Jason Bay admits that he had no idea what to expect from his first time in a free-agent walk year. Now in the final season of a four-year, $18.25 million deal he signed while with the Pirates, he was curious whether he might start viewing his performance through the lens of dollars and cents rather than the state of his team. He wondered whether slumps might be more challenging, whether the element of the unknown would affect his on-field performance.

As has been the case with so many other uncertainties in his time with the Sox, Bay resolved those questions to his satisfaction. Because he is on a team where winning is not just an expectation but a mandate, it became easy for him to set aside those sorts of personal considerations.

“I have actually been pleasantly surprised the entire year,” said Bay. “I will be the first to admit it, I’ve said it before, I didn’t really know how I would react. Would it be the same or would it be different, being in my first contract year, so to speak.

“To be honest with you, when things were going well I didn’t think I was going to break the bank and when things got real bad I wasn’t thinking I’ve ruined my season by any means. I am pretty good at taking things for what it is everyday and I never, even at this point, I am not thinking with every RBI I get I am adding an extra X amount . . . I don’t buy into that stuff.”

Bay will admit that his situation might have been helped by the fact that he got off to such a strong start this year. Through the first six weeks of the season, he was a middle-of-the-order wrecking ball, hitting .301 with a .433 OBP, .657 slugging mark and 1.090 OPS fueled by 13 homers and 44 RBIs in his first 41 games.

He recognized at the time that such numbers were unsustainable — indeed, he would often caution reporters, half in jest, that he was unlikely to drive in 180 runs — but the performance created the framework for a year when he could simply play. That proved valuable when he did hit an inevitable slump, particularly when Bay’s performance sagged for roughly five weeks this season, as he hit .165 with a .581 OPS, one homer and five runs batted in during a 31-game stretch that ran from late-June through the end of July.

Bay has since emerged from that funk. Starting on Aug. 5, he is hitting .297/.393/.642 with an A.L.-leading 16 homers and 42 RBIs in 47 games. Once again, he is performing at an elite level, and so it is increasingly clear that his mid-year dip will not impact the free-agent market for his services come this offseason.

Multiple industry sources expect that bidding for Bay – who is making $7.5 million this year – will reach at least four years at $14-15 million per year this offseason should the outfielder seek to maximize his worth on the open market. Indeed, some have suggested that he could exceed those estimates, both in years and dollars. Certainly, it could help the slugger’s cause that the number of interested teams is expected to be significant.

The Red Sox have already said, at the time that they tabled negotiations just after the All-Star break, that they expect to discuss an extension with Bay following the season, and so a return seems a legitimate possibility, especially given Bay’s often-stated enthusiasm for playing in Boston and his desire to return. Should he test the waters, however, a look at some teams that will have money coming off the books and a potential need for an outfielder who can serve as an impact bat reveals a potentially robust market:

Angels: Vladimir Guerrero ($15 million salary in ’09), Bobby Abreu ($5m), John Lackey ($10m), Kelvim Escobar ($10m) and Chone Figgins ($5.775) will all be coming off the books. If either Abreu or Guerrero departs, the team would have a need to add an impact bat to the lineup.

Cardinals: If Matt Holliday departs via free agency, St. Louis will almost surely seek a middle-of-the-order replacement to complement Albert Pujols. The team also has Troy Glaus’ $12 million coming off the books.

Giants: Free-agents-to-be Randy Winn ($9.25 million), Randy Johnson ($8 million) and Benji Molina ($6 million) could all be moving on. The team could clearly use an outfield upgrade to its offense, after suffering through Winn’s .674 OPS and Fred Lewis’ .743 mark.

Mariners: Adrian Beltre ($13.4 million), Jarrod Washburn ($10.3 million), Miguel Batista ($9.5 million) and Erik Bedard ($7.75 million) are all free agents after this year. The Mariners will likely want to earmark a significant amount of money for Felix Hernandez, and the team has seemed more likely to commit to building through its farm system than free agency, but given that the M’s have exceeded .500 this year, they might look at their brutal left-field production (far and away the worst in the A.L.) and see the potential for a significant upgrade to vault them into contention.

Mets: With Billy Wagner ($10 million) out the door and Carlos Delgado ($12 million) likely close behind him, the Mets have a need for a bat and some money to spend. Bay has demonstrated that he is capable of handling life in a big market, no small consideration to either of the New York teams as they look to fill needs, and there is no question that New York will be looking for a middle-of-the-order hitter.

White Sox: G.M. Kenny Williams recently told reporters, “I don’t like what I see on the free-agent market, and what I do like, it’s going to cost you a No. 1 [draft pick].” It’s not clear which category Bay falls in.

Still, even after the acquisition of Alex Rios, the departure of Jim Thome ($13 million salary in ’09) and Jose Contreras ($10 million) during this season, along with the possible departure of Jermaine Dye this winter ($11.5 million) could leave the ChiSox in a position to invest. Bay doesn’t necessarily fit the mold of the young, athletic players whom Williams has sought recently, and Chicago is somewhat right-handed dominant in its lineup, but Bay’s potential to produce in U.S. Cellular Park is significant, and Williams is nothing if not aggressive.

Yankees: With Johnny Damon ($13 million), Hideki Matsui ($13 million) and Xavier Nady ($6.5 million) all eligible for free agency this winter, the Yankees have more than $30 million in outfield/D.H. payroll that will be peeled away this offseason. Even if New York is committed to keeping a spot for top outfield prospect Austin Jackson, New York could sign Bay and, when the time comes, dump Melky Cabrera to make room for its potential centerfielder of the future. Resources, certainly, aren’t the issue for the potential signing of Bay, who does have the added value of a demonstrated ability to succeed while playing in the A.L. East.

Had Jason Varitek (and agent Scott Boras) accepted salary arbitration, and with it a guarantee of more than $10 million for the 2009 season, none of this would have been an issue. But the Red Sox captain (and his agent) declined the offer, and the market for his services has been akin to a desert without an oasis.

There might have been teams interested in Varitek, well aware of his reputation as a masterful handler of a pitching staff, and optimistic that his dismal offensive season (.220/.313/.359/.672) represented at least something of an aberration, even for a 36-year-old catcher. His down-year offensively came in a season when he struggled to deal with a divorce and was also crushed by illness on a couple of occasions, creating some reason for teams to assume that, even if he had entered a period when career decline is likely, the 2008 campaign did not accurately represent his talents.

But when the Red Sox made their offer of arbitration at the beginning of December, the interest in Varitek–a Type A free agent whom a team would have to sacrifice a top draft pick to sign–withered. Teams that might have considered signing him to a short-term deal that minimized risk reversed course.

Tigers President/CEO/GM Dave Dombrowski said as much when his team acquired catcher Gerald Laird from the Rangers. He was not alone in that assessment.

“If we sign him and give up a draft pick,” one N.L. executive said last month, “it would have to be over my dead body.”

The Sox, who would not have to give up a pick to re-sign their Captain, have not closed the door to Varitek’s return. Last week, General Manager Theo Epstein said that the team had ruled nothing out, and had ruled nothing in.

“Jason is still out there,” Epstein said. “As I said at the beginning of the offseason, he’s been a really important guy here to this organization and by no means have we shut the door on him. There’s still some unfinished business there. And also, in the pursuit of a younger catcher.”

But what happens if the Sox acquire another catcher, decide that they do not want to sign Varitek, and other teams remain uninterested in signing him due to the cost of draft-pick compensation? In that scenario, would Varitek be condemned to inactivity by the absence of a market for his services?

Based on conversations with major league officials, the possibility certainly exists. So it is fair to wonder whether Varitek might escape from his predicament, and move into a position where he could sign with a club without requiring a new team to give up a draft pick. According to MLB rules, there are some scenarios that would permit that outcome.

No. 1 — Wait till June

As a Type A free-agent, Varitek would require draft-pick compensation from any club that chose to sign him to a major-league contract before the amateur draft in June. Once the draft takes place, however, a signing club would not have to give the Sox a draft pick as compensation for the catcher.

No. 2 — Red Sox good will

Hypothetically, the Red Sox could decide to waive their right to draft-pick compensation. For obvious reasons, no team has ever done so, nor would any team ever be likely to do so. Why give up a chance to get a free draft pick?

No. 3 — Sign and trade

Varitek could agree to an NBA-style sign-and-trade agreement with the Sox. A club that was reluctant to part with a first-round draft pick to sign Varitek to a free agent could instead agree that, if the Sox signed him for a contract that it found palatable, they would trade a player or prospect of some value (but less than the value of a draft pick) for him. Though Varitek has full no-trade protection with the Sox, he would likely waive that right in order to secure a job if one did not await him in Boston.

Still, that possibility seems at least somewhat limited, since the Sox would have little incentive to abandon the possibility that Varitek would yield a first-round draft pick. While it might seem difficult to imagine a team signing Varitek and giving up a pick now, what happens if a contender’s starting catcher gets injured in spring training? If that occurs, then the Sox might still get a draft pick that could yield a blue-chip prospect.

No. 4: Minor-league contract

In theory, another possibility might exist. If a Type A free-agent signs a minor-league contract, it would be up to the MLB Commissioner’s Office to determine whether he did so out of necessity (no real major-league offers from any team, presumably including the Sox) or to circumvent the compensation requirement. If the latter, then the Commissioner’s Office could award compensation.

In making a determination about the legitimacy of a minor-league deal with major-league terms–for instance, a deal that would give Varitek a minor-league salary but would guarantee him, say, $3 million if he made the major-league roster–MLB would examine:

–What the contract looks like;
–Whether the player had any offers for a major-league contract;
–When the player is called up.

For example, if a player signed a minor-league contract with major-league terms, the major-league terms called for a $1 million bonus upon being promoted to the major leagues and a $3 million salary, and the player was put on the 40-man roster during spring training, that would be scrutinized with immense skepticism by MLB officials. The Commissioner’s Office and teams would clearly frown upon circumvention, since there’s no reason, in theory, why a Type A free agent like Mark Teixeira couldn’t try to dodge draft-pick compensation by signing a minor-league contract that became an eight-year, $180 million deal if he made the major league team in spring training.

The idea of circumventing draft-pick compensation was a topic of conversation in big-league circles in the early days of free agency. As one executive put it, in the 1970s and 1980s, officials tried to figure out what the rules meant by looking for the loopholes to exploit. But only one attempt at circumvention of draft-pick compensation was believed to have been made, and that was in 1988. At that time, an arbitrator ruled that MLB could void such a deal, and no other attempts to circumvent have been made in more than 20 years.

All the same, this offseason is raising questions about the viability of the current system for draft-pick compensation for both players and teams. On the team side, with the Yankees having signed three Type A free agents who were offered salary arbitration (Mark Teixeira from the Angels, CC Sabathia from the Brewers, A.J. Burnett from the Blue Jays), both Milwaukee (which got the Yankees’ second-round pick) and Toronto (which received New York’s third-round pick) drew the short straws. Milwaukee could have been forgiven for being particularly frustrated, since the Brewers traded for Sabathia this summer in part because they expected to get another team’s first-round pick. (One executive noted that a second rounder has roughly a 10 percent chance of making it to the majors.)

On the player side, the offer of arbitration to Type A free agents has undermined the markets for some players. Interest in players like Varitek, shortstop Orlando Cabrera and reliever Juan Cruz has been minimal due to the requirement that clubs would have to give a draft pick to sign them.

The issue–and several others associated with flaws in the free-agent draft-pick compensation system–are almost sure to be visited in the negotiations of the next Collective Bargaining Agreement. Could the draft-pick compensation system be abolished, thereby allowing MLB to create fixed slotting for the amateur draft? That is an issue for another day.

For now, however, the fact of the matter is that players like Varitek and Cabrera who declined salary arbitration and face scant interest are likely kicking themselves, wondering why on earth they walked away from a salary that they will find almost impossible to match in the free-agent market, wondering whether there is any loophole that might permit them to escape from a trap in which they find themselves.