Explain how this presumed gangster thing my brother saw works

General Questions
#1

My brother was at this bar Saturday night and in comes a fellow and gives the bartender a bunch of receipts. The bartender browse through the bundle and says with a gesture, obviously unhappy about this, “You guys are ruining me…!” He seemingly registers the numbers in the counter, keeps the receipts, takes a lot of cash out of the register and gives to the man, who walks out again.

The man with the receipts is of the ethnical group who “run things” in this town, which reinforces the suspicion that there was a gangster thing going on (though, it should be mentioned, the vast majority of said ethnical group are upset with the criminality of some of their peers).

But if it was protection money or something of the kind, how would it work: The receipts on the on the one hand, the register and the cash on the other? What’s the “economics” behind this barter?

#2

I didn’t realize reimbursing people for purchases automatically means criminal behavior.

I myself have many times done the exact exchange with people working for me. If someones out in the field working and needs to go pick up a part, they go to the local hardware store or what not and buy it with their own money. When they next see me they hand me the receipt I give them the cash. With past employees I’d had some that didn’t bother turning in the receipts till they had a few hundred dollars worth. This drove me nuts for a number of reasons.

#3

If it was protection money, he wouldn’t have been submitting receipts. Protection is done under the table, being illegal and all.

#4

As someone who runs a small business, it’s always easier when people get paid (be it handmen, employees with their paychecks, vendors looking for payment) a little here and there rather then all at once. This guy asking for what may have been several hundred dollars all at once instead of a hundred once a week may have meant the bartender couldn’t payout someone else later that night. Or that he would have a hard time making change for the next hour because the guy just wiped out all his 10’s and 5’s or…it might have just been a joke.

#5

If it was ‘protection money’ or anything illegal. Having receipts is a good way to keep under the table money above the table. If the bartender has to skim $300 out of the register, he needs to find away for it to disappear. Either by selling drinks and not ringing them up, making refunds into his own pocket or some other method. Even if he’s the owner, he’s still got to deal with the IRS if he would ever be audited. If he’s got receipts for things that a bar would need (brass polish, random supplies from a hardware store etc) this makes the problem go away. If he was in fact “paying for protection” he may have told the guys that it would be alot easier all around (or maybe that he could get them more) if they give him receipts so he would be less likely to get caught be the IRS/FBI skimming money.

But my guess is just that they were some handymen working on a job for him and maybe he asked them to stop by during business hours (when he had cash) to get paid.