Slugger Prince Fielder's nine-year, $214 million deal with the Tigers underscored the unpredictable nature of free agency. (AP)

As the Red Sox prepared to reload after missing the playoffs in 2010, they faced something of a dilemma. They could part with three of their top prospects in an effort to acquire a superstar first baseman, or they could wait until after the 2011 season when there would be a potential once-in-a-generation ensemble of first basemen on the market.

The Red Sox, of course, chose the former route. Though it hurt to part with pitcher Casey Kelly, first baseman Anthony Rizzo and centerfielder Reymond Fuentes, the Sox were willing to do so to acquire Adrian Gonzalez on the condition that they were able to define the parameters for a long-term extension. The team chose that path not just because of its longstanding love affair with Gonzalez, but also because they were happy to avoid the murky terrain of free agency, a process that at times resembles a descent into dark underworld of Dagobah in which one never knows what one will encounter.

As one Sox official pointed out last spring, you simply never know who will jump in the bidding in free agency for a player and take him out of a reasonable price range. Moreover, the fact that the free market is not transparent further complicates the bidding process.

It’s become popular sport to ridicule the notion of the so-called mystery team, but suffice it to say that at the start of the offseason, no one anticipated that Prince Fielder would end up signing a nine-year, $214 million deal with the Tigers. Few thought that Albert Pujols would leave St. Louis in order to sign a 10-year, $254 million deal with the Angels.

Would the Red Sox have been able to afford either Fielder or Pujols on the sorts of deals that they signed, or Gonzalez for whatever he might have commanded on the open market? Maybe, maybe not. But what the Sox knew was that they could take the three-prospect needed to trade for Gonzalez and that they could afford his $6.3 million salary in 2011 as well as the seven-year, $154 million extension that will kick in next year and run through the 2018 campaign.

The Sox knew that they had a comfort level adding Gonzalez for his age 29-36 seasons at the value they established in negotiations with him. Whether they would have been similarly confident in the return on investment if they had to sign him through, say, his age 38 season, or if they had to pay Pujols through his age 42 season or Fielder through his age 36 season (given the likelihood that erosion of his somewhat limited defensive skills will turn him into a DH at some point in his deal) is not as clear.

All of that serves as something of a reminder about how difficult it is to plan to build through free agency. Unlike the trade market, which offers cost certainty, free agency inherently features guesswork that either can lead teams to bid against themselves or that forces them to blow past commitments with which they could expect performance to remain in line with contract size.

While Pujols and Fielder received the third and fourth contracts of $200 million or more in major league history, the Sox remained comfortably on the sidelines as the bidding process unfolded. It is hard to imagine that they were unhappy with that vantage point.

A look at the three first basemen:

PRINCE FIELDER

27 years old (turns 28 in May)
9-year, $214 million contract with the Tigers ($23.8 million per year)
2011: .299 average, .415 OBP, .566 slugging, .981 OPS, 38 homers, 120 RBI, 162 games
2006-11 average: .282 average, .391 OBP, .541 slugging, .932 OPS, 38 homers/year, 108 RBI/year, 160 games/year

Fielder is the youngest of the bunch, at an age that suggests he is just entering his prime, and that he’s likely to be the healthiest of the players over the coming few years (despite concerns that his massive frame will make it difficult for him to remain hold up for the long haul). He also put up huge numbers in 2011.

He’s been somewhat less consistent than Gonzalez and Pujols, having alternated MVP-caliber numbers with star (rather than superstar) level production in the last six years. His year-by-year OPS since his rookie year of 2006: .831, 1.013, .879, 1.014, .871, .981. His defense is also a notable step down from that of past Gold Glovers Pujols and Gonzalez, and the likelihood that he spends the life of his next contract as a first baseman (rather than a DH) is low.

Moreover, he has benefited from his home park, with a .965 career OPS at Miller Park and an .896 road mark. Still, his power is extraordinary, and his ability to impact a baseball while unloading with a monster swing bears resemblance to David Ortiz.

ADRIAN GONZALEZ

29 years old (turns 30 in May)
7-year, $154 million contract with the Red Sox ($22 million per year)
2011: .338 average, .410 OBP, .548 slugging, .957 OPS, 27 homers, 117 RBI, 159 games
2006-11: .297 average, .380 OBP, .520 slugging, .900 OPS, 31 homers/year, 103 RBI/year, 160 games/year

Gonzalez had his fewest homers since 2006, a development that was at least partly the result of the fact that he lost strength in his surgically repaired shoulder over the course of the year and that he suffered a mid-year neck injury that hindered his ability to drive the ball.

However, removed from the offense-smothering environment of PETCO Park in San Diego, he also performed near an MVP level, with the highest average and OBP of his career, along with the second highest slugging mark. Moreover, Gonzalez is in the middle of his prime.

With a healthy offseason of workouts in front of him, there is reason to believe that he is capable of sustaining or improving upon his 2011 performance in the coming couple of seasons, so long as he remains relatively healthy.

ALBERT PUJOLS

32 years old (turned 32 on Jan. 16)
10-year, $254 million contract with the Angels ($25.4 million per year)
2011: .299 average, .366 OBP, .541 slugging, .906 OPS, 37 homers, 99 RBI, 147 games
2006-11: .325 average, .424 OBP, .613 slugging, 1.037 OPS, 41 homers/year, 118 RBI/year, 152 games/year

Pujols is the oldest of the three, and he is at the end of what is typically a player’s prime offseason seasons, at a point where decline typically sets in. His career-low average, OBP, slugging percentage, OPS and RBI total suggest as much.

That said, his production was still remarkable, particularly given that he shook off a poor start and that he missed just two weeks after suffering a wrist fracture in the middle of the year. And he still assaults baseball’s with nearly unmatched force.

With Pujols, it is nearly impossible that anyone else can match his peak years. The question is whether the coming peak years of Fielder and Gonzalez might prove superior to the early years of his decline from his historic heights.

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Victor Martinez may have played his last game as a Red Sox. (AP)

Red Sox catcher Victor Martinez said after his team’s season-ending victory over the Yankees that he did not know what to expect from his pending venture into free agency, though he reiterated how much he had enjoyed his time in Boston and the idea that he would like to come back.

“I said earlier, I want to be here, but now, that I got a chance to go out to free agency, we’ll see what happens,” said Martinez. “It was one of the best experiences in my career, to come here, wear this uniform and play in front of these great fans. It’s unbelievable. The competition, to come here and just be ready to play every day, it was amazing, and an honor for me just to wear this uniform.”

That said, Martinez suggested he had no idea what to expect in terms of the likelihood that he returns to Boston or heads to another city (including cities with rumored interest, including Detroit and Baltimore). He had no idea what kind of timetable might be followed for talks with the Sox.

“You’ve got to talk to them. It’s not up to me. I think I did my part, which is just to go out there and play. Now I’m going to go home, be with my family, and see what happens. … I think I’ll be alright to find a job somewhere,” said Martinez. “Like I said, I’m just going to go home, relax, enjoy my family a little bit, just wait for a phone call or something.”

While there have been questions about whether Martinez’ future is as a catcher or first baseman, he said that he would prepare this offseason in the same way that he has in the past, in anticipation of serving as a catcher. He also said that he will continue to view himself as a catcher “until my body says no.”

“You look at my stats, and just because I play a few games at first base, it doesn’t mean that I’m a first baseman,” said Martinez. “I’m just going to go into the offseason, prepare myself like I always do, work hard, and come back next year, whatever I’m going to be, and play hard like I always do.”

Martinez, who missed a month this year due to a broken left thumb, hit .301 with a .351 OBP, .493 slugging mark, .844 OPS, 20 homers and 79 RBI in 127 games. He played 110 of his 127 games as a catcher. Among catchers with at least 300 plate appearances, Martinez ranked among the leaders in batting average (2nd), OPS (2nd), OBP (5th), slugging (1st), homers (tied-2nd) and RBI (1st).

Jason Bay stopped by the Virtual Press Box to take questions as part of WEEI.com’s weekly baseball chat series. The transcript of the chat — in which Bay discussed life playing for the Red Sox and in Fenway Park, his career path, teammates such as Kevin Youkilis, Dustin Pedroia and Jonathan Papelbon, and some aspects of his impending free agency — is below:

How is it playing in left field with the Green Monster?

Jason Bay: Playing left field in Boston is great for a few reasons. The history of the wall and all the players who have played there in past years make it really special. I think that the monster is a little intimidating at first, but after getting used to it, I really like the nooks and crannies and the effect that it has on the other team and players who aren’t used to it.

Hey Jason…did you find that Fenway helped your offensive production in comparison to playing in a park like PNC?

Jason Bay: It’s definitely a whole different comparison when you’re talking about PNC Park and Fenway. The monster is very close and left center field in Pittsburgh was roughly 400 feet, so I would say that the Green Monster didn’t hurt my offensive numbers. That being said, I think more than the ballpark dimensions, the team I had around me in the lineup probably had a greater effect. When you have a former MVP, a guy who steals 70 bases and numerous high on-base percentage guys hitting in front of you, it makes it easier.

Jason if you could attribute one reason to the unfortunate early playoff exit for the Sox what would that be?

Jason Bay: I can’t give you one reason. It was a combination. It was no secret we didn’t hit very well. Now do you attribute that to good pitching or poor hitting? I say it was a combination of the two.

Hey Jason, what’s the most important factor for choosing which team you will sign with?

Jason Bay: There isn’t one important factor. The funny thing is that everybody has an opinion of what I’m waiting or or what I’m doing and I don’t even have an opinion, and that’s the truth

Phillies or Yankees and why?

Jason Bay: It’s funny, after playing baseball all year I don’t really pull for one team or another. I just enjoy watching it.

What is it like playing for Tito, and of all the teammates and coaches you have played with, who in particular has really helped you elevate your ability?

Jason Bay: Really, really enjoyed the atmosphere that he created. Boston is one of those places there is a lot of media and he does a very good job of not letting that affect his decision and let everybody does their job. I really enjoyed Brad Mills also, and wish him the best. He has great people skills like Tito, and like it or not that’s what a manager needs.

Who do you think will win the Stanley Cup?

Jason Bay: The Vancouver Canucks for the hometown call

How do the Pittsburgh fans compare to Boston fans

Jason Bay: Pittsburgh and Boston are very similar in their passion for sports. Obviously the Red Sox have had more success lately than the Pirates, but if you ever had a chance to go to a Steelers or Penguins game you would understand the two cities have a lot similarities

Hey Jason, I was just wondering what your favorite moment as a Red Sox has been so far?

Jason Bay: Scoring the winning run in the clinching game of the ALDS against Anaheim on Jed’s base hit

How many HRs do you think the Monster took away from you this year?

Jason Bay: I would say a couple but at the same time I probably got more than a few doubles that would have been fly outs anyplace else, so I can’t complain

The right field fence at the New Yankee Stadium is really only 270 feet from home, right? I mean even Pedroia knocked one over that thing.

Jason Bay: I don’t think it matters how far the fence is. I think it’s the same thing as Fenway. Both teams have the same amount of opportunities. It’s kind of like the weather. It’s really a wash. As for Pedroia, it seems like once a week he’s claiming that if a certain pitcher gets him out one more time he’s going to quit

Jason, ever gotten tips from Jim Rice on patrolling LF in Fenway?

Jason Bay: Jim is always in the clubhouse and around the guys and has numerous times offered bits of info. He always makes sure to mention the history of the guys that played there before me … hah, hah

Are you spending the offseason with a heavy training regimen…or relaxing at home and enjoying the offseason?

Jason Bay: As of right now relaxing but this Monday the offseason program begins again. I go to an athletic training institute and do a lot of running, jumping, stretching … not your conventional bench press and biceps curls.

All things equal, would you rather play on the west coast? We always hear you are a “west coast guy.” How much will that play into your decision this offseason?

Jason Bay: The window for my career doesn’t last forever so limiting myself to one geographical spot really has no bearing on my decision

There was a recent article about Youkilis, that he has a negative relationship in the clubhouse. How do you feel about him as a teammate?

Jason Bay: I definitely don’t feel the same way. Youk is obviously a great baseball player and a great teammate, on the field and off. I think his intensity sometimes gives people a skewed reality of the type of person he is, but I would take him on my team every single time

When would you like to get a contract signed seeing we’re on the topic?

Jason Bay: Ideally, I would like to know where I would like to be sooner rather than later, but understand there is a process to this as well

Hi Jason, Congrats on the new citizenship. Is sister Lauren still pitching the softball?

Jason Bay: Thanks for the pat on the back for the new citizenship. But for all you Canadians who religiously go to WEEI.com, I am still a Canadian citizen. My sister is happily retired, married and enjoying motherhood

Jason, where do you stand on the “existence” of clutch hitters? Most stat-geeks (like me) will scream from the mountaintops that they don’t exist. I think they do in that some hitters are able to mentally adjust better than others to the pressure situation at hand (most of the time). What are your thoughts?

Jason Bay: I definitely think that certain guys have the ability to rise up in certain occasions, but it’s very hard to quantify that with a statistic. I think you understand and get a better feel for that just by watching certain players perform. Obviously you aren’t going to get a hit or strike somebody out in every big situation. But if a guy is statistically superior in the statistical “clutch situations,” is he more “clutch” than a guy who doesn’t do much all regular season and wins a handful of playoff games?

Jason, When John Kruk said you have “dank” hands at the plate, was he giving you a compliment or was her being coy?

Jason Bay: Your guess is as good as mine

Were you shocked and disappointed that Papelbon did not win the Nobel Prize (again!)? I know I’m still dealing with the let down…

Jason Bay: Say what you want about Pap, you always know where you stand with him and there is no gray area. Sometimes people don’t like to hear it but he’s not hiding anything and you have to respect that

Given your background — 22nd round pick, traded a bunch in the minors, etc. — could you have ever imagined being in this free-agent position? Do you think back at all about that career path?

Jason Bay: Obviously I didn’t take the most direct path to the big leagues but I think it has an effect on the type of player and person that I am today. It has always helped me keep things in perspective and therefore this whole free agent position I’m in, I’m trying to treat like any other year and whatever happens, happens.

Seattle and SF have massive left fields to play. Just sayin’.

Jason Bay: I played in Pittsburgh for five years

Jason Bay: This was the first time I’ve done an online chat and I really enjoyed the questions and the genuine interest from everybody. We’ll see many of you next year????

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.