James

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Section heading
An only child of millionaires, James was forced to endure formal society while growing up. Often having to take part in numerous lessons and activities he had little to no interest in, he eventually began to grow weary of the rules and standards that appeared to be ever-present within the upper-class.

At a young age, he was engaged to a girl named Jessebelle. It was revealed in The Treasure Is All Mine! that he wanted to marry her at some point but he changed his mind after he saw how controlling and overbearing she was. Unable to stand her, he ran away, leaving his lavish lifestyle as well as beloved pet Growlithe, Growlie, behind.

He then enrolled in Pokémon Tech, a Trainers' school, where he met Jessie, and subsequently failed and dropped out. After this, as revealed in The Bridge Bike Gang, Jessie and James joined a bicycle gang in Sunny Town, where James was known for using training wheels, acquiring the nicknames "Little Jim" and "Trainer James".

Due to conflicts in canon between Kanto and Johto episodes and the special episode Training Daze, what happened between James and Jessie after the bike gang is unknown. What is known, as shown in the special episode, is that they joined Team Rocket separately and were on initially unfriendly terms after being grouped with Meowth but they quickly made up and became good friends

Personality
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Pokemon
As the standards of the Team Rocket organization dictated, James was first shown with a Poison-type Pokémon. However, James seems to have a fondness for carnivorous (or at least dangerous)  Grass-type   Pokémon, owning  Victreebel ,  Cacnea ,  Carnivine  and  Amoonguss. It was shown during a flashback in  Cream of the Croagunk Crop!  how James, as a boy, found  Carnivine  in the  Great Marsh. It was trapped in the mud and James rescued it, the two forming a bond of friendship. The capture of a  Cacnea  early in Hoenn furthered his apparent preference for Grass types. Often, when going into battle, his Grass Pokémon will show great affection towards James, which usually results in pain for him since all of them either have sharp teeth or spines.