SAN DIEGO (AP) — Red Sox general manager Ben Cherington says he wishes he had a little more conversation with Jon Lester last season.

Only hours after getting a goodbye call from Lester around 10 p.m. Tuesday before it was learned the lefty agreed to a $155 million, six-year contract with the Chicago Cubs, Cherington lamented that he wished things had gone differently when Lester was still with Boston.

"I think we would have liked to have had more chance for dialogue prior to the season," Cherington said Wednesday at the winter meetings. "Why that didn't happen, maybe there's more than one reason. I think we can certainly learn from the process. But we desired to have more dialogue prior to the season, and (we) made an effort during the season and weren't able to."

Lester had expressed interest last winter in re-signing with the team that drafted him in 2002. But after the Red Sox made in spring training a four-year, $70 million offer, Cherington said Lester and his agents were reluctant to talk again.

With team falling in the standings, trading Lester to the Athletics at the July 31 trade deadline made perfect sense for Boston. At that time, Lester said leaving the Red Sox doesn't rule out a return to the team next season.

But the Red Sox had a maximum contract offer in mind and it fell about $20 million short of the offer made by Theo Epstein, the Cubs' president of baseball operations and former Red Sox executive.

Cherington said Boston made their final pitch this week during the winter meetings.

"We were given every chance to get to where we were willing to go," Cherington said.

Now, the Red Sox need to fill two rotation spots and Cherington has said all week that he has spoken to numerous teams about free agents and trades. With the addition of free agents Pablo Sandoval and Hanley Ramirez, Boston could move outfielder Yoenis Cespedes, the main piece received from the A's in the Lester deal.