I actually think the wording of your original post was just fine.I guess some people are taking my wording a bit too literal, my fault. This wasn't meant to be a philosophical debate. How about this:
Get a ball from a guy who plays a ball better than you?
OR
Give a ball to a guy who plays a ball worse than you?
This second version is different, because you never mention anything about the evenness of the match. If money is at stake and the match is tilted to one side, of course I'd pick the option that would fill my pockets in the long run, regardless of me giving or getting weight.
So the matches being even is an important requirement. To reiterate my previous post, if the matches are set up to be perfectly even, then I'd rather reap all the psychological benefits knowing that I'm the superior player.
But having thought of it some more and reading other posts, there is a benefit to being the inferior player provided that you could learn from playing a superior opponent and improve your overall play in the future. But the amount you could learn would be based on the differences in skill level. The bigger the skill gap, the greater potential for improvement by the inferior player. If your opponent is the same as you but simply a much better potter, then there wouldn't be much learning you can get out of the match.
So to sum things up, given that money is at stake (it's a gambling match and not a friendly match up)...
1) If the matches are set up to be perfectly even and the difference in skill is small such that the inferior player won't improve substantially by playing the marginally better player, I would rather be the superior player and get all the psychological benefits knowing I'm the better player.
2) If the matches are set up to be perfectly even and the difference in skill is large such that the inferior player could improve his play by playing the superior player, then I would rather be the inferior player and improve my play in the future.
3) If the matches are NOT set up to be perfectly even such that one has a slight edge, then I would rather be the player with the edge and come out richer in the end.
I think I got most of the bases covered.
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