By R.J. Anderson //

Derek Jeter is a free agent by name only. The Yankees’ only conundrum in re-signing their captain will be similar to the ones the Bombers faced with Andy Pettitte last offseason: how long and for how much?

Those questions are not easy to answer in this case, because Jeter’s marketing power and brand are unrivaled. The Yankees’ own brand would not suffer from losing Jeter – they were popular before him too, you know – but they have no reason to pass on him (despite diminishing skills) because a sunk cost is no big deal to New York.

Jeter’s 2010 season represents a massive disappointment. Fresh off a season in which hit .334/.406/.465 with 18 home runs, Jeter failed to come near those numbers. His batting average slipped under .300 (to .270) for the first time since 2004. His on-base percentage fell below .350 (.340) for the first time in his career – the same can be said of his slugging percentage ending at less than .400. Jeter still managed 10 home runs and 18 stolen bases, but his mediocre stats and slap-hitting ways might represent the future more than Yankees fans would like to believe.

In June, Jeter will turn 37. No shortstop (defined by having played at least 50% of their games at the position along with 300 plate appearances) aged at least 37 has ever hit more than nine home runs in a season. Since 1970, only 20 shortstops met that qualification after turning 37, with the highest batting average being .295, the highest on-base percentage being .367, and the highest slugging percentage being .419. Over the last three seasons, Jeter’s line: .301/.369/.414. Meanwhile, only two of those players finished with an OPS above the league’s average.

In other words, Jeter’s not likely to get much better than he’s played lately as he ages. The crowd perception is that Jeter will get a deal worth three years at roughly $15 million per year. Even though three years does not seem like a long time, one has to wonder if Jeter’s increasing immobility at shortstop along with the presence of prospect Eduardo Nunez will result in the Yankees moving Jeter to the outfield or full-time DH before the contract expires. Moving him becomes a definite if the Yankees foolishly give in to Jeter’s supposed desire for six years. Consider the idea admirable – in the sense that Jeter loves to play and really wants to test the limits of his icon boundaries – but also insane.

As for your fantasy docket, one would expect him to be undervalued entering next season, and there’s something possibility for a bit of positive regression after such a huge year-over-year drop. Still, in most leagues Jeter’s name value will inflate his bidding price beyond a reasonable range.

Tread softly and do not be afraid to let him go. Unlike the Yankees, you have a choice.

For more on Derek Jeter and other free agents, check out Bloomberg Sports’ Fantasy Tools.