L.L.
I think the pay it forward is fine IF this kid will eventually be driving but if he is going to continue to ride with someone else, yes he should chip in towards the gas. However, as far as him being a freeloader, your son offered him a ride to a place he was already going and would still going whether or not this kid went. On the occasions that he takes this boy home yes, the PARENTS should give him some money for gas. Did your older son ever ask this kid to pitch in for gas or did he just assume he was a freeloader because he never had the courage to ask him for money? I think that the best way to handle the situation would be straight up, if the kid asks if he can ride with son #2 to practice, son #2 tells him, "Hey Man, I don't mind giving you a ride but I need some help with the gas because it has just gotten so expensive I can't afford it."