BOSTON -- Two winters have passed since the Red Sox in one bold stroke shed more than $260 million in salary, unloading what they had come to view as the untenable contracts of Carl Crawford, Adrian Gonzalez and Josh Beckett to the Los Angeles Dodgers.
Rarely has a team been given such a reprieve, to suddenly have at their disposal the financial flexibility to reboot their roster, and the Red Sox took full advantage, adopting a new way of doing business in the process. No longer seduced by the most lavish prizes on the market, be it Josh Hamilton, Robinson Cano or one of their own (Jacoby Ellsbury), Sox general manager Ben Cherington still spent but spread the money around among lesser talents who required fewer dollars for fewer years.
The more prudent approach produced spectacular results in 2013, the Sox winning 97 games and a World Series when newcomers and holdovers alike outperformed projections. Not so in 2014, when much of the same cast, coupled with key rookies, produced across-the-board disappointments that resulted in a last-place finish, the team's second in three years. Worst-to-first-to-worst is no one's idea of a sustainable business model, which is what makes this offseason's retooling so intriguing.
With free agents eligible after midnight Monday to negotiate with all 30 clubs, will the Red Sox stay the course and steel themselves from entering the richest auctions, or will need trump restraint and the Sox return to their old free-spending ways?
How they answer that question almost certainly will dictate whether it is realistic to entertain the possibility that Jon Lester, the left-handed ace the Red Sox traded to Oakland in July, can be enticed to return to the team he insists he never wanted to leave. Lester should be able to command far more on the open market than what the Sox might have been able to sign him for last spring, when their opening salvo (four years, $70 million) was a nonstarter.
Sox owner John W. Henry has informed more than one audience that the team will stick to its strategy of not giving six or seven years to a pitcher north of 30 years of age, which in his view only perpetuates the recklessness the team demonstrated in giving seven-year deals to Crawford and Gonzalez that took both players past their primes.
And yet, with Lester enjoying what he termed the best season of his career, along with a stellar postseason reputation dinged only slightly by the Royals in October's play-in loss, the market for the left-hander -- and Max Scherzer, the other top free-agent pitching prize -- almost certainly will push the boundaries of how an elite pitcher is compensated.
That would seem to leave the Red Sox on the outside looking in, barring a change of heart. A more feasible alternative, given their self-imposed guidelines, would appear to be Kansas City right-hander James Shields, who turns 33 in December and won't command the kind of years that it will take to sign Lester or Scherzer.
Shields has made a successful transition from a pitcher who relied heavily on a swing-and-miss changeup to a sinker-cutter artist who can still unholster his changeup when needed and has the makeup and durability that should stave off sudden decline. He does not have Lester's October pedigree, however, which might make him a tough sell to a fan base pining for their Jonny.
One advantage the Sox have over other potential suitors is that by virtue of their last-place finish, they are one of 11 teams whose first-round draft pick is protected (the Sox will be picking seventh) in the event they sign either Scherzer or Shields, both of whom were extended $15.3 million qualifying offers by their former teams. The Sox instead would forfeit a second-round pick as compensation. Because he was traded in midseason, Lester is not eligible for a qualifying offer and thus will not require draft-pick compensation.
No other free-agent pitcher profiles as the top-of-the-rotation starter the Sox need, which is why when the GM meetings begin next week in Phoenix, Cherington almost certainly will engage his peers in trade talks. Phillies left-hander Cole Hamels looms as perhaps an even more attainable target now that Phils executive Pat Gillick says the team is at least a couple of years away from contention. Hamels, coming off a terrific season and signed through the next four seasons, will never command a better return in a trade than he can now. Oakland's Jeff Samardzija and Cincinnati's Johnny Cueto are other starters who could be in play.
The Red Sox have a surplus of young starting pitchers and outfielders they could use in a trade, although it appears unlikely they would part with their top prospect, catcher Blake Swihart. The Sox worked out Cuban slugger Yasmany Tomas on Sunday in the Dominican Republic, but while impressed, according to a league source, they are not expected to be serious bidders.
The Sox's needs extend beyond starting pitching. They need a left-handed bat, with third base the logical place to stick one. Giants star Pablo Sandoval, a switch-hitter, is an obvious candidate, but the Giants are expected to make a strong run to keep him, plus Sandoval's girth requires a judgment call for any team willing to commit the five years and $90 million to $100 million it will take.
Chase Headley, an outstanding defender who finished the season with the Yankees, is another possibility.
The Sox almost certainly will add another arm or two to their bullpen mix, though, again, it seems unlikely they'll extend themselves to bring back Andrew Miller, who might be in line for a lucrative four-year deal.
There is money to be spent -- the Sox have at least $50 million at their disposal before they would threaten the $189 million luxury-tax threshold. How they decide to spend it will define their offseason.