Derek Jeter: Is New Contract Biggest No-Win Deal for Yankees in Sports History?

Elliott Pohnl@@ElliottPohnl_BRFeatured ColumnistNovember 29, 2010

Derek Jeter: Is New Contract Biggest No-Win Deal for Yankees in Sports History?

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    Derek Jeter continues to seek a massive contract from the New York Yankees, who are showing no signs of caving into the future Hall of Famer's demands.

    According to multiple reports, Jeter is seeking a five or six-year deal worth over $20 million per season.

    The Yankees have countered with a three-year contract worth a reported $45 million.

    Let the bargaining begin.

    It didn't take long for negotiations to go public, with the Yankees openly encouraging Jeter to test the open market.

    It sounded like a dare, and it was.

    Don't expect there to be any teams willing to meet Jeter's asking price.

    In the end, the Yanks appear to have the best chance to sign Jeter.

    But should they?

    If they simply let him walk, Brain Cashman and Hank Steinbrenner could face a very harsh public backlash.

    If they sign him, they risk keeping him on the payroll as he enters his 40s.

    It's a classic catch-22 situation that threatens to damage the shiny luster of the Yankee franchise.

    Could the Yankees possibly escape the Derek Jeter negotiations in a positive light?

    Let's play a little point-counterpoint to help arrive at a conclusion.

5 No: Yankees Would Look Courageous for Letting Him Walk

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    In an era when the inmates often seem to run the asylum, letting Jeter walk would be a victory for franchises everywhere.

    Instead of caving to the excessive contract demands of a player who could finish his career in a platoon, the Yankees would be taking a stand.

    It might not be a popular move, but it would be a win in the long run.

5 Yes: Yankees Must Cater to His Star Power

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    Think of it as a lifetime achievement award.

    Despite his career-low batting average last season, there are plenty of Yankee fans who feel the captain is owed one final deal by the Yankees.

    Somehow, Hank Steinbrenner crying poor just doesn't fool the masses.

4 No: There Will Be Other Great Shortstops

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    Instead of pouring money into a player who will need to be replaced in a couple years, the Yankees could choose to go after a decent replacement and look to the future.

    Without any great options in the farm system, it might take a big free agent move to replace Jeter's production.

    Ultimately, Yankee fans would be happier to embrace a star of the present instead of a falling star from the past.

    If only there was a decent free agent shortstop on the market heading into 2011.

4 Yes: Jeter Is the Most Polarizing Yankee in Years

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    He might not be a great shortstop at age 36, but Jeter still has plenty of star power.

    His statistical accomplishments are already Hall of Fame worthy, even as he continues to seek his 3,000th career hit.

    But his true worth to the Yankee organization can be measured in World Series' titles.

    It's difficult to expect fans to not be at least somewhat influenced by loyalty.

3 No: Keeping Mariano Rivera Might Be More Important

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    For some reason, the other Yankee hero who also needs a new contract continues to fly under the radar.

    In the end, keeping Mariano Rivera might be more important to the Yankees' immediate future.

    With no reliable closer in-house, New York would have to shell out millions for a replacement to Mo.

    What happens with Jeter could eventually take a backseat to Rivera's retention or retirement.

3 Yes: Blinded by Loyalty

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    It's easy for fans to get blinded by a sense of loyalty, and internally, the Yankee brass might be bristling at the idea of letting him walk away.

    This important factor could eventually make the two sides agree on a contract.

    At this point, there is little to indicate Jeter's production merits the salary he will command.

    That doesn't mean he won't get what he wants in the end.

2 No: One Move Won't Define the Franchise

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    Given the reactionary nature of today's media, what happens with Jeter will be front page news for days.

    It will come to define Brian Cashman and Hank Steinbrenner in the present. 

    But not forever.

    In the end, whatever happens with Jeter won't come to define the mystique of the Yankee franchise.

    One way or another, the Captain will be sporting a Yankee cap in Cooperstown.

2 Yes: Since When Will the Yankees Not Overpay?

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    The idea that the Yankees can't afford to pay Jeter more than he deserves isn't fooling anybody.

    With a history of overpaying the likes of Kevin Brown and Carl Pavano, breaking the bank to keep Jeter doesn't seem like too much to ask.

    If you have it, you might as well spend it.

1 No: Jeter Will Always Be Remembered as a New York Yankee Great

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    No matter where Jeter ends up playing the remainder of his career, he will be remembered as a Yankee great.

    Even if he walks away, it seems unlikely he would have more than two productive years as a full-time shortstop left.

    If he stays, two more decent seasons would end up justifying his deal.

    In many ways, he has already cemented his legacy in Major League Baseball.

    Anything else he does will merely be icing on the cake.

    Even if that icing is worth around $20 million.

1 Yes: Public Backlash Will Be Incredible

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    No matter what happens, there will be reaction to Jeter's fate.

    If he stays in New York, there will be criticism that the Yankees overpaid to keep a mediocre shortstop who is nearing the end of the road.

    If he walks, the Yankees will be criticized for being too cheap to keep a legend.

    No matter what happens at the conclusion of this sage, the New York media will have plenty of material to editorialize.

    Brace yourselves for a tidal wave of criticism in the press and by Yankee fans, one way or another.

Conclusion: Are the Yankees in a No-Win Situation with Derek Jeter?

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    Chalk it up to their history of ridiculous contracts, the cynicism of an arrogant media and the fact that society doesn't enjoy taking a wait-and-see approach.

    There is no question the Yankees aren't going to look good at the end of the messy negotiation process.

    The best case scenario is also the most unlikely one.

    Assuming Jeter ends up re-signing Derek Jeter, he will need at least two years of solid production to justify his salary.

    How much can you really expect from a full-time shortstop who turns 37 next year?

    Ultimately, what happens in the next few weeks and years will be a mere footnote in Jeter's career.

    Too bad there's no room for revisionist history on Page Six.