Ben Cherington is in no mood to play Monday morning quarterback.

The Boston Red Sox fell short in their quest to sign Jon Lester, as the left-hander accepted a six-year, $155 million contract with the Chicago Cubs early Wednesday morning. Cherington naturally is left to wonder where things went off the tracks, but the Red Sox general manager realizes several factors contributed to Lester’s decision to sign elsewhere in free agency and nothing can be done to change the outcome.

“Simply put, the Cubs offered more than we did and he made a choice, and we respect it and wish him nothing but the best,” Cherington told reporters Wednesday at the Major League Baseball winter meetings in San Diego. “We go back to focusing on putting our team together, and we feel really good about where we are.”

Many will point to the Red Sox’s initial four-year, $70 million offer back in spring training as the point at which things began to unravel. The Red Sox maintain the offer was designed to get the ball rolling, though, and Cherington’s biggest regret is not having an opportunity for further dialogue before Lester cut off negations in order to focus on the season.

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

The term “lowball” frequently has been attached to the Red Sox’s initial offer. It certainly seems worse now that Lester could earn exactly $100 million more than the offer if his seventh-year option with Chicago vests. However, Cherington felt the sides had enough conversations before the Red Sox made the offer to gain a decent understanding of where everyone stood in their contractual expectations.

“I believe there’s no deal that can happen unless you’re able to get in a room and talk about it,” Cherington said. “You might agree, you might disagree, you might go back and forth. But the only way to actually get to a deal is to be able to get in a room and talk about it.

“I wish we had been able to do that more. It doesn’t guarantee we would have gotten to a deal, but I wish we had been able to do that more.”

With a lack of constructive dialogue and the Red Sox in last place, Cherington decided in July the best move was to trade Lester with the hope of reengaging in talks after the season. Cherington said he felt the Red Sox were given a fair shake in negotiations this offseason, but, as the GM put it, free agency is a “different animal.” The market simply extended beyond Boston’s comfort zone, as the Red Sox reportedly submitted a final offer of six years and $135 million.

“We had a pretty clear idea internally where we were willing to go in the offseason and we had an opportunity to go there,” Cherington said. “What we didn’t know is where the market would go. In free agency, there’s always a chance the market gets past where that line is. In this case, it did.”

The Red Sox now are left to explore other starting pitching options, whether it’s through trades, free agency or a combination of both. Cherington can’t afford to sit on his hands with a rotation to construct.

“We need to just keep working and build a pitching staff,” Cherington said of the Red Sox’s next move. “I’m not sure there’s really time to reflect on it.”

Thumbnail photo via Mark L. Baer/USA TODAY Sports Images