if his parents/family were part of the 1% why would he simply not pay for his medical costs out of pocket?

At 26 you’re on your own insurance and he was a right wing tech bro, it’s a safe assumption he had the cheapest insurance, got hurt and bailed out, then got the “good” insurance and found out it’s shit too.

He had major back surgery and then other shit, it could have went over a million, and the wealthy stay wealthy for generations by understanding wealth is finite. At a certain point they may have cut him off for deductibles and/or insurance capped out.

He could just be pissed Doctor’s won’t investigate the issue, because insurance told them not to.

There’s a lot of reasons to be pissed at insurance, and a lot of reasons health issues bankrupt even well off families.