I'm sure there would still be people who would give him their money (likely less-than-honest people themselves, knowing he was a con-man and hoping to get in on

I'm sure there would still be people who would give him their money (likely less-than-honest people themselves, knowing he was a con-man and hoping to get in on the game). What I mean though is that obviously all of his finances would be closely monitored (you could probably forbid him from actually being in charge of them), everything would be constantly audited. If he so much as bought a new Honda Accord, it would be taken, sold, and the proceeds would go to pay back his debts. Basically, just like he isn't allowed to run a business or manage his own finances now, when he is in prison, he wouldn't be able to while outside either. Literal prison walls don't really add that much to our ability to control those things.