Quote from atticus:
Stupidity of this magnitude is rare (notional impact), so being destitute will certainly be punishment. Who's the bigger fool; the fool who leads or the fool who follows?
You have a large, six-figure gain in AAPL shares (vast majority of your net worth), you're out of work, and you proceed to cover and take the cap gains hit and then invest in upside calls! Excelsior! Guy went broke and has a huge tax liability. Rare ignorance.
I knew a high stakes poker player who was encumbered with the tax on a 1.2MM take home from online play. Lost it all in the new tax year before he paid for the prior year liability and then wondered why he couldn't offset 1:1.