Alex Rodriguez

In 2008, Derek Jeter posted the lowest full-season OPS (.771) of his career.  That's not a bad number for a 34-year-old shortstop, but it was enough to make some Yankee fans wonder if their captain was on the decline and what might happen when Jeter's contract expired after the 2010 season.  Would Jeter insist on remaining at shortstop?  Would he want a salary close to the $21MM he's set to make in 2010?  And, if Jeter continued to struggle and the Yankees balked at committing so much money to their star, would New York fans have to cope with seeing their beloved Jeter in another team's uniform in 2011?

These questions still remain to some extent a year later, but in the wake of Jeter's excellent .334/.406/.465 performance in 2009 and the Yankees' 27th World Series title, there is a lot less fear in New York that a Jeter extension will turn into an albatross on the club's payroll. 

As per team policy, contract negotiations with Jeter won't begin until after the season, but it's safe to assume that this delay won't be a distraction for either Jeter or the team.  Tyler Kepner of the New York Times predicts "a quick resolution and a new contract that greatly enriches Jeter while preserving his spotless reputation."  There won't be much, if any, drama in the negotiations since Kepner notes that Jeter recognizes the value of his clean image as a franchise hero, and the Yankees similarly want to keep their "dependable, well-spoken, maintenance-free front man."

Kepner thinks the 10-year, $275MM contract that Alex Rodriguez signed with New York after the 2007 season may serve as a benchmark for Jeter's next deal.  Given how much the economics of both baseball and the world have changed just in two years' time, it would be surprising to see even the Yankees commit that much cash to a player who will be 36 in June, no matter how big of a franchise icon he may be.  Also, as Kepner notes, Jeter has managed to avoid the scrutiny that comes with big-money contract negotiations ever since signing his current deal back in 2001.  It's unlikely that Jeter would want to change that as he enters the twilight years of his career and the chances increase that he'll have more seasons like his 2008 campaign. 

Something in the neighborhood of a six-year contract that pays Jeter around $22MM per year (a nod to his uniform number) might be a total more to the liking of both parties.  Jeter gets a slight raise from his previous contract, is locked up until he's 42 years old, and is amply rewarded for his contributions to the team while still leaving the Yankees with a bit of flexibility to sign other players (like, for example, fellow Yankee legend Mariano Rivera, whose deal is also up after 2010).

There could also be a mutual option year or two tacked onto the end of the deal in case the 42-year-old Jeter still wants to play and/or he has a chance of breaking Pete Rose's hit record.  Kepner raised the possibility that Jeter may ask for incentive clauses for passing various hit plateaus, similar to how A-Rod's contract provides him with a $6MM bonus whenever (or if-ever) he passes the career home run totals of Willie Mays, Babe Ruth, Hank Aaron and then tying and breaking Barry Bonds' all-time record.  Jeter is just 253 hits away from 3,000, but, as Rose himself said to Sports Illustrated's Joe Posnanski, “You tell Derek that the first 3,000 are easy.”

Since we can assume that 99 percent of Yankee fans want to see Jeter retire in the Bronx, what do you think would be an ideal contract to keep the captain in the fold until the end of his career?