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

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Derek Jeter: Is New Contract Biggest No-Win Deal for Yankees in Sports History?
Al Bello/Getty Images

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.

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