BOSTON -- With the dust settling after an eventful Winter Meetings for the Red Sox, president/CEO Larry Lucchino expressed disappointment and regret in how the team dealt with its attempts to sign left-hander Jon Lester.
"We didn't succeed, so I don't give us a very good grade. We were trying sincerely to get him signed. We wanted him to come back here. Free agency is a special opportunity for players, it comes up only once or twice if you're lucky in a career," Lucchino said during Saturday's Christmas at Fenway event. "Right now I'm trying to focus on the future and express a sense of gratitude to Jon Lester for all he did for us, for the horse that he was for us for so many years. The successful pitcher and person that he was. I wish him luck and I'm glad he's in the other league and not in our league."
The Red Sox hoped their history with Lester and his comfort with the organization would sway him to return to Boston. He chose a six-year, $155 million deal with the Cubs over a six-year, $135 million deal with the Red Sox.
Out of contention for a postseason berth, the Red Sox traded Lester to the Oakland A's on July 31 for Yoenis Cespedes.
Lester, who made his debut with the Red Sox in 2006, tallied 110 wins and a 3.64 ERA with the club. At his best during playoff time, Lester went 4-1 with a 1.56 ERA during the Red Sox run to the World Series in 2013.
"I think [principal owner] John [Henry], [chairman] Tom [Werner], [executive vice president /general manager]Ben [Cherington], myself, we've all been around long enough. You don't enter free agency with a wide-eyed sense of optimism. It's an uncharted course, it takes a lot of different turns. It's very hard to predict how it's going to play out," Lucchino said. "We were absolutely hopeful that Jon, once he got a sense of what the market would be, would be more inclined to sign with us. As it turned out, that was erroneous."
While Lester made it known last offseason that he wanted to sign an extension with the Red Sox, he rejected a four-year, $70 million offer in mid-March and decided not to reopen negotiations with the club during the season.
"As [Ben] said, it was just a starting point. Throw out a number to get a process of sequential negotiations beginning. It didn't result in that, so obviously that was unfortunate," Lucchino said. "Absolutely we were disappointed that we couldn't continue talks. Again, as Ben has said, we tried a number of times to reengage unsuccessfully."
While Lucchino wouldn't divulge specific regrets he had during the process, he did admit that signing Lester before he hit free agency would have been ideal.
"I think in general, history probably demonstrates that you're better off getting things done before you get into the frenzy of free agency. Just look at the end result and we failed to get done what was our goal, so we are subject to criticism, and rightly so, for that," Lucchino. "There's so many steps along the way that could have gone differently."
Even though the team lost out on Lester, Lucchino remains optimistic about the Red Sox moves this offseason, including a revamped rotation encompassing Wade Miley, Rick Porcello and Justin Masterson.
"It's been a sort of unpredictable offseason in a lot of ways. So much of it was centered on our effort to sign Jon Lester. When we did not succeed in that, we had to revert to plan B, with respect to pitching," Lucchino said. "But I do feel very good about chapter one, which was the signing of the two best offensive players on the market in Hanley Ramirez and Pablo Sandoval. Ben was quick to get those things done, which gave us a pretty good start to the offseason."
Quinn Roberts is a reporter for MLB.com. Follow her on Twitter at @qlr5001. This story was not subject to the approval of Major League Baseball or its clubs.