Jon Lester would’ve said ‘probably yes’ to 5-year/$120 million offer last spring from Red Sox

By Ryan Hannable on December 18, 2014 at 8:46 pm ET

Former Red Sox pitcher and current Cubs pitcher Jon Lester joined the Hot Stove show Thursday night with Mike Mutnansky, Rob Bradford and Alex Speier to discuss what the free agent process was like, what the negotiations last spring training were like with the Red Sox, and also what it was like the hours and days following officially signing with the Cubs.

Lester signed with the Cubs for six years and $155 million, with a vesting option for a seventh year.

Everyone keeps coming back to the reported 4-year/$70 million offer the Red Sox gave to Lester during spring training last season. What if the Red Sox came in with a higher offer — such as the Cliff Lee, 5-year/$120 million deal — would Lester have accepted?

“That is one of those deals where hindsight is 20/20. You go back in time and you look at it and you go, ‘probably yes,'” said Lester. “I mean you don’t know. I mean it is one of those deals where when it is sitting in front of you that is a lot of money to turn down. That would have made it very difficult to turn it down.”

Following spring training, Lester and his camp were under the impression the two sides would not discuss a contract during the season because that was what was agreed between them and the Red Sox, and they didn’t want any distractions for he and his teammates during the year.

“As far as I understood, and that is not coming from my agent, that is from what I understood coming out of everyone’s mouth was that once the season started, I think we had all agreed upon that and it wasn’t just one side saying we don’t negotiate during the season,” Lester said. “I think it was more a group discussion and a group decision that if we weren’t able to come to a conclusion with the contract negotiations before the season started we thought it was in the best interest of everybody to table it ’till the offseason and wait until the season is over and all the distractions of playing, the ups and downs of the season and all that to get after it again.

“Like I said the other day, I don’t know if that is a bad quality or a good quality, but I am kind of hard-headed when it comes to that. If we make a decision one way or the other, just like if we would have made the decision to continue talking I would have expected that to continue. I think we all kind of decided at that time with the distractions of everything going on it wasn’t the right time or place to continue the discussions.”

Following are more highlights from the interview. For more Red Sox news, visit weei.com/redsox.

On why he took to Twitter the day after the announcement, responding to positive and negative tweets: “It was tough. It was one of those deals we felt like we needed to do. I sat down with my wife and a couple of my buddies and anytime we got an off the wall tweet from somebody we all stepped back and took a breather — obviously not respond too fast and get ourselves in trouble and say something that we want to say, but we can’t.

“For me the best part about it was the welcoming of the new fans, the new city and the new home and obviously saying the good byes to the people we needed to. That to me was truly special and something that I will always remember — the people who truly support me and my family no matter what uniform I put on really meant a lot to me. That is why we felt like we needed to do, get out there and show these people their voices really were heard and that they are appreciated.”

On what he did the days leading up to the decision and how hard it was to escape: “I know on Sunday night I went down and saw a buddy of mine in South Georgia and got away that night and did a duck hunt on Monday morning, and stopped by my farm Monday afternoon and sat in the deer stand. It is one of those deals where you are sitting in the deer stand and getting text after text after text from people, ‘Hey where are you going? When are you deciding? Hey, what is going on? What’s the deal?’ so forth and so on. It’s one of those deals where no matter what you try and do you can’t fully get away from it till it’s done. Obviously this last week has been a whirlwind tour for us as well. It’s been a long week and turning around this week and then you have Christmas the following week so these next couple of weeks are hectic for us, but I wouldn’t complain one bit.”

On the phone calls to former Red Sox teammates once making decision: “That whole night wasn’t easy. The whole plan behind everything was to not tell anybody. We weren’t even going to tell our families when we made the decision and try and make it through the physical and then tell everyone once we passed the physical, to make sure everything went well. We didn’t want to say we signed for whatever with this team and then two days later something happen and you’re back down to nothing. We tried to go that route, but obviously I got a text shortly thereafter we made the decision saying that it was going to get out so I started making phone calls.

“Ben Cherington was number one and then Dustin Pedroia was number two shortly thereafter. After that it snowballed from there. I was calling around to guys that played a big part in my life and my career, even if they were there for a year, or a year and in half in [Shane] Victorino and [Mike] Napoli. Obviously guys like David Ortiz, I wanted these guys to hear it from me and not some tweet or not some report on MLB or anything like that. I had to make sure that they heard it from my voice and I hope they appreciated that. It was a hard night and after all those very difficult phone calls I got a pretty cool one from Theo [Epstein] and Joe Maddon and Jed Hoyer shortly thereafter. Tough night followed by a big celebration after that.”