New York Yankees: The Derek Jeter Dilemna

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New York Yankees: The Derek Jeter Dilemna
Stephen Dunn/Getty Images
This quagmire is dominating the offseason.

Picture a franchise player who was once considered one of the best players in baseball.  Fans watched him grow from an ambitious kid to a superstar, to now what could be the twilight of his career.  This is the case of Derek Jeter and the New York Yankees.

Ten years ago, Mr. Jeter signed a 10-year deal worth $189 million.  He earned every penny of that contract as he perpetually hit over .300, played stellar (and underrated) defense and won more championships than any other player in baseball except for his other core four teammates.

However, last year was his walk year, and Mr. Jeter had undoubtedly the worst season of his career.  He hit a paltry .270, and despite winning the Gold Glove, seemed a step slower in the field.  2010 was most definitely the worst season of his career.  Also, he turns 37 next June and it could be a recipe for disaster.

Any 36-year-old shortstop would have no business demanding a four-year deal.  Like catchers and pitchers, they have a short shelf life as they rely on their speed and athleticism to thrive in the field.  Couple that with naturally slowing bat speed—and a four-year deal usually does not work well for the team that signs the player.  Only two shortstops in recent memory were still playing at a high level into their 40s: future Hall of Famers Barry Larkin and Omar Vizquel.

That being said, Jeter’s agent, Casey Close, is pushing for a four or five-year deal.  Any other 36-year-old shortstop would never receive a deal of four years, and would likely get two at most.  The Yankees seem to be targeting a three-year deal.

So now, Yankees GM Brian Cashman is now stuck between a rock and a hard place. He must find a way to sign Jeter to a new deal because he is still the best shortstop available, and he is still Derek Jeter.  Jeter’s place in New York is so solidified that a failure to re-sign him would vilify Mr. Cashman for the rest of his tenure in the Bronx.

Both sides should agree to a three-year deal worth $45 million.  Jeter’s production was way down last year, but it could also be an anomaly, where he reverts back to form in 2011.  The deal would also give him a chance to reach 3,000 hits, a feat no Yankee has achieved, as well as the possibility of getting close to Pete Rose’s all-time hits record.   Most importantly, it keeps Derek in the Bronx for the rest of his career—a rarity in this business.

While newspapers, websites and ESPN seem to be making a big deal of the contract negotiations, and Yankees officials calling the negotiations a “messy” process, a deal will most definitely be done.  Expect Jete’ in pinstripes on opening day 2011.

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