BOSTON (CBS) – While you were in bed, the biggest MLB free agent shoe dropped early this morning.

30-year-old lefty ace Jon Lester agreed to terms with the Chicago Cubs on a six-year deal worth $155 million dollars around 1:30am this morning Eastern time, forcing many Red Sox fans to wake up in a bad mood — and rightfully so.

The Red Sox front office took Jon Lester’s kindness for weakness, and made him an embarrassingly low four-year contract offer for $70 million in spring training. At that point Lester walked away from the negotiating table, bet on himself, had a great season and cashed in for $85 million more than the Sox original offer.

WBZ-TV’s Dan Roche joined 98.5 The Sports Hub’s Toucher & Rich Wednesday morning to help sort everything out.

“Do you believe that if the Red Sox were to make the same offer as the Cubs that Jon Lester would still be in Boston?” Rich asked Roche.

“Yes. But [owner] John Henry didn’t want to go there. That’s their business model and that’s kind of how it is. Whether you like it or not at least you respect that. [Henry] wasn’t willing to go $25 million-plus on an average annual value,” said Roche. “They made him an offer worth $22.5 million AAV (six years $135 million) and they stuck by it, trying to get to him emotionally to finish his career with the Red Sox.”

Some folks believed the Red Sox effort to sign Lester this offseason was merely for to look good in the eyes of the fan base — a phony offer to save face with the paying customers.

The Red Sox fell far short last spring training, and in the end they fell short again to the tune of $20 million. So how bad did the Sox really want him?

“I think they wanted him, but at that price. I think they tried as hard as they could to get him for that price. I don’t think it was necessarily for show in the sense that John Henry flew to Jon Lester’s house twice, and met with him and tried to get him to come. I just think it was a different pitch, because they weren’t going to outspend everybody, as we’ve seen. All the offers seemed to be higher. I think [Henry] tried to pull at his heartstrings,” said Roche.

“I think the Red Sox felt they made a huge mistake with that four years and $70 million, but they also had a belief that they weren’t going to get to the $150 million mark. I do think they made a sincere effort to sign him once they realized the mistakes they made.”

Listen below for the full discussion:


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