Has anyone ever had problems collecting from a bookie?

So I use a bookie to make sports wagers. Never met the guy. I was referred by a friend. The way it works is I use a website to place the wagers. If I'm down money at the end of the week I send him or check or deposit into his bank account. If I'm up he deposits money into my account. Anyway I asked to cash out some money on Monday and he said he would do it that night or the next day. Well it's been 3 days now and I haven't heard anything from him. Since then I've doubled the amount I wanted to withdraw with a lucky streak. I'm not too worked about being paid, but just curious if this has happened to anyone. Seems like it would be really stupid of this guy not to pay me since I know a lot of his information

sometimes it may just take a few days to hit bank account

Yes, Artie Lange has

I do the same thing with my bookie (website, bank deposits). We'll typically wait until the payment owed builds up to $1k before requesting a deposit (in either direction), unless otherwise requested. Upon the request, we allow each other 1 week for the payment to occur before the nagging starts, and it's rare for it to get to that point.