Also, the guy who wins the first time is always ahead. The worst he can do is break even. When he quits or the game ends, he'll be anywhere from $0 to $900 up, depending on where he is in the cycle. Everybody else is always playing catch up.
This is a very good point.
If anyone but the last person quits or if this scheme (for lack of a better word) ends abruptly, there are going to be a lot of hurt feelings. I don't see this ending well.
Tough call, but if they were my direct reports I would probably consider telling them to knock it off before someone gets stabbed in the parking lot.