Whom should the Sox pursue this offseason? Review the possibilities and vote.

Now begins the intriguing case of Jason Bay, a man whose contract negotiations with the Red Sox are, in some ways, unprecedented. Players have continued to come and go during the current Red Sox administration. Yet now the Sox are faced, perhaps for the first time, with a potential fight for a player they truly want to keep.

One day after the 2009 World Series concluded, baseball’s offseason officially began yesterday with the first day of the free agency filing process. Bay was one of the players who immediately declared his freedom. Most everyone agrees that Bay and outfielder Matt Holliday (who also filed) are the best positional players available on the market this offseason, and both are obvious fits for a Sox club that has both a gaping hole in left field to go along with a gaping hole in the middle of the lineup.

The questions today are the same questions that have existed throughout Bay’s tenure in Boston, during which Bay has led the Red Sox in home runs and RBI while finishing second in runs scored and OPS.

How much is he worth on the open market?

Will the Red Sox be willing to pay it given the manner in which they have approached free agency during the last seven years?

During the tenure of general manager Theo Epstein, three free-agent pursuits stand out above all others: J.D. Drew, Daisuke Matsuzaka and Mark Teixeira. Beyond that trio, the Red Sox generally have not offered any player more than a four-year deal in the range of $40-$50 million. The Sox have shown a willingness to spend big only when their preferred factors were in complete alignment, and in those cases they were at least willing to blow most everyone out of the water.

In the case of Teixeira, the Sox obviously lost out to the New York Yankees, but that’s not the point. The club still offered him the biggest contract in club history. At the time, Teixeira was a 28-year-old, switch-hitting, two-time Gold Glove winner who could hit for average and power. In terms of long-term investments, he was about as safe it gets. No one should be surprised that this Red Sox administration was willing to go to unprecedented lengths (for them) to secure his talents.

Matsuzaka, meanwhile, came with greater risk given that he had never played in the major leagues, but the other factors were otherwise in alignment. He was 26 when the Red Sox invested $103 million in him over six years. Technically speaking, Matsuzaka is on the Red Sox payroll for an average of $8.67 million per year from 2007-2012, but the $51.11 million posting fee was absolutely part of the cost for him. The reality is that the Matsuzaka deal cost the Red Sox an average of $17.17 million per year.

All of this brings us to Drew, who is easily the most comparable case to Bay given that both are corner outfielders. Following the 2006 season, Drew was precisely the same age (31) that Bay is now. The Red Sox gave him a five-year, $70 million contract that opened eyes through the baseball world and that Epstein still is defending. In late September, Epstein invited discussion on Drew on 98.5 The Sports Hub, pointing out that Drew had "the second-highest OPS" among all American League outfielders, a particularly relevant characterization given who finished the year ranking first.

That would be Bay.

Here’s the other reason the Red Sox valued Drew: defense, an area in which Bay is, on the whole, mediocre, and also one on which the Sox are likely to place undue emphasis (some media types are already taking the bait on this) for the purposes of driving down the price. But then, negotiations are all about leverage. Drew’s ability to play right field at Fenway Park – one of the bigger areas in baseball – prompted Epstein to suggest last winter that Drew had greater value to the Sox than he did to other teams, and whether one agrees with the GM is irrelevant. The important thing to remember is that the Red Sox have certain philosophies and formulas that they believe in, and they have shown a willingness to pay for it when their criteria are met.

With regard to Bay, part of the problem is that the Sox don’t appear to have any better options to replace him, be it through trade or free agency. They don’t have a hitter like him ready in their minor league system. Holliday would cost at least as much or more, and his brief stint in the AL (let alone Boston) left a great deal to be desired. A trade would require further forfeiture of young talent from a Sox system that has hit somewhat of a developmental hole, particularly after a flurry of necessary, in-season trades this year.

The bottom line is that the Red Sox seem backed into a corner here.

While representatives for Bay and the Sox have remained remarkable tight-lipped during negotiations that began last spring, it’s hard to imagine Bay settling for anything less than what the Sox awarded Drew, be it in years (again, five) or dollars ($70 million, an average of $14 million per). The likelihood is that Bay will command closer to $16-$18 million per year given his elite status on the market, which could place his final cost somewhere in the range of $80-$90 million over five years. (In case you’re wondering, that is purely an opinion.)

For what it’s worth, during his major league career as a starter (2004-09), Bay ranks in the top 10 of all major league outfielders in OPS, a statistic on which the Sox have placed great emphasis and in which Bay and Drew have been a virtual dead heat over the last six years. Bay beats Drew handily in games played (892-749), home runs (181-120), runs scored (564-497) and RBI (596-425), though the latter is a statistic, according to Epstein’s same radio interview, that the Sox generally discount entirely. Whether that disclosure is 100 percent fact or merely served as initial posturing for the Bay negotiations remains to be seen, largely because Bay’s representative (Joe Urbon) is not likely to deem his player’s run production irrelevant.

During Bay’s career as a starter, only five outfielders in the game have knocked in more runs: Carlos Lee, Manny Ramirez, Bobby Abreu, Vladimir Guerrero and Adam Dunn, the last of whom is a defensive sinkhole and whose recent free-agent contract (two years, $20 million) badly skews the data. All of the others, in the primes of their careers, earned average annual salaries between $15 million and $20 million.

Regardless, there is more pressure on the Sox to keep in Bay in Boston than there ever has been on them ever before, with possible of exception of Jason Varitek, who filed for free agency for the first time following the 2004 season. Even then, most everyone in baseball knew Varitek’s priority was to remain with the Sox – to the point where he all but spurned other suitors. In the other major free agency filings during the administration of John Henry, Tom Werner, Larry Lucchino and Epstein, the Sox either have happily let aging players depart (Pedro Martinez, Johnny Damon and Derek Lowe, among others), traded them before the fact (Nomar Garciaparra, Manny Ramirez) or reluctantly re-signed them (Mike Lowell).

But Bay? The Red Sox want him and they need him.

We just don’t know if they’re going to pay him.