A lot of guys just are guys who worked hard half their lives and ran up a tab they couldn't pay
That's very true. I've made similar posts in the past, but I can't tell you how many guys end up "with" someone because they can't bring themselves to bet against the Giants or Jets.
The fact is, it's debt that will most often bring you into close proximity to these guys (if you didn't grow up with them), and that weekly contact breeds familiarity, which often leads to to trust and business relationships. A one-time brokester ending up with his button is a lot more common that you'd think (and sometimes they're
still broke
after getting straightened out

).