2 years ago I was in a Fantasy Football league at work, organized by one of my co-workers (for ease of the story, lets call him Bob).
It was an expensive buy in, $1000 a piece in a 12 team league with large payouts going to the first and second place teams.
I didn't place in a spot where I was going to be winning any money, but the guys who did win were obviously excited about the big checks coming their way.
Well, the first week after the season ended they went to Bob, who organized the league, and said "So when do we get our checks?", Bob said, "Oh, by end of this week. I'll bring the checks into the office."
Week 1 goes by, no check from Bob.
Week 2 ... Bob said he mailed the checks, which made zero sense, but Week 2 goes by and no checks are to be found. Bob claimed they must have been "lost in the mail".
Week 3 goes by, still no payouts from Bob and by this point the people who won are pissed. The rest of the people involved in the league are annoyed too, because we all invested money in this league.
Basically, it's becoming obvious that Bob didn't have the money.
Week 4 comes ... the two winners approach our boss, who was also in the league, and explain the situation. They ask for advice. Can they go to the police against Bob? Can they sue Bob? Can they dock Bob's pay?
The boss calls Bob into to the office with the winners and the rest of the people in the league. In front of everyone the boss asks Bob point blank where the money is. Bob says, "Oh, well it's in the bank. I just need to get them a check.", my boss says, "Okay, we're all going to go to lunch together today then. Before we go to lunch we'll go to your bank and you can withdraw the money. We'll make the trip together."
Bob's face goes white and he says, "Oh, well I can't do that. The account is in my wife's name, she needs to be there to withdraw the money."
My boss says, "Great, call your wife right now, put her on speaker and tell her to withdraw the money today."
Bob says, "Oh, my wife's out of the state on business. She can't do that, but I promise I'll get the money."
At this point my boss is pissed and everyone in the room is looking at sketchy Bob with disgust. My boss tells Bob very matter-of-factly, "Here are your options Bob. You can either solve this with us right now and be honest, or we can call the police and have them sort this out."
Bob starts to cry in front of everyone, claiming he had the money but he spent it over the course of the season. He had $400 in his bank account total and couldn't pay anyone anything.
My boss says, "Okay, well here are your choices Bob: Option 1) Every week, when you get paid, you will give 25% of each paycheck to the two winners until each of their balances are paid. You will do this weekly in front of me and we will keep a running tab on the amount owed. Option 2) I will fire you right now for theft and call the police. You will leave this office today in handcuffs."
Bob starts crying uncontrollably and agrees to the payouts. Basically Bob lost 50% of his paycheck for a few months until the balances were paid in full.
We still do Fantasy leagues at work, but now all money is paid in cash and kept in a safe in my boss's office (which has security cameras). Bob is not allowed to participate.
Bob still works for the company, but is pretty much regarded as the dick of the office. It's sad, because he was rather well-liked before all this went down.