Red Sox have work, explaining to do

SAN DIEGO -- The Boston Red Sox lost their high-risk game of attempting to re-sign Jon Lester as a free agent after an ill-conceived attempt to sign him to a contract extension in March and then trading him in July, losing Lester to the Chicago Cubs and a six-year, $155 million deal that includes a vesting option for a seventh year.

Boston's final offer was for six years and $135 million, only slightly higher than the six-year, $132 million ceiling predicted by a team source to ESPN Boston at the general managers' meetings last month in Phoenix. The Red Sox's offer did not include a vesting option for a seventh year; Boston's original offer to Lester last March was four years and $70 million, meaning they nearly doubled the money and tacked on two more years before Tuesday's coup for the Cubs.

General manager Ben Cherington's pledge to rebuild the starting rotation just became exponentially more difficult as the Red Sox were outbid by former Larry Lucchino protege Theo Epstein for the services of Lester, whom they had clearly and repeatedly identified as their top pitching target this winter. Lester becomes the second top pitcher to come off the market this week, as the Oakland Athletics traded a top-of-the-rotation starter in Jeff Samardzija to the Chicago White Sox.

Former Detroit Tigers right-hander Max Scherzer shared top billing with Lester among free agent pitchers, but Scherzer turned down a six-year, $144 million offer from the Tigers last spring. Scherzer, a client of agent Scott Boras, reportedly is seeking an eight-year deal in the $200 million range, which would seem to eliminate the Red Sox from consideration.

A more likely free-agent alternative for the Red Sox is right-hander James Shields, who turns 33 on Dec. 20 but has proven to be extremely durable, with eight straight seasons of pitching 200 or more innings. Shields has shown some slippage from the days he was the ace of Tampa Bay's staff, but he was 14-8 with a 3.21 ERA for the American League champion Royals in 2014, averaged 7.1 strikeouts per nine innings while walking just 1.7 per nine, and had an ERA-plus of 124. Because he is older, Shields would seem to be in line for a contract of shorter duration than Lester's and for an average annual value considerably less than his $25.8 million, the second highest ever given to a pitcher.

Shields's agent, Page Odle, is almost certain to meet with the Red Sox before the winter meetings end Thursday.

On the trade front, Phillies left-hander Cole Hamels, who is just a month older than the soon-to-be 31-year-old Lester, is the most logical pitcher for the Sox to target, although Hamels, who is under contract control for the next four seasons, figures to command the highest return in a trade. Hamels is owed $94 million over the next four seasons, an average of $23.5 million. Because the Red Sox are one of the teams on Hamels' no-trade list, they almost certainly will be asked to pick up a $20 million team option for a fifth year.

Hamels had a modest 9-9 record for the Phillies last season, but he posted a career-best 2.46 ERA and struck out 198 batters in 204 2/3 innings. Like Lester, he also is a proven postseason performer who has thrived in a high-intensity environment. With the Phillies in rebuilding mode, they will seek top young prospects in return.

Their wish list will almost certainly include Mookie Betts, who may be the team's best position prospect and projects as an everyday outfielder in 2015 for Boston. The Red Sox will probably try to offer a package that will not include either Betts or catcher Blake Swihart but could include shortstop Deven Marrero, young center fielder Manuel Margot or third baseman Rafael Devers, and a pick among several young arms, such as lefties Henry Owens, Eduardo Rodriguez and Brian Johnson.

One major-league source insisted Tuesday that the Phillies have had little trade conversation centering on Hamels this week, but that should change quickly.

There are any number of pitchers who are a year away from free agency who could be available in a trade.

The Washington Nationals are entertaining offers for right-handers Doug Fister and Jordan Zimmermann, but are looking for help at second base and third base, which doesn't match up well with the Sox, especially with Will Middlebrooks coming off consecutive down years.

Two major league sources said the Detroit Tigers, to date, have little interest in trading right-hander Rick Porcello for outfielder Yoenis Cespedes. Cespedes is likely to be dangled to the Cincinnati Reds, who have four pitchers entering their walk years: ace Johnny Cueto, Mat Latos, Mike Leake and Alfredo Simon. Cespedes also might appeal to the San Diego Padres, who so far have fallen short in their quest to add an impact bat, losing out to the Sox on Pablo Sandoval and to the Diamondbacks for Yasmany Tomas.

Allen Craig and Shane Victorino are other potential trading chips, but both are coming off injuries; another is Jackie Bradley Jr., an exceptional defender who may be given a chance to regain his batting stroke by another club.

Shadowing whatever moves Cherington makes will be the perception that the Sox badly mishandled negotiations with Lester, an integral part of two World Series champions and a homegrown talent who ranked very high among the team's all-time best left-handers.

In essence, the Red Sox set up Lester fans for two major letdowns -- the trade in July to Oakland, and then being outbid by $20 million by the Cubs, raising questions why the Sox did not do more to bridge that gap.

No Sox officials responded to requests for comment Tuesday night, but soon enough they will be called into account. They will be hard-pressed to prove that they can build a pitching staff without Lester that will be as good as one they could have had with him.