[editor's note, by Rox Girl] - bumped from the diaries, OhNoKoolAid brings up a very valid point, as JJ's contract posturing forces us to look at all the scenarios to derive what's in the best interest of the team - Rox Girl

One of this site's biggest strengths, outside of its depth of prospect knowledge and recollection, is its members ability to critically analyze situations associated with roster decision making, while attempting to exhaust all possibilities.  While unfortunately, none of it counts in the "real world," it does make for entertaining debate.  So with that in mind, I believe there is a situation worth looking into more than we already have...

Most of us have acknowledged that this is a pivotal off-season in the Rockies' transformation into a contender, with the 40 man roster crunch, critical players in arbitration, and the need to fill the final gaps in the lineup not handled by the farm system.  To this list, we could soon be adding another major item to the agenda: what to do with a "non-extended" Jason Jennings.

If you're like me, you've probably taken it for granted that Jennings would most likely agree to any reasonable extension, and you found it surprising that Jennings would require serious personal debate before re-upping with the Rockies.  What makes this difficult for Colorado is that adding the players Jennings wants may not be possible until the Rockies are certain what Jennings will take off the books for the next few years.  As some have suggested, Jennings may ultimately be determined to test the open market, or just flee from the "stigma" that is Coors (to be saved for another discussion...)  So what are Colorado's options with Jennings?

First, I should make it clear that my first wish is for Jennings to be here for the foreseeable future, and this is by no means a "Trade Jennings" post, but instead a discussion on what the Rockies could recover should they feel forced to move him.   Just some perspective before going further...

Because we don't know the real intentions of Jennings, we are forced to speculate on several scenarios.  One could be that Jennings is using these comments in the media to get the Rockies attention, to show the owners and front office that the core players would like to see a more aggressive off-season.  He might be leaning towards extension, but wants an assurance from the Monforts and Co. that they will make a better effort to service this club properly.  We all might hope that this might be the reality, but in case t isn't, what are the options available for the Rockies?

One could be to just hang on to Jennings through the 2007 season, waiting to see if the team stays competitive through the deadline, dealing him if they are not, or taking there chances in resigning him should they be more successful than this past season.  Besides the obvious benefit of having Jennings in the rotation another year, the Rockies would also be in line for a couple of draft picks should Jennings decline the Rockies request for arbitration.  There are risks involved for both sides.  For Jennings, pitching in a contract year has its dangers, just ask Mark Mulder.  A devastating arm injury would without an extension with the Rockies could result in the loss of  millions in free agency.  For the Rockies, not only do you risk losing Jennings for "nothing," but should he suffer a down or injury plagued year, it could effect the draft compensation should he leave anyways.  For the Rockies to take this route, it would require confidence that they are not only fielding a team they feel will be successful, but possible assurances that Jennings would likely re-sign after the season should they meet his request for a more competitive roster.

The other obvious option is the trade route, and should Jennings not opt for an extension or show signs of agreeing to one, I find this route the more attractive of the two for a few reasons.  First, realize that Jennings would likely be one of the hottest commodities should the Rockies deem him available.  Not only is he young, durable, and healthy, his numbers took a serious turn for the better this season, and while he might not have achieved just media acclaim, you can be sure that general managers around the league did take notice.  With the dearth of solid pitching options available in free agency this year, Jennings might be sold for higher than face value, and considering the Rockies desire for an all-star bat, preferably one that plays center, this could still turn into a good thing.

In my opinion, should Jennings be made available, I would prefer not to trade him for a high salary or soon-to-be high salary player like Vernon Wells.  While he's the most attractive center field name on the market, with Jennings as a trading chip, you could probably target a major league ready prospect, keeping the roster expenses low and allowing some of the money to be used to cover Jennings contract go to arbitration eligible players or niche free agents.  The first teams I would call would be the New York Mets and the Chicago Cubs.  The cubs might be tougher to deal with than New York.  With Pierre out of the picture, it could be Pie's job to lose in Wrigley, and the Cubs might not be so eager to part with him.  If management in Chicago, however, decides to supplement their new manager with veteran players, Pie could become "expendable" if he's blocked by an acquisition.  He represents a cost effective alternative to centerfield with potential to bring a high reward for the cost.

The ideal trade, however, would be for Lastings Milledge from the Mets.  It's unclear if Milledge was actually available for Zito at the deadline, but it's worth looking into with Jennings.  With the media's cry for a better pitching staff in New York, Jennings could be justified by the front office for his youth, prospective price tag, and success in what is deemed a "hostile environment" at Coors.  His durability for a fragile Mets rotation would also be a major plus.  As for Milledge, if Beane did in fact want him, he's probably pretty good, and his numbers bear this out themselves.  He's a more natural centerfielder and could be a Mike Cameron-type at Coors, which, for the years of control the Rockies would have on him, would be a major bargain.  If you wanted to get really creative, add Brad Hawpe to the deal in hopes of getting Aaron Heilman thrown in as well.  Heilman has the numbers to be a very good starter, and could balance the loss of Jennings in the rotation.  Hawpe isn't necessarily expendable, since Baker's BABIP inflated September performance could be a bit flukish, but with Smith and Stewart a step away from the bigs, reinforcements aren't far away.

Straying away from prospects, the next best target would be Rocco Baldelli.  Malakian has pointed out that the Rays might be in the market for pitching, and willing to deal from their outfield excesses, and Jennings would probably be the best big league name offered to them.  What I like about Baldelli is that his numbers not only are improving year after year, and his defense is gold glove caliber, but he has a long term contract already laid out, negotiated by himself, with reasonable bonus clauses and base salaries, and you can see it here courtesy of Cot's Baseball contracts:

http://mlbcontracts.blogspot.com/2005/01/tampa-bay-devil-rays_112131227267025321.html

His best years are ahead of him, and the Rockies can control him under this contract until 2011.  What makes this more attractive is the amount of buyouts and options back loaded on the contract, giving the Rockies an escape if he underperforms and Fowler proves ready to handle the bigs in the next few years.  This might require a one-for-one swap, or even a prospect from our side, but little money is added to the payroll, when you consider what an extension to Jennings would cost.

So here are just a few ideas to get the ball rolling, and these can even be debated into refutation.  Another concern might be who we acquire or rely on to replace Jennings, and I have a few ideas on that, but will let this develop a bit more.