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I doubt he retires with them unless because of injury. Not many quarterbacks stay with the team, because quarterbacks stay in the game too long. The team has plans for the future and most quarterbacks (i.e. Favre) stay past their prime. Montana was never the same in KC, and there's many examples I could think of. Warren Moon in Houston, etc.
He will resign no matter what. Pittsburg loves him, and if he leaves they will not be happy. Unhappy fans = less mula. So they will pay him whatever he wants, even if they have a tough time deciding, cause if the lose Big Ben, then they lose money