Should I stay in a game that involves betting on a fantasy football league?

Question:

Hi Jeffrey,

I have a question for you regarding a gambling situation I'm struggling to decide on.

One of my friends has a fantasy basketball league with ESPN.com where people can have basketball teams with particular players from the NBA and they compete based on stats and points to win. His league requires everyone to put in a sum of money to play and at the end of the year, the winner of the league gets that sum of money. He has, however, offered to pay for my amount because I had already expressed to him my discomfort with playing for money. I could basically play with his league for free and at the end of the year if I win the league, I wouldn't win the money prize, but he would donate the money to a charity of my choice.

I did play last year, but I've been invited to play again and currently am part of the league. I have two problems with it right now. First is that it is still a form of gambling and, secondly, I think it's against the rules of ESPN's fantasy basketball as they say any form of gambling is prohibited in their rules section.

My friend has expressed that this is a way we can keep in touch as friends. He lives a long distance away from me, though he is someone I've known since I was in high school. I don't talk to him much, but we do talk about sports from time to time. This would be a nice way to maintain a friendship and have fun, but I struggle with the gambling part. Even though I'm not directly giving money and though I wouldn't win the actual money prize, except that it would go toward a charity, I still feel discomfort in that I would be indirectly associated with allowing or supporting the gambling that would be going on in the league. So I'm wondering what your advice would be for me? Should I play in the league or should I leave it and tell him my thoughts on why?

Thanks for your help.