Clearly he is far nastier than you.
I choose this way because wealth and power are important to him/her, taking all that away from them and watching him/her struggle to live a normal life with 9-5 job and doing all the stuff that he would never have done as a trust-fund baby would be difficult enough for him. And if I see him slowly starting to build something for himself, I can step in and use my influence to knock him back down to square one again.
Back when we had the first Probe I wanted to hang him from a meat-hook in my fridge and feed his pet Ausar to him piece by piece, but I decided a long term psychological torment was a little more entertaining (and legal) than a simple week long body horror fest..