Yes, gamblers do win but it is very seasonal. There is only a little chance for every gambler to win and I think it depends on the game that they are playing if it is base on luck or their skills.
And I am talking about regular gamblers who I mean are active in chat almost daily so it's not like they made profit once and stopped gambling, they are active and gamble almost every day so how some guys are managing profits while others are failing?
Most of the time, those who are active in chat almost every day doesn't mean that they are playing every single day. They have their own reason but it is not like what you think.
And another possibility, gamblers who are active in chat are more likely to have their remaining balance on their account so that they are active.