Ben Cherington breaks down the breakdown in Jon Lester negotiations

December 10, 2014 - 10:54 am

SAN DIEGO -- As the Cubs celebrate the arrival of their ace in Jon Lester, the Red Sox are left to answer for how it came to this -- how a pitcher who expressed a desire to spend his career in Boston, even if it meant a hometown discount, ended up heading elsewhere. Looming over that postmortem is the question surrounding the team's initial four-year, $70 million offer to Lester last spring -- an offer that was so far from what the pitcher deemed acceptable that it became, in essence, the end-point of negotiations until Lester arrived at free agency. Red Sox GM Ben Cherington -- who learned late on Tuesday night of Lester's decision in two conversations, first with agent Seth Levinson and then in a brief phone call with Lester -- addressed some of those issues on Wednesday. While he declined to go into the specifics of the team's offers (either the four-year, $70 million extension proposal in spring training that was meant to be a conversation-starter rather than an endpoint, or the team's final six-year, $135 million offer this week (the team's second offer of the free-agent process, according to Cherington, made this week after an initial offer in November following a meeting between Lester and team officials in Atlanta), which came up $20 million short of what the Cubs had on the table), Cherington offered his view of what happened in the talks with Lester. "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. But we desired to have more dialogue prior to the season and made an effort during the season and weren'€™t able to," said Cherington. "Then we got into free agency and we'€™re able to do it then. Jon did a lot of great things for the Red Sox. We wish him nothing but the best. We'€™re moving on." Here are some highlights of Cherington's 30-minute media session: ON THE FOUR-YEAR, $70 MILLION OFFER AND TALKS BETWEEN LESTER AND THE RED SOX ABOUT AN EXTENSION "The problem when pieces of conversations or pieces of information get put out without the whole context of what'€™s going on, it can sort of shape the public narrative. All I can say is that we had a lot of conversations prior to making an offer. I think there was a decent understanding on both sides of where, back in spring training, and during the season, of where the sort of range of both sides were looking. We felt that we could enter into a conversation, and we could start a conversation and that'€™s the only way you get to a deal, is to start a conversation. We just weren'€™t able to have the kind of dialogue back in the spring, or during the season, that we wanted to. as I'€™ve said before, can we learn things from what happened? Sure. Always can. But right now, once you get into free agency, it becomes a different animal. We understand that. 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. We go back to focusing on putting our team together and we feel really good about where we are." He added: "I believe there's no deal that can happen unless you're able to get in a room and talk about it. 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. I think we all, everyone involved in the process, can learn something from that: How could we have gotten in the room more and been able to have a bigger, more constructive conversation? Would it have led to a deal? I don't know; you can't guarantee that. You don't have a chance unless you're able to talk and share concepts and all that. That didn't happen enough. We can learn from that. Everyone in the process can learn from that. It is what it is. Once you get into free agency, it's a different animal. He just had offers that were above ours. He chose one and we wish him well." On whether the team felt it had adequate opportunity to talk with Lester in the spring prior to making its initial offer: "We felt like we had enough conversations to get something formally started. We felt like we had an understanding of where everyone was and what the range was that he was looking for. As I said that doesn'€™t mean we can'€™t learn things from the process and I can and we all can. I would'€™ve liked to have found a way to have a more constructive conversation in spring training, whether that means starting earlier or whatever it was, you can certainly think back and learn something from it. But that conversation that we hoped and expected to have just never happened. The lead up conversations happened but you have to, to get a contract conversation started, you have to get something on the table, get in a room and go back and forth. We weren'€™t really able to do that."

On the team's efforts to continue negotiations after making the initial offer: "Right at the end of spring training we expressed the desire to engage and a couple of times during the season we did, too. Once it got to the season, he made it clear he preferred not to do that and we honored that. ... [Lester said that he] just wanted to focus on the season. When it got close to the season it became I just want to focus on the season."

On whether the team felt it hurt its chances to bring back Lester by trading him: "Remember, we hadn't been able to have any kind of constructive dialogue about a contract in spring training or during the season. And so, we were hopeful that we would be able to do that in the offseason, but there was nothing, we hadn't been able to have any kind of constructive dialogue with him to that point. If we had been in first or second place or in the playoffs, obviously we wouldn't be trading him. But we weren't, so we had to act rationally. ... The trade was simply a product of where we were. We weren't winning, and so we have a guy who's a free agent and obviously at that point there was no certainty we were going to be able to sign him after the season. And so I talked to Jon at the time about that, and I think he knew that as we got closer to the deadline that that was a possibility. We made a decision that we felt was in the best interest of the Red Sox at the time based on the information we had. We made it knowing that our hope would be that we'd engage with him in the offseason, and we have. He's chosen to sign elsewhere. The trade was just a function of where we were in the standings." ON THE FREE-AGENT PROCESS On whether the Sox were appealing to Lester's connection to the organization in free agency: "I don't think we were trying to appeal to that. He knew that and we knew that. The incumbent so to speak, sometimes there's an advantage to that. I think Jon knew everything about the Red Sox organization. We knew everything about Jon. In a free-agent courtship, teams you're not as familiar with, you're getting the presentation. With the Red Sox, he knows everything -- all the good stuff and maybe the imperfections and vice-versa. There were no secrets. It's just, this is what it is. We expressed to him, 'Hey, we want you back. We'll give it our best shot. We understand you've got a choice to make.' Ultimately, he made that choice." On whether the team believed that Lester would take a discount to stay with the Red Sox once he arrived at free agency: "That'€™s something you'€™d have to ask him. There has been talk about that I understand. And the thing is, nobody on the Red Sox ever talked about that. That was something Jon talked about. Not in any conversation we had with him did we talk about discount or hometown, any of that. That was something he said, and when we tried to enter into a conversation in spring training, we'€™re just focused on trying to find a deal that makes sense for him, makes sense for us. I don'€™t know if his thinking changed in free agency as opposed to last winter, I don'€™t know, you'€™d have to ask him." On the Sox' ultimate six-year, $135 million offer in free agency: "We had a pretty clear idea interally of where we were willing to go at the beginning of the offseason, and we had an opportunity to go there. What we didn't know was where the market would go. In free agency, you know there's always a chance the market gets passed where that line is for you. In this case, it did. We still thought there was a chance he would come back because he had expressed a desire to be here in the past and all that, but yeah, we had a pretty clear understanding interally of where we were willing to go. We didn't know where the market would go at the beginning of the offseason, and now we know. ... We were given every chance to get to where we were willing to go. We got to where we were willing to go. And then he had a choice to make and he made it." On whether the ultimate signing price for Lester came as a surprise: "No, because we had a pretty good idea where teams were and we knew he was going to have to make a choice so we weren'€™t that surprised when the total number came out." On the disparity between the initial spring training offer and where Lester's ultimate signing price were: "When we'€™re talking about contracts and guys under contract or in control or whatever, you'€™re trying to find a space that makes sense for everyone. And every one we'€™ve done in the past, whether it'€™s younger guys or [David] Ortiz or [Dustin] Pedroia or whatever, there is a lot of conversation that happens before an offer to determine roughly where that space is. So, you try to enter into something to get a conversation started knowing you'€™re shooting to get to a space that makes sense. That'€™s what our intent was in spring training. The number that was put out there in April, something can be factual but not really capture the entire conversation. That number was put out there so it became the story. Anyway, that didn'€™t reflect our position in spring training. Jon knows that, [agent Seth Levinson] knows that. On top of that of course, now he'€™s had a full healthy season and he'€™s been really good and we'€™re in free agency so of course our position would increase based on all that new information. So that'€™s the best way to answer that." On whether the team believes Lester was going to go to the highest bidder in free agency: "That's more a question for him. We definitely felt like once it got into free agency that we were treated fairly. We were given every opportunity to put forth what we needed to put forth and to meet with him and to have any conversation that we wanted to have. The free agent process played out like most of them do for a high-profile free agent." On whether the Sox were aware of offers that included a seventh-year vesting option and or a seventh year: "We weren't given every piece of detail on the other offers. We were told generally where the other offers were in terms of total guarantee. We weren't given all the details nor should we necessarily be given all the details. That's not something I would expect. We did what we felt we could do, what we could justify, with the best we could do. We were comfortable with that and then he had to make a decision. He did." On the emotional fallout of losing a player who had been a part of the organization for 12 years: "Maybe some other day I'€™ll be able to think about that but once you'€™re in free agency, we knew this was a possibility, we were going to do our best but we knew this a possibility so we were working on so many things. We were working on things last night as soon as I got the call, you just go back to work. That'€™s what we need to do. We need to just keep working and build a pitching staff. I'€™m not sure there'€™s really time to reflect on it."