Chasing6
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Cherry would lose in checkers.Or Jerry thinks he can get him to re sign cheaper if there are no teams interested in him. By not playing, it's impossible to drive his price up. Everyone will think he's so bad in practice that he can't get on the field on Sundays.
This is a classic example of Jerry playing chess while the rest of the league is playing checkers, or at least he will sell it that way.