Did a market miscalculation result in the Red Sox signing John Lackey at the expense of a chance to get Cliff Lee? In terms of both the 2010 season and the future, the possibility exists.

After the 2009 season, the Sox identified three elite pitchers who would reach free agency in a two-year window: Lackey (last offseason), Josh Beckett (who was eligible for free agency after 2010) and Lee. The team signed Lackey to a five-year, $82.5 million deal, and inked Beckett to a four-year, $68 million extension that will run from 2011-14.

At the time of the Lackey signing, the team expected that Lee, the 2008 AL Cy Young winner who was dominant in the 2009 playoffs for the Phillies, would command a monster contract in free agency after the 2010 season. While the Sox committed significant resources to Lackey and Beckett, both pitchers almost certainly would come at a significantly lower price than Lee, assuming that the left-hander had the 2010 season that the Sox anticipated.

And so, while the Sox are expected to perform their typical due diligence in talking with Lee this offseason, the reality is that the team is all but certain to pass on the dominant force of the last two postseasons. The Sox have nearly $50 million in salary committed to six starters (Lackey, Beckett, Daisuke Matsuzaka, Jon Lester, Tim Wakefield and Clay Buchholz) next year, and seem unlikely to get involved in a bidding war for a pitcher who will command a nine-figure contract.

One can certainly suggest that the Sox should have saved their bullets to make a run at Lee in free agency after this year, in hopes of channeling his Yankee-smothering prowess. Perhaps the Sox would have been positioned to take a run at Lee in free agency had they not committed to Lackey or Beckett.

More realistically, history (Mark Teixeira, A.J. Burnett, Carl Pavano, Jose Contreras, etc.) suggests that it is unlikely that the Sox would have outbid the Yankees for an elite free agent coveted by both clubs.

THE MID-YEAR MARKET FOR ACES

But what of the idea that the Sox could have pursued Lee or another ace-caliber pitcher in the trade market during this season?

Certainly, the Sox were not expecting that the Mariners – who acquired Lee as part of the three-way deal that sent Roy Halladay from the Blue Jays to the Phillies in December – might end up dealing the 2008 Cy Young Award winner. For that matter, the Sox thought it unlikely that much if any elite starting pitching would move prior to the trade deadline.

Last offseason, the Sox’ decision to sign Lackey to a five-year contract was informed in part by an examination of the recent history of trade deadline deals. The team found plenty of examples from recent years of in-season swaps involving elite hitters.

In 2006, Bobby Abreu and Carlos Lee were impact hitters who were dealt. In 2007, Mark Teixeira had moved at the deadline. Teixeira, Jason Bay, Manny Ramirez and Adam Dunn had all moved in 2008. Victor Martinez and Matt Holliday changed teams in 2009. Typically, at least one to two All-Star-caliber hitters were dealt at each year’s deadline.

There were few starters of comparable impact who had moved in-season. In 2006, the top starters to move were Greg Maddux (by that point, a five-inning pitcher) and wild card Oliver Perez. In 2007, Kyle Lohse was the top starter to move mid-year. In 2008, CC Sabathia had commanded a wealth of prospects in moving from Cleveland to Milwaukee. In 2009, Lee had gone from Cleveland to Philadelphia for a rich prospect haul, while an injured Jake Peavy was traded by the rebuilding Padres to a White Sox club that didn’t expect the former Cy Young winner to contribute until 2010.

Over a four-year period, then, two top-of-the-rotation pitchers had been acquired for the stretch run. In the same span, nine legitimate middle-of-the-order hitters had moved. And so, the Sox – after failing to find common ground with free agents Bay and Holliday – felt that they would be well served to plow their resources into Lackey, with the notion that they could always upgrade their lineup mid-year.

“Generally speaking, it’s easier to add a bat than a pitcher during the season,” Sox GM Theo Epstein said at the press conference introducing Lackey. “So, I think our pitching staff is going to be extraordinarily deep. If we do go into the season with a mix similar to what we have right now, and a need for a bigger bat somewhere in the lineup does develop, I think that can probably be addressed during the season.”

But this year’s deadline didn’t play out that way. To the contrary, the headline position players to move were complementary types such as Jorge Cantu and Lance Berkman. Meanwhile, a rare wealth of talented pitchers changed teams.

Most notably, three recent Cy Young contenders – Dan Haren (Diamondbacks to Angels), Roy Oswalt (Astros to Phillies) and Lee (Mariners to Rangers) – changed clubs. But with Lackey in the fold, the Sox were never in the mix for any of those three pitchers.

Each of the three aces who moved excelled with their new clubs. Haren, after going 7-8 with a 4.60 ERA for the Diamondbacks, was 5-4 with a 2.87 ERA for the Halos, who have him under contract for two more years with a team option for 2013.

But even had the Sox been in the market for a dominant starter, Haren might not have been a consideration given that, at the time of the deal, he was struggling, with opponents clubbing him for 1.8 homers per nine innings over a 13-start span.

Similarly, Oswalt was showing what one talent evaluator considered clearly diminished stuff this year prior to the deadline. Despite a solid 3.42 ERA for the Astros, the 32-year-old hadn’t shown the same dominant weapons that had characterized most of his career in Houston.

But, after joining a contender in Philadelphia, Oswalt appeared rejuvenated. He went 7-1 with a 1.74 ERA down the stretch. And so, the Phillies – who also received $11 million from the Astros to subsidize the remainder of the right-hander’s contract, which runs through 2011 – are currently thrilled with their return.

The Sox might well have had the prospects needed to acquire Oswalt. After all, the return offered by Philadelphia – left-hander J.A. Happ, minor league center fielder Anthony Gose and minor league shortstop Jonathan Villar – was viewed as relatively modest, with none of the three (or even Brett Wallace, whom the Astros acquired from the Blue Jays in exchange for Gose) considered an elite prospect. A package, for instance, of left-hander Felix Doubront, center fielder Reymond Fuentes and middle infielder Oscar Tejeda would have been, at the least, competitive with the Phillies offer.

Lee would have been another story. The Sox, after all, tried to work out a deal with the Indians in 2009 that included both Lee and Victor Martinez.

Traded from the Phillies to Seattle in the offseason, the left-hander had been dominant with the Mariners, going 8-3 with a 2.34 ERA in 13 starts, but Seattle’s stunningly awful performance made him expendable. He was nearly dealt to the Yankees, with multiple reports claiming that the hired gun would head to New York in a package headlined by slugging prospect Jesus Montero.

Had that deal happened, the October landscape might have looked very different. A Yankees rotation that is currently a vulnerability would have instead represented an ominous specter for any team that had to face the 1-2 punch of Sabathia and Lee.

(Random bit of revisionist history: How lucky were the Red Sox that the Indians team that took them to the limit in the 2007 ALCS only had Sabathia and did not feature Lee? The left-hander was shipped to the minors that year. If he had been even a fraction of his 2008-10 self as a member of the Cleveland rotation, the Sox would have been hard pressed to claim their second World Series in four years.)

Instead, the Yankees deal unraveled, and the Rangers swooped in to acquire Lee (along with injured reliever Mark Lowe) for power-hitting prospect Justin Smoak, a pair of minor league pitchers (the controversial Josh Lueke and former first-rounder Blake Beavan) and minor league second baseman Matt Lawson.

Though Lee’s 4-6 record and 3.98 ERA (inflated by a rough five-start stretch in which he was dealing with a back injury) seemed relatively pedestrian with the Rangers during the regular season. But, he showed glimpses of dominance in September, and he has been nothing short of historically good in the postseason.

With Monday’s masterpiece, he is now 3-0 with a 0.75 ERA, and he is the first pitcher ever to produce three straight outings with 10 or more strikeouts in the playoffs.

And so, it seems fair to ask: Are the Red Sox watching Lee dominate the Yankees and, with hindsight, ruing what could have been but for the decision to sign Lackey?

Probably not. Certainly, the Sox had no expectation that Lee might be available in a trade when they signed Lackey. No one could have anticipated that the Mariners – viewed as a contender, if not the favorite, in the AL West entering the year – would end up dealing Lee just a few months into his Seattle tenure.

Even had the Sox been interested in acquiring Lee, it is an open question whether Boston could have acquired him. The Mariners wanted to acquire a near big league-ready slugger who ranked among the top hitting prospects in the game, whether Smoak or Montero.

Though the Sox might have been able to present an attractive package along the lines of the 4-for-1 deal that Seattle swung – say, either Lars Anderson or Anthony Rizzo, along with Doubront, Stolmy Pimentel and Tejeda – they would not have had a slugger in the Smoak or Montero class to offer the Mariners. Nor would the Sox have necessarily been willing to offer such a steep price for a rental player who was destined for free agency following the 2010 season.

GOING FORWARD

In sum, one could state accurately that the Sox misread the 2010 in-season trade market at the time that they signed Lackey to a five-year deal. But it would be difficult to suggest that last winter’s strategy cost them a shot at Lee.

During the season, there is a decent likelihood that a match would not have existed with the Mariners on a Lee deal. After the 2010 season, even without Lackey under contact, the reality is that the Sox would have been extremely unlikely to outbid the Yankees (or Rangers) for the left-hander’s services.

That being the case, Sox fans will simply have to take solace in the opportunity to root for Lee in his role as a postseason Yankee slayer this year.

As for Lackey (14-11, 4.40 in his first year with the Sox) and Beckett (6-6, 5.78), the Sox believed in the ability of both to serve as top-of-the-rotation presences when they signed them to their deals. And with four years remaining on both players’ contracts, the Sox suggest confidence in the idea that both pitchers will bounce back.

“[Lackey is] a horse who takes the ball and gives you innings and gives you quality innings,” said GM Theo Epstein the day after the season, noting that the right-hander’s performance after the All-Star break (3.97 ERA, 7.8 strikeouts per nine innings, 2.3 walks per nine) was in line with his career norms. “Certainly pitched in the second half the way we expect and look forward to that carrying over to next year.

“[Beckett is] really not avoiding responsibility right now for the year, even though there was an injury that played a critical role in the underperformance. He’s taken responsibility for it. He’s not dodging the questions. He’s going to fix it this winter,” added Epstein. “The past is usually a good predictor of the future. Last time he had an off-year [in 2006], he really bounced back. That’s what we’re looking for again.”

If that pair bounces back, then the Sox will have little reason to play the what-if game, particularly given that they will have their full complement of prospects. But for now, coming off a year when those two right-handers struggled, it is hard for the Sox – and, for that matter, 28 other teams – not to look upon a Rangers team that features Lee with a mixture of awe and envy, regardless of whether it was ever realistic for them to acquire the left-hander.