Dark days (2005)
After trying to commit sucide (in water or Stillness, unsure which yet), James is recovered from Leon as he is driving by. James, being too out of it, couldnt describe, nor tell Leon why or how he ended up in the lake, which ended up with him being forced into the hospital.
Originally, Leon thought it would've been the end of the interaction, if the hospital hadn't called due to James having no paperwork or anything related to him, other than the missing persons report on both him and his wife, Mary. Though, these reports were old, to where James was considered dead, with most of his things being terminated, including his job, any credit cards, his homes and all of his belongings. Leon ended up guilting himself into taking James in, just to try and get James back up onto his feet, even if Leon's job, USSTRATCOM: Anti-Umbrella Pursuit and Investigation team, called James a liability. In addition to him being a liability, the fact that James had refused to say how or why he was alive was causing suspision, including possible bioweapon accusations, as his scars matched a few documented bioweapon scars.
Unfortunately for James, The state of Maine (and all others) had declared him dead years ago, so any sort of insurance fund was long gone. With the stress of having nothing to his name and the events of silent hill, it broke him rather easily, making him attempt again, which made Leon force James into a psych ward, directly during the harvardvillie incdent, cutting nearly all contact with James.
James, thinking he was abandoned by his only helper, ended up in his mind even more, with pills and therapy barely working from his avid defiance for it all, with any and all possible progress dissaprearing due to being in a hospital itself and hallucinations refusing to ease no matter what was taken.
When Leon came back, visiting James after a few days of hesitation, he quickly saw the state of James and his worsening state, and quickly pulled him out of the ward, though keeping him in therapy. James, assuming he did something wrong quickly devolved into a fauning responce, trying to please Leon as best he could.
Sunset (2006)
Leon's drinking effected James though, often Leon getting him drunk with James refusing to say no, out of fear of being abandoned, percived or not. Involuntarily, they both ended up leaning on eachother to worsen their alchol addictions, even when Leon was actively trying to quit smoking. This came to a breaking point when James drunkenly confessed how he killed Mary, turning into a (mostly) onesided screaming match while James dissasociated. They didnt talk much after that, acting more as strangers than two people living together.
Eventually, despite James' confession, Leon refused to give this information to the police, or report it, instead going off to try and find a better therapist, for James, finding a rental and managing to get James enough to try and get him back on his feet, including the ability for him to get a job again. Making sure that James was away from Leon, knowing it'd do more damange than good for the both of them.
Pitch
DayBreak