Why do you think he learned to play mario kart well? Ever hear of "making the game interesting"? Old boy is a hustler, he'll lose the first few games, then say he needs stakes, then bet his "presidential" tie. When he wins, he'll just tell his victim that they need to take off something to keep it fair.

His victims are too young to notice he's breaking out the pro moves, drifting/slipstream/stunt boosts/etc.