>>41171392It varies. For example,
Red's Lapras was new when he got it, because it was an untrained kid gifted from a scientist. Red tried to use it against Giovanni due to type advantage, but it lost because of its inexperience, so Lapras constantly regrets being so weak and helpless compared to the rest of the team.Or take [spoilers]Karen's Umbreon. It used to be a cute Eevee under a different owner, but it got disowned and abandoned because it evolved, and its red eyes caused its owner to be terrified of it, calling it a demon.
The key part of it is to have an excuse to give flashbacks in the middle of the story, and the degrees go from regrets of losing previous battles, to traumatic experiences.