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Red Sox setting up for busy offseason

PHOENIX -- In the same sun-kissed hotel where John W. Henry's purchase of the Boston Red Sox was approved almost 13 years ago, not far from where Dustin Pedroia lives, Theo Epstein cut a Thanksgiving deal with Curt Schilling and Ted Williams' head is kept on ice, Sox general manager Ben Cherington returns with a mandate to do some serious business.

Saddled with the dubious distinction of being the first general manager in Red Sox history to finish in last place twice -- sandwiched around the 2013 World Series title, of course -- Cherington arrives for the MLB general managers meetings at the Arizona Biltmore. He will spend the next three days meeting with fellow GMs and player agents, laying the groundwork for what promises to be an active winter of reshaping the Sox's roster.

Cherington is not expected to return home Thursday with any players in tow. Typically, things do not happen that quickly in baseball, although last year Cherington had barely returned from the GM meetings in Indian Wells, California, before he executed his first offseason trade, striking a deal with Milwaukee to acquire reliever Burke Badenhop. The sinkerballer proved to be a useful piece in the Sox's bullpen, but enters this winter as a free agent.

Cherington will be on the lookout for more relief this winter, although he already locked up his closer, Koji Uehara, with a two-year, $18 million deal before Uehara could test free agency. But undoubtedly the majority of his time will be spent determining the most feasible ways he can rebuild the top of a starting rotation that was hurled into the void when the Red Sox traded away Jon Lester and John Lackey at the July trading deadline.

He also has signaled his intention to look for a third baseman -- the switch-hitting Pablo Sandoval is a target -- and must decide whether to re-sign David Ross or pursue another backup catcher.

The most obvious option open to Cherington, and one the Red Sox have rarely hesitated to employ in the past, is to simply buy a couple of starters. Part with enough dollars -- and the vault is full, with the Sox having at least $50 million to spend in 2015 before pushing the luxury tax threshold -- and the Sox could easily re-sign Lester, who has said he'd like to come back. Or they could pursue the other two top pitchers on the free-agent market, former Cy Young Award winner Max Scherzer or longtime workhorse James Shields, whose pedigree is only slightly less impressive than the other two.

Of course, if it was only about money, the Sox never would have let Lester go. They would have signed him to a contract extension long before he became the object of what promises to be a high-stakes auction, one that will not be for the fainthearted. But the boss -- Henry -- has determined, with considerable evidence at his disposal, that the risk-benefit ratio of giving a contract of six or seven years' duration to a player who has passed his 30th birthday, especially a pitcher, rarely tilts to the team's side.

Lester and Scherzer both are expected to find suitors willing to go where the Sox say they will not. Scherzer already turned down a six-year, $144 million offer from his former team, the Tigers, which shows you where his agent, Scott Boras, calculates the market is headed.

Cherington has said he expects to have a "constructive conversation" with Lester and his agents, Seth and Sam Levinson. Unless the Sox bend to the demands of the market, the most constructive part of that conversation may be an exchange of addresses for future Christmas cards.

The other avenue available to Cherington, then, is to trade for a topflight starter or two. Though a daunting proposition, and one that may cost Cherington some good prospects, it should be noted the Sox have had some striking success going that route.

Think of the best Sox starters of recent vintage.

Pedro Martinez came in a trade. Schilling came in a trade. Josh Beckett came in a trade. The price for Beckett was high -- top shortstop prospect Hanley Ramirez and pitcher Anibal Sanchez. The other two, not so much. Dan Duquette traded Carl Pavano for Martinez, a future Hall of Famer. Epstein dealt Casey Fossum, Brandon Lyon and Jorge de la Rosa for Schilling, another Hall candidate.

Two other starters who had notable success for the Sox -- Tim Wakefield and Derek Lowe -- came even cheaper. Wakefield was signed as a released player by Duquette. Lowe came with Jason Varitek in the Heathcliff Slocumb deal, another Duquette master stroke.

Now consider some of the starters the Sox signed as free agents. Steve Avery. Matt Clement. Daisuke Matsuzaka, a special case. Even Lackey, at $82.5 million by far the most expensive free-agent contract given to a pitcher by the Sox, was a disappointment until he came back from Tommy John surgery.

The trick, for the Red Sox or any team, is to identify which pitchers will help you the most, and preferably will cost you the least. There are some intriguing names that could be available via trade. Some of them, such as Cole Hamels of the Phillies, you've been hearing for months. But he is hardly alone. There's Jeff Samardzija of the Athletics, who is a year away from free agency and could command $10 million in arbitration this winter. Or Johnny Cueto of the Reds, another free agent in waiting. The San Diego Padres have three starters -- Ian Kennedy, Andrew Cashner or Tyson Ross -- who are worth taking a look at.

What do the Red Sox have to offer in return? They have what seems to be a surplus of outfielders, but upon closer inspection, the numbers are not as abundant as they might appear.

Shane Victorino, coming off back surgery, is a huge question mark. Allen Craig fell off the radar last season. Yoenis Cespedes is a year away from free agency. New Cuban signee Rusney Castillo is an unproven commodity.

So, for that matter, is Mookie Betts; for all the great promise he showed, he still has just 212 big league plate appearances under his belt. The Sox were blown away by Xander Bogaerts at the end of 2013, and how did that work out? Bogaerts and Betts remain young players with high ceilings, but so was Will Middlebrooks when he hit 15 home runs in his first 75 games, and nothing has come easy since. It's hard to envision the Sox parting with Cespedes' power without lining up another power bat somewhere.

The Sox have young pitching they can trade, though how highly the prospects are regarded by other clubs given their indifferent results on the big league level remains to be seen. Left-hander Henry Owens, who finished 2013 in Triple-A Pawtucket, may be the most attractive pitching chip, but one the Sox probably won't relinquish unless it's for a Hamels-type deal. Catcher Blake Swihart is regarded as the team's top prospect, and may be as close to an untouchable as the Sox have.

As for Sandoval, a report by ESPN.com's Buster Olney on Sunday suggests that any excitement about a Panda sighting on Yawkey Way may be short-lived. Olney reported that the Giants were optimistic about retaining their charismatic third baseman. If that is the case, the Sox may turn to free agent Chase Headley or explore a trade for Cubs third baseman Luis Valbuena.

Cherington is now staring at an empty canvas. He hopes the picture begins to come into focus this weekend.