Derek Jeter has embodied what it means to put on the Yankees pinstripes and be the captain of the most captivating, hated and loved team in all of professional sports.  Despite all of his contributions—nearly 3,000 hits, nearly 250 home runs, countless 200 hit-100 run seasons—emotion needs to be taken out of the negotiations. 

The truth is that eventually the New York Yankees will need to move away from the “core four” who all have legitimate shots to be enshrined in Cooperstown for their winning pedigree, and giving Jeter a deal that doesn’t affect their long term financial situation would really help the team win. 

If they are able to give Jeter a fair market deal of which one anonymous MLB executive is between $7 and $8 million per year at three years, then it would shore up some money to get Cliff Lee.

The negotiations will be slowed by the fact that Jeter wants to be compensated like his neighbor to the left, Alex Rodriguez, who will earn upwards of $30 million even at age 42.  The Yankees and everyone else around baseball will admit that Rodriguez’s contract is a horrible one and he may be broken down and a full-time DH by then, but Jeter feels that everything he has done for the Yankees entitles him to have a similar deal.

The reality is that Jeter will be 37 this summer and has lost range defensively and only hit .270 in 2010.  The Yankees and Derek Jeter can’t just walk away from a deal but they need to both concede some in negotiations and have perspective that Jeter can still be a solid contributor but he is about the seventh best player on the team at this point in his career. 

If I am Brian Cashman, the deal that I lay out is two years for $30 million with a team option for a third year at $17 million.  This will give Jeter a solid base salary but will not hamper the Yankees long term financial future. 

In this deal, I would also include that if he retires a Yankee and plays with them for the duration of his career, he can work five years in the organization in a role similar to Reggie Jackson’s and then upon the completion of those five years, he acquires 2 percent of the ownership of the team.

The Yankees need to remember ultimately they will have to move on from Jeter and the rest of the “core four” eventually and by giving him this deal it will allow Jeter to play but still be motivated to achieve and will also give him money towards the end of his career. If Jeter accepts this deal, he will be a Yankee for life and go down with the likes of Mickey Mantle, Joe Dimaggio and Lou Gehrig as Hall of Fame Yankees.

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