[JaBlue]

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My recommendation is to introduce him to chess, or get someone to introduce him if you don't know how to play. Perfect for a smart, uncoordinated, and shy kid. Something competitive that he has a natural tendency toward, a brainy activity. It gives him a setting to socialize with other kids, and if he goes to a school with an active chess club, those kids (and their parents) eat that stuff up and will encourage him. Scholastic tournaments are madhouses, and they give out trophies to just about every kid. Some of the trophies are bigger than the kids! It's a lot of fun, and it's not just for geeks.

I've taught kids like your brother how to play chess. The really shy ones who get good at it eventually come out of their shells when they realize they can be good and win at something. It gives them confidence. Then they decide that if they can do well at chess, they can try to do well at other competitive things, like sports.

Then when he turns 21, he can ditch chess for online poker, naturally. Good luck.

ScottieK

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This brings up a good point.

His mom said he liked chess and I am not bad (1900 or something before I quit competitive) so I played with him and tried to teach him stuff and get him to think about the game, but during our game he revealed a really terrible current trait:

When he knew he was going to lose (i.e. just by playing against me), he gave up before even trying. I would guess that because things come so easy to him normally, he's liable to give up whenever something is a challenge. Of course it could be that he just doesn't like chess, but the way he wore his emotions I really doubt that.

So I also wana develop some kind of work ethic and competitive instinct.