New York Yankees shortstop Derek Jeter enters the 2009 season 465 base hits shy of 3,000. It is safe to say that Jeter, the Captain and face of the franchise during the Dynasty years, and his loyal fans expect him to reach the 3,000-hit club while wearing Pinstripes.

The question, though, is should, and will, the Yankees give him the chance to do so in the Bronx?

It goes without saying. Jeter is one of the best offensive shortstops of all time, a no-doubt-about-it future Hall of Famer. However, his current contract--which is absolutely massive, by the way--expires at the end of 2010. At that point, the New York front office will be faced with an extremely difficult decision, especially if the fan favorite and face of the organization, as expected, continues to decline with age.

Right now, Jeter is already showing signs of a major drop-off. For starters, he can no longer play shortstop adequately at the major league level. Especially for a club that expects to compete for championships. Sorry, Captain lovers, but facts are facts. Although the former Gold Glover has sure hands, a playable arm and a reputation for being a wizard in the field, his range is seriously limited. According to all of the objective advanced defensive metrics, in fact, he is one of the least effective defenders at the position in the game; he has posted negative UZR totals (including -15.5 in 2005 and -16.5 in 2007) in five straight seasons. For those who may not be aware, the most important factor to consider when judging defensive value is not the number of errors a player is responsible for, but rather the number of plays that he makes; this is where the problems with his defense lie. Obviously, a player cannot record an error on a ball that he cannot reach.

Jeter, as cool as he looks with his jump throws from the hole, simply lets too many balls to his left and right side that should be converted into outs go in for base hits, thus inflating the ERAs of every New York pitcher. Objectively, he has been hurting the Yankees, whose terrible defensive efficiency ratings as of late are not just a coincidence, while playing such an important up-the-middle position so poorly. The casual fan has a mental model of Jeter making exceptional defensive plays burned into their brain, from his in-the-stands grab against the Boston Red Sox to the infamous ball flip to catcher Jorge Posada to save a huge playoff game against the Oakland A's.

Mental models, however, are driven by biased, subjective thought processes, one or a few isolated images. Objective data, on the other hand, simply does not lie, nor does it give bonus points to certain players for perceived likeability or star appeal. Essentially, there is absolutely no conspiracy against Jeter because he used to date Jessica Biel and those "basement-dwelling stat heads" who frequently deride his defense only can do so in their dreams.

Statistical analysts do not call him Past-A-Diving Jeter for their own amusement.

Also, while advanced defensive statistics have some flaws, a number of scouts agree with the conclusions drawn in the statistical community. Many scouts have also documented how Jeter has difficulty getting to balls a few steps to his left or right; it would be difficult for a trained talent evaluator, or anyone looking for it on the YES! Network, not to notice.

Defensive deficiencies aside, the soon-to-35-year-old middle infielder has been a productive hitter since winning the Rookie of the Year and helping the Yankees to the World Series all the way back in 1996. He has put up a career line of .316/.387/.458 with a 120 OPS+ in 8,025 at-bats over 14 seasons. Not too many shortstops can boast that kind of an offensive resume, and, though he is a perhaps a bit overrated, there is no denying what he has accomplished with a bat in his hands--especially for a shortstop, even one who is so limited defensively. Despite his shortcomings with the glove, he has also been quite valuable overall; he has produced the following value wins totals (accounting for defense, offense and positional factors) since 2004, respectively: 5.0, 4.5, 6.4, 3.7, 3.7. While he has been on the wrong side of the dollars earned/dollars made chart, for the most part, he has been an excellent player who should not be faulted for accepting such an enormous amount of money from the Steinbrenner fortune.

Jeter, with his 6.4-win campaign, was, in fact, a legitimate M.V.P. candidate back in 2006, which was not all that long ago. He hit an outstanding .343/.417/.483, producing the second-best OPS+ total, 132, of his stellar career in the Bronx. With that said, his key offensive numbers have been headed in the wrong direction since that monster performance in '06.

2006: OPS+ 132, BB% 10.1, ISO .140, Line Drive % 22.3, SLG .483
2007: OPS+ 121, BB%, 8.1, ISO, .130 Line Drive % 19.9, SLG .452
2008: OPS+ 102, BB%, 8.0, ISO, .107 Line Drive % 17.9, SLG .408

Jeter was nagged by injuries in '08, and should rebound a bit at the plate this season. Still, counting on him to replicate his '06 hitting exploits seems like a trap. He will turn 35 in the spring, meaning that he is clearly past the peak stages of his career. Also, there is no telling how much longer the Yankees are going be willing to live with his poor play at shortstop; the Yanks ranked 25th in converting batted balls hit into play into outs this past season, one of the most overlooked aspects of their failure to reach the postseason for the first time since Jeter took over at short as a rookie. Even mainstream writers are starting to notice, as his poor range was on show for the world to see in Team USA's thrilling come-from-behind win in the World Baseball Classic on Tuesday night.

This is the root of the problem, of course, and brings us back to the question above. Where should the Yanks move Jeter when the day comes where his defensive lapses are even more obvious than they are now? The corners--as any baseball fan has heard--are locked up for most of the next decade, with two of the most productive offensive players in the league. As he declines, there is no way that Jeter will provide enough pop to man either position, anyway, let alone move Alex Rodriguez or Mark Teixeira off their respective positions. Essentially, as soon as he moves out of the middle infield, which is painful, but inevitable, his ultimate overall value will suffer greatly. True, he does go back well on fly balls and is a better athlete than his range will lead one to believe, so perhaps he could move to an outfield spot; however, many analysts and scouts do not think this will ever happen. Regardless of where he moves, though, his bat will no longer play as well as it does currently.

Jeter will be entering his 37-year-old season in 2011, the first year of any new contract or extension. Thus, odds are his skill set will be worse at that point. Again, he is past his peak. Teams need to leave sentiment out of roster decisions, riding a star player's peak and then letting him become someone else's financial burden when all signs point to a performance slippage.

The Yankees, as difficult as it will be, and as much short-term heat as they will take from the Bill Maddens and Ian O'Connors of the world, would be wise to follow that mindset, parting ways with the Captain unless he is willing to take a massive pay cut and shift to a utility role for the '11 season. This may sound crazy to some, but it is important not to be blinded Jeter of yesteryear, who was so instrumental in the Yanks' brilliant run of dominance at the end of the last decade. He is not, and will not be then, the same player. Jeter is a class act who does provide intangible qualities that cannot be quantified, but how much will the club be willing to spend for those attributes?

New York must think about its future when the time comes, and, while they will feel the wrath from a likely-agitated fan base if they make the right baseball choice, adding a more capable replacement at shortstop when the time comes will ultimately better prepare the club to add to the historic number of championship banners. Yanks fans are loyal with their guys--Paul O'Neill, Bernie Williams--and will always hold a place in their heart for number 2. When it comes down to it, though, most Bomber lovers care more about winning, which will cure all, than individual accomplishments or players.

If Jeter decides against remaining with the Yanks in a more limited role to instead pursue a chance to play everyday--assuming he does not post 200-plus hits to reach 3,000 before the end of his current contract--then so be it if he reaches the milestone with another team. It would indeed be sad if he does not record that special base hit with the only team that he has ever known, his favorite team growing up as a kid in New Jersey/Michigan, but business is business. Winning is all that matters. Or at least should be.

The Houston Astros' on-field product suffered tremendously when management let Craig Biggio chase the 3,000 club during the '06 and '07 seasons. Drayton McClane, the Astros' owner, was more than happy to plan out a Biggio Farewell Tour, which hurt his team's chances of competing; as underrated as he once was, the veteran second baseman was below replacement-level his final go-round in the show. It was classy to let the one-time Killer B go out on his own terms, but the consequences of that love fest and misguided short-term thought process still affect the Houston organization, extremely thin on talent, today.

Obviously, the Yankees will have two more years before they are forced to make the decision. There is no rush here. Who knows? Perhaps Jeter will offer to take less money to remain a lifelong Yankee (although he is viewed as a team-first guy, do not take that to the bank), agreeing to a Tim Wakefield-like and affordable contract to remain a utility man in New York until he retires. This way, he will definitely reach the 3,000-club with the Yanks. Brian Cashman (if he remains general manager long enough to weigh in) and ownership must start thinking about it now, though, because odds are his defense will slip to an unplayable level before then. The day when Jeter is no longer the regular shortstop at New Yankee stadium will creep up soon enough, count on that.

Regardless of what happens, this debate will surely rage on for the next two years. Eat your heart out, wFAN.

This piece was originally posted at http://mvn.com/aroundthemajors/2009/03/yanks-will-have-a-tough-decision-to-make-with-jeter.html