Reading the Letterman-thread got me thinking. How is it really possible to blackmail people if they cooperate with the police? How can you get the money without risking getting caught? At some point you have to meet up to collect the money.
Have them leave the money somewhere inconspicuous, at least that’s how they do it in the movies.
And then the police hide there and catch the guy when he picks it up…
The whole point of blackmail is that the victim doesn’t want the information to come out, so the blackmailer doesn’t expect them to go to the police (or else he wouldn’t even attempt to blackmail them). The blackmailer counts on the fact that the only person who will be involved is the victim, or confidential agents of the victim like a lawyer. Once the victim tells the police, and the blackmailer is apprehended, the secret will inevitably come out. The police will have to announce the arrest, and the blackmailer is likely to spill the beans in revenge against the victim for ratting him out.
Well I would have NEVER done it with a check. What an idiot.
I guess you could do things like exchange gold that you could hock, but that’s awkward 'cause pawn shops don’t give you anything.
For instance, if you had $10,000 gold chain he could give it to you and you could maybe hock it for $1,000. That’s all legit. Well except for the blackmail part.
There’s always ways of laundering money but it usually costs to do this, so you’d have to ask for a LOT more to get you’re money.
Say you want a million bucks, it might cost you 25% in expense to launder that money so you’d wind up with only $750,000. So you’d have to ask the person you’re extorting money from for $1,250,000 so your net is a million.
Usually blackmailers don’t think that far ahead. I read the guy did it 'cause he has money problems. Now he’ll be clothed, fed and housed all at government expense for up to 15 years. 
Minor nitpick.
If it costs you 25% in expense to launder money and you want to net at least a million dollars you would have to ask for $1,333,333.34.