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The Derek Jeter Situation

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When the Major League Baseball Players' Association sent out a press release moments after the end of the World Series, it listed the names of 142 players that would be free agents this off-season. While Cliff Lee, Carl Crawford and Jayson Werth are the big names that could have a big impact on whichever teams they wind up signing with, its the Derek Jeter case that might be the most interesting of all.

Of course, Jeter isn't seen in the same light as most of these other big name free agents, as there's probably a 99% chance that he stays in New York and continues to hold his spot as one of the greatest Yankees of all time. The problem is, the Yankees are probably going to have to vastly overpay him - from a baseball perspective - to do so, whether that comes in dollars, years, or both. Yes, there is probably a value that can be associated with Jeter above and beyond his baseball talents, which FanGraphs valued this year at $9.8M, which certainly isn't bad. But Jeter is 36 years old, and even the most optimistic fans of the Yankees franchise player have to feel that his career is heading into its decline phase.

From a baseball standpoint, Jeter's case isn't unusual. In most cases, a player in Jeter's scenario would likely be looking at a short-term deal of one- or two-years, close to the value he was worth in 2010. But it seems apparent that a one-year deal for $10M, or perhaps a two-year $18M deal won't be enough to get Jeter to sign on the dotted line. With the man who plays third base in New York, Alex Rodriguez, set to earn an average of $27.5M yearly until 2017, it would seem Jeter might feel he's more in line for a deal more similar to that. As Sports Illustrated's Jon Heyman pointed out today, that would mean Jeter is seeking a six-year deal, to end at the some point, and probably closer to $20M than $10M.

For a team like the Yankees though, it must be the years that matter more than the dollars. Will it bankrupt the team if they're paying Jeter $18M a year rather than $10M? Probably not. It's keeping him in the batting lineup that could have the most impact.

Keeping Jeter around at shortstop for the next two years or so isn't too risky. As much as they may try to negotiate in public by acting like Eduardo Nunez is going to be the heir to Jeter, I can't believe that a team with a front office that smart believes that to be the case. Nunez may profile as an off-the-bench utility player down the road, but few scouting experts out there would tell you that Nunez can be a successful everyday player in the tough AL East. With no one else that close in the farm system, and the difficulty of signing or trading for high-level shortstops, the Yankees look to have no real options besides Jeter anytime soon. Even if the cost is $20M per season, the opportunity cost for the high-budget Yankees to play Jeter at the premium position is minimal.

The bigger challenge arises if Jeter is seeking more in terms of years - which reports today seem to hint at. Jeter's range at shortstop is declining, and his days there seem to be numbered. The Yankees may be able to get away with playing him there for the next couple of years, but betting on any more than that seems like a mistake. When Jeter's days at shortstop are done, where does he go? The other spots in the infield are all locked up by stars that don't look likely to be going anywhere - Alex Rodriguez, Robinson Cano and Mark Teixeira. Some speculate that the Yankees may try to move him to left field, but is it really reasonable to expect a player in his late thirties to learn an entirely new position, and do well at it?

That essentially leaves the DH spot, though at least as planned now, that spot may have to be given to Yankees mega-prospect Jesus Montero, who most scouts believe will not be able to stick at his current position, catcher. Many have speculated that the Yankees will need to trade Montero this off-season, to a team that can use him at first-base (whereas the Yankees have that spot blocked by Teixeira). After all, the Yankees were all set to deal him to the Seattle Mariners in exchange for Cliff Lee in July, before the Rangers jumped in and topped that offer with a package based around Justin Smoak. Still, even if the DH spot is vacant, is Jeter really a solution there? While most teams will play one of there top offensive players as the DH, it seems that the likelihood of Jeter holding up to that standard and being a quality AL East DH are slim to none.

All of this adds up to an incredibly interesting negotiation ahead. When the Yankees offer a two-year deal and Jeter asks for six, will the two sides be able to work something out in between? Committing four years to Jeter as a shortstop is risky, but for a team with the Yankees budget, it isn't quite as dangerous as it would be for a small-market team.

But what if there's another team that jumps in? Maybe a team out there has a spot for Jeter at shortstop now, and figures to have other infield openings down the road. Would they be willing to make a six-year pact with the Yankee legend? Or would doing so for any other team, besides the Yankees, not only be an incredible risk, but also nowhere near worth the money it would cost to get it done? We've heard the Detroit Tigers name come up, and it's certainly likely that we'll at least hear discussion of other teams.

If for no other reason than to drive the price of salary and years up, it may be wise for a large number of teams to get involved in the bidding. As much as Jeter's legacy means to the Yankees, his presence in their lineup as he nears his 40s could present a very tough matter to handle.

So while Derek Jeter is almost certain to end up in the exact same spot on Opening Day 2011 as he's been for over a decade, his signing this off-season may wind up having more impact than any other contract handed out this winter.