had to leave near Vermilion City) Koffing (evolved), Weezing, Victreebel (Jessie made him trade it), and Cacnius.
James' life began very differently to Jessie's, with, as far as we know, no previous family involvement with Team Rocket. He was born into a very rich family, and many years lived on their large estate not far from the archaeological site, Grandpa Canyon. This is one possible factor leading to James' interest in bottle cap collecting, assuming that he witnessed some of the digging as a young child and was then encouraged to try it for himself. Living on such a large estate, it is very possible that on his first dig, he did discover a bottle cap, and his interest was sparked. Over many years, James' collection of bottle caps has grown, been destroyed or lost, and rebuilt again, thus providing an insight into his activities in his spare time. But, let's not delve too deeply into that just yet, as its still many years in the future.
From a very early age, it was decided by James' parents that he would marry a young girl named Jessebelle. She was extremely refined, and would often give James lectures on "how to do things properly", to make him a suitable, and perfect gentleman to be her future husband. The classes could often lead to violence, if James failed to co-operate. This explains James' coward-like behaviour that we see now. Being subjected to this at a very young age made James feel weak, weaker than everyone else, and gave him a reason to fear people with some sort of power over him - pain, either emotional, or physical. James' parents greatly approved of this refinement, despite the fact that James made it quite clear that he strongly disliked it. This is likely one reason why he formed such a strong bond with his grandfather, who would take him on trips to Johto, teaching a variety of things which James found considerably more interesting than Jessebelle's correction classes. It is also likely that James' "grandpapa" lived in Johto, which would explain two things. One of which being the fact that James mentions this relative far more once the gang reach Johto, three years into Jessie and James' quest to capture Pikachu. The second is the fact that his grandpa knew about a variety of different Johto Pok�mon, virtually unheard of in Kanto, such as Sunflora.
Looking further at the effects of Jessebelle and the "James" she created, the emasculation that occurred in James has resulted in an adult that many consider to be gay. This is based on his "weaker than everyone else" and generally fearful and cautious approach to life, although other factors have influenced people to think this way. The fact that Jessie and James have been friends for many years yet there have been very few signs of anything more than friendship shown is often used against him. Cross-dressing, and even his voice have been criticized by many, although looking deep into James' background and upbringing explanations can be found for nearly everything. James' first experience with girls was Jessebelle, and, as this was a complete failure, it is very likely that this plays a big part in keeping him from developing any other relationships, especially with Jessie, who resembles Jessebelle in both looks and personality. However, the fact that James has remained friends with Jessie for this large amount of time suggests that this does not play heavily on his mind. It is therefore easier to conclude that James has a fear of relationships, because of the supposed commitment he will have to face, based on what he had been shown during his time with Jessebelle.
Cross-dressing, a very interesting characteristic, and is usually one of the first to be used against James being straight, but there are reasonable explanations. The first and most obvious is the fact that they are disguises, and what better way to disguise your identity than to change your gender. The second is that of rebellion. He was brought up, and told exactly what he could and couldn't do to become the perfect gentleman. Now that he is free from the restraints of his parents and Jessebelle he wants to show that it doesn't matter what he wears, he is the person he wants to be. James' cross-dressing occurred most frequently in the original Indigo League series of the anime, and in the later series he rarely, if ever, dresses as a woman, and this points to another similar explanation, one of exploration. Living at home being trained as the perfect gentleman he was not only too young to have any strong feelings of sexual preference, but would also not have been allowed to voice them even if he did. After leaving his home and joining "The Bridge Bike Gang", he would have been unable to explore his sexuality, due to the inevitable peer pressure surrounding him. Therefore, in all of his life, his first opportunity to explore his feelings would be during the true freedom he experienced on joining Team Rocket. During this time, it seems he tried cross-dressing, although feelings for girls were still clear, such as his references to the "Ghost of Maiden's Peak". Towards the end of the first series, and thereafter, James' cross-dressing ceased for the most part, suggesting that on exploring his feelings he came to the conclusion that he was a heterosexual. In this sense, he has matured, and no longer engages in this kind of questioning, usually more commonly experienced during childhood.
Subjected to this restrictions and the high expectations held for him living in such a high class family, James ran away. Previously, James had attended the Pok�mon Technical School, where he became friends with Jessie, before the pair failed exams after staying awake the night before partying. As the two became friends at this age, it is possible that the running away to join the Bike Gang of Sunny Town was an organized event, and not a lucky coincidence. This was a large and bold step to take for people of such a young age, suggesting a stronger form of closeness and trust present in the early relationship between Jessie and James than your average friendship.
In the Bike Gang, James was known as "Little Jim", as he was the only member who needed training wheels to ride a bicycle. This offers further insight into his upbringing. He clearly was not brought up as you would expect a child to be, playing with his parents, and evidently skills such as riding a bike. His parents obviously favoring the teaching of etiquette and other skills which overall would be of little use to James after following the path he has chosen. This, therefore, has also contributed to James' lack of masculinity (I'm talk about his personality, people). He never had any strong role models, male or female, when growing up, the difference in personality between him and his parents making them virtually incompatible. This resulted in his character being shaped, as speculated earlier, from a young child's natural instincts and the fear he was presented with early on, explaining the childish nature still displayed today. His close friendship with Jessie did have some effects though, and certain aspects of her personality rubbed off and him, and so over time James developed more confidence in himself and overall more confidence in general, although the base cowardice remains.
Another aspect of his character is his gullibility, clearly shown in his repeated encounters with the Magikarp Salesman. One would not expect this behavior from someone with such bad experiences and lack of trust in the home, but an explanation can be found. Joining a gang, in his case the bike gang, it is not uncommon for all members to feel like a family, and so would trust and rely on each other. This would have therefore allowed James to gain more trust in people, and this would be taken even further later in his life. Joining Team Rocket, James found himself trusting and relying on Jessie and Meowth, not just to be part of a gang, but to survive, facing far more dangerous and demanding situations. Therefore, in complete contradiction to his earlier life, trust in people became a key element of his life.
Not brought up in the hostile environment that Jessie experienced, James has retained some morals that she still lacks. A certain degree of politeness and respect is still present, likely imprinted in him during the lessons from his parents and Jessebelle. This is most clearly shown in the gratitude he shows towards Ash, Misty, and Brock on various occasions, notably his refusal to battle in "The Stun Spore Detour" after Misty aided in an sick Jessie's recovery.
Other than this, very few details of James' mysterious past have been revealed, although a few minor facts are none, which I will list for you now:
James' home was decorated with expensive art work
He suffers from allergies to Bulbasaurs' pollen
He likes his steaks rare
He enjoys caviar and crackers (likely from his time at home)
He has placed personal ads