I'll throw out a few names for you; Jason Bay, Dustin Pedroia, Jonathan Papelbon, Kevin Youkilis, Jon Lester.
While each of these players is currently "under team control" for next season and in most cases beyond, each could pen to paper on a new contract this offseason. At the same time, each enters their respective negotiations with their teams under slightly different circumstances.
Arbitration Eligible: Jonathan Papelbon, Kevin Youkilis
Arbitration has a nasty stigma to it these days, and to some degree that stigma is deserved. For many players, arbitration is seen as half threat ("I'll see you in arbitration") and half slap in the face ("Oh, you don't think I am worth that?").
In the case of two of the most valuable current Red Sox on the roster, Kevin Youkilis and Jonathan Papelbon, arbitration in 2009 is a very real reality. To this point in Theo Epstein's reign as the head of baseball operations in Boston, no negotiation has reached the control of third party.
Kevin Youkilis avoided arbitration near the deadline before this past season agreeing to a one year, $3 million dollar deal. Given Youk's 2008 season, All-Star appearance, Hank Aaron Award, and likely high finish in the AL MVP balloting, I expect Youk to play his cards for the long term payday. "It's either sign me up, or let me go to arbitration and expect me to hit free agency." At the same time, I fully expect the Red Sox to set a market value for a 30 year old first baseman/third baseman coming off a career year and place an offer sheet in front of him. I fully expect a three or four year deal at an average of $8 million to $10 million per to be agreed to heading into next season.
Jonathan Papelbon on the other hand presents a curious decision. He's the best at his position in baseball. Francisco Rodriguez will set the market for closers this offseason and likely sign a five year deal between $60 million and $75 million dollars; a far cry from the $750k that Papelbon raked in this season. Given the height of the closer dollar, it is hard to believe that the Red Sox and Papelbon won't go year to year negotiating annual contracts without reaching arbitration. At the same time, both sides may in fact benefit from a three or four year deal at the $5 million to $8 million escalating contract. Although K-Rod's record $10 million dollar arbitration win last season set's a higher mark and I believe Papelbon to be the better player, I don't think that an arbiter will set the bar that high based on current salary and service time.
Non-arbitration Eligible: Jon Lester, Dustin Pedroia
Both Jon Lester and Dustin Pedroia had breakout seasons in 2008 blossoming into perennial post-season award contenders for the next half decade. Given that they are set to renew their current contracts under team control next season, they are both eligible candidates for the "Nomar Treatment". The logic here is give them more money than they are set to get over the next two or three years and get those contracts under market value in years three, four, and/or five.
In Dustin Pedroia's case, I expect both sides to pursue such a negotiation. It only makes sense given what he currently means to this team and the relative dearth of MVP caliber second baseman around.
While I think Lester and the team will have similar conversations this offseason regarding a long term deal, I expect the Red Sox to give him a one year contract like they did Pedroia coming into this season near the $500k level with the likelihood that negotiations on a longer term deal are one more year away.
Free Agents After 2009 Season: Jason Bay
Jason Bay came to the Red Sox with one year left on his current contract set to make $7.5 million in 2009. I've always been of the mindset that Jason Bay wasn't just the "best the Red Sox could get to replace Manny Ramirez at the deadline". I do believe there was longer term thought in mind and that Theo Epstein has Jason Bay in his plans in Boston for 2009 and beyond. I think tearing up the $7.5 million dollar contract and offering a three or four year deal at $12 million per would suit both parties this offseason and for the foreseeable future.
Even with these "raises" to internal candidates, the Red Sox will likely still have money to be players in the markets for Mark Teixeira and/or any starting pitcher that they think may be a fit this hot stove season.
Of the five players above (Youkilis, Papelbon, Pedroia, Lester, Bay), who would you most like to see the Red Sox lock in long term contracts with this offseason?