Maybe I am overestimating what he earned in a year. Tried a quick search to figure out what % of his take home income this was.

I am not sure at what point I would start to consider 4 months in jail for insider trading “worth it” (again this was a plea deal, could’ve been higher).

If all your personal wealth is tied up in a single company’s stock then you obviously run a risk of losing it all. The solution to that is diversifying your portfolio, not insider trading.