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It's only human to want to avoid taking the game out of the player's hands, but, "You can't make a silk purse out of a sow's ear" and sadly a jerk will stay a jerk until he's made to stop being a jerk.
For what it's worth, when dealing with the guy who just won't stop with the smart apple comments, you can take him aside and offer him a choice; coach his team from the sideline and keep his comments to himself, or say whatever he wants, whenever he wants, as loud as he wants from the parking lot.
Of course you have to be willing to absolutely back that up.
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