Vaclav
Bronze Baronet of the Realm
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Yeah the flashback a few episodes was her visiting after they already broke up and his "condition" was in full effect and they pretended the power just went out.
Anyways, Chuck definitely would overcome his mental condition when it involved bringing Jimmy down. It does show just how much deep seeded resentment Chuck had for Jimmy, but doesn't explain what caused his condition in the first place. I'm really hoping we get an answer to that.
As someone who's had to deal with a ton of hypochondria over my years (both personal - with the woman and possibly I [my cure was psychiatric after all - none of my head docs have said hypochondria though] - and professional with the many employees I dealt with) - one of the way's that hypochondria ends up demonstrating itself seems to be a "cry for attention" type thing in response TO OTHER people being sick legitimately or not (and it seems people that think/know someone else is faking are more likely to).
With that in mind I'm imagining they're going to characterize his fall into the "condition" as a cry for attention after Jimmy pulled a huge stunt. Probably in some rough situation, like one of their parents dying and giving all their attention to Jimmy over one of his normal bits of trickery.
After such an amazing characterization explaining Tio's condition this season, I'd be disappointed if it wasn't explained in a manner like that with a ton of logic behind it. I was VERY impressed with how they handled Tio's crippling.