Will the Red Sox give Johnny D. the contract he desires? Considering that $20M is earmarked for Manny, $13M for Schilling, $10M each for Renteria and Varitek, $8M for Clement, $7M for Foulke, $6.5M each for Ortiz, and Nixon, the Sox have $81M committed to just seven players, and if they give Damon a contact worth only $10M per season, that's $91M going to eight players on a 25 man roster. They'll still have 17 other players to pay.
It's conceivable that the Sox might chose a less expensive option like Torri Hunter or Juan Pierre in center for the short term, while Jacoby Ellsbury, David Murphy, and Brandon Moss continue developing in the minors.
Damon wants to return, saying that he fell in love with Boston and it's fans, but he is in his prime and this will be the last long-term, big-money contract he'll ever sign. With that in mind, he wants to get paid - big time.
One important consideration that Damon should, and likely will, keep in mind are his marketing opportunities as a member of the Red Sox. Boston is a large market where Damon has become a sort of folk hero. He's had numerous endorsement deals in Boston that he wouldn't have gotten elsewhere. New York and LA are filled with stars - athletes being just one of a variety. Damon is a standout in Boston, and not simply one among many. Those endorsement and marketing deals as a member of the Red Sox will push his earning potential upward by millions of dollars over the life of the contract. And playing for such a consistently competitive team with such a large national following also gives Damon tremendous national marketability that he wouldn't receive in many other cities throughout the country. That creates a peripheral, or even integrated value that is worthy of consideration.
There's a good chance that we'll have our answers within a month, or certainly by Thanksgiving. If Damon and the Sox can reach a mutually satisfying agreement, then everyone will have something to give thanks for.
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