You are allowed to offset your losses to the extent of your gains so, since, he ended losing monies, he probably, did okay tax wise. Atleast, he did not have to pay any huge tax bills.
If he paid his mortgage, he would atleast, have recouped the credit card and home equity loans and if he decided to pay off his mortgage in full, he atleast, would have lost much, much less. Not the full $1,000,000 he ended up with. Instead, it probably, made him think, he was a very good trader who can turn that into $5,000,000. Why stop now?
That's why he'd have lost it in any timeline. No concept of Risk Management (obvious by how quickly he rose to prominence) and his greed would not allow him to take money out because that would mean less monies to compound. His greed and lack of RM made going broke, and at a high speed, an inevitability.
Yup.... To Coddle is to Cripple... Providing these ignorant kids with trophies for failing.. finishing in last place.. while they were growing up... Eventually all Snowflakes melt & fade away!