Ohh, if he was actively looking for a loss then he might've been on the hook with some bad people who were lending him the money and he was laundering them. You

Ohh, if he was actively looking for a loss then he might've been on the hook with some bad people who were lending him the money and he was laundering them. You see, laundering is all about loss and looking bleak in the eyes of IRS (or equivalent). In the end he might not been an active asshole but just another victim.