As of Thursday, the idea of Jon Lester remaining with the Red Sox in 2015 seemed more unlikely than ever. In fact, the merits of dealing the Red Sox ace before the end of this season grows by the day.
In short: The Red Sox want Lester to blink, but with an emerging Cy Young candidacy thus far this season, and just three months until the rest of Major League Baseball can negotiate on the same playing field as the Sox, such flinching doesn't seem likely.
But before getting into that, let's set the scene.
We're sitting here less than one week before the non-waiver trade deadline and the Red Sox' playoff hopes are sunk. They have nine players who will be eligible to become free agents at the end of this season -- Jonny Gomes, Burke Badenhop, Andrew Miller, potentially Craig Breslow (if his option isn't exercised), Stephen Drew, Jake Peavy, David Ross, Koji Uehara and ... Lester.
While it is somewhat notable that the Red Sox haven't engaged in contract talks with Uehara, that really isn't the story these days. It's all about Lester. That was the case in January, February, March, April, May, June and now July.
Lester remains unsigned, and in terms of performance this year he sits atop the list of pitchers primed for free agency. He has handled himself on and off the field in textbook fashion. The momentum toward the lefty signing a mammoth deal has only gained steam as the season has progressed, with voices like John Lackey pushing it along.
“He’s an example you want to be around the young guys. He’s how you do it. He’s a pro,” Lackey said of his rotation-mate prior to Tuesday's game. “You could take him and write a book about how to be a starting pitcher in the big leagues. He works his butt off. He handles his business. He never gets into any trouble. He’s not a guy you have to worry about. He doesn’t do anything dumb. He gets it.
“I’ve been fortunate to be around a lot of good guys who do things the right way, but performance-wise and ability-wise he’s better than those guys and does it the right way. He’s pretty good.”
And about that conversation regarding Lester being worth that much-talked-about five-year deal?
"Jon’s a different deal, man. He works his butt off,” Lackey said. “He’ll be just fine in five years.”
Much has been made of the Red Sox' initial offer of four years, $70 million, as has the team's perceived misstep of not taking advantage of what looked like a healthy window to put a better foot forward in spring training. All the comps have been explored, from Adam Wainwright to Homer Bailey to Cole Hamels to Zack Greinke.
And now, with the Red Sox clearly sellers and free agency three months away, an important checkpoint has arrived.
After talking with multiple sources familiar with the situation, the following is where things seem to stand.
-- Between the email sent to the Boston Herald by principal owner John Henry as well as Sox president/CEO Larry Lucchino's comments made on the Dennis & Callahan show Thursday, it is clear the team wants to get out the message that it tried to talk deal but Lester and his agents prefer not to engage at all until season's end.
“[Ben Cherington] may still have some continuing discussion with [agent] Seth [Levinson] on other issues or other matters, but certainly the negotiation, the parties have agreed to let’s step away and do this after the season,” Lucchino said on D&C, adding: “Jon made very clear to us that that was his preference. ...
“It’s done in part out of respect for Jon Lester and his desire to postpone this until after the season. He’s on an extraordinary roll. His last five or six games, his ERA is I don’t know, 0.90 or something like that. He’s leading this team, leading the rotation, and his very strong preference, as I think you might have heard from him just a day or two ago on national television was not to have his family and himself distracted and focused on something other than pitching and winning baseball games. ...
“I’m not going to answer a question about the analysis of the stages of this negotiation, because the negotiation will continue. It will continue after the season, to be sure, but there will be an opportunity for us to resume negotiations with Jon and with his agent -- they have made that abundantly clear to us. So, looking back and doing an analysis of, ‘Was this a wrong step or was this the right step,’ would only be counterproductive."
-- According to industry sources, however, Lester and Levinson remain open to engaging in "efficient" contract talks if there is a sign the Red Sox are ready to extend an offer in line with market value. As of a few weeks ago, it was believed the vicinity of five years, $110 million-$120 million would be a conversation-starter. The pitcher has stood by his desire to not have the contract talks serve as a distraction to him or his team, hence the willingness to re-engage only if it appeared as though a quick resolution could be discovered.
"Not in my mind. I know that's been [part] of some of the conversations we've had with them, just trying to reiterate, 'Look, this doesn't change anything.' I just don't want to it to be a distraction," Lester responded to reporters Thursday morning when asked if the comments by Henry and Lucchino would mean his chances of staying with the Red Sox might be fading. "People know how things get, especially around here. ... The last thing, especially with [the trade deadline] next week and us needing to play well and get out [of last place], it's just not something that needs to be talked about or in the forefront of the plans right now. We need to play better baseball and win, and that should be the focus right now."
-- Because there hasn't been an offer perceived by the Lester camp as market value, it would be a logical assumption that the Red Sox are taking a familiar approach: getting cost certainty of an entire season -- making sure, in particular, there are no physical setbacks -- and then coming back to the pitcher after the season with an increased offer, but one most likely not meeting other clubs' interest.
What the Red Sox would be banking on is Lester's very public desire to remain in Boston. It was leverage they believed they had all along with David Ortiz. And going back a bit, it was what worked in the case of Mike Lowell (who took three years with the Sox instead of four with Philadelphia).
-- Now, with the Red Sox having dug their grave in Toronto, the conversation has to expand in regard to a potential trade of Lester. Here is what the lefty said when talking about such a scenario when appearing on The Bradfo Show podcast:
"I think every year when you get to the trade deadline, that's always a possibility," Lester said. "How great a possibility it is, I don’t know because you're not in that room, you're not making the phone calls. I think this year, given the unique situation we could be in at that time, I don't know. I always said, if they feel like trading me is going to make the Boston Red Sox better for the future, then no hard feelings. Like I said, it's business.
“I want to be here, I think they want me to be here. But like I said, at the same time, I’m sure they wanted [Adrian Gonzalez] and [Carl Crawford] and [Josh Beckett] and [Nick Punto] to be here, but they needed to make a decision for the greater good for the future. That’s what they had to do. If that's what they have to do, then that's what they have to do. There wouldn’t be any hard feelings. I would still think of my time here as great, cherish every minute that I was here, go about my business wherever I go. ... This game isn’t stable. As much as we’d like to make it stable, it's not."
Lester continued: "Like I said, if they get to that position and they feel it’s necessary, then it is. I can't stop it. I can't do anything and I can’t say anything. There’s nothing you can do. If you get traded, you get traded and you try to make the best of it. ... If they did, I’d understand. It would probably be a pretty sad time, but at the same time exciting and all those things we talked about before.
“I’ve always tried to take that mindset going into the deadline, because if you sit there and worry about it and contemplate and get on the Internet and try to figure out where you think you’re going and find out all those things, it’s just unnecessary stress and thoughts you don't want.”
While Lester has spent his entire eight-year career in Boston, he also noted that he has been mentioned in trade rumors before. He was going to head to the Rangers in the deal that swapped Manny Ramirez for Alex Rodriguez before the Players' Association nixed the blockbuster. During the 2007 offseason, Lester was one of the mentioned chips that would be dealt to the Twins in a potential trade for Minnesota ace Johan Santana. The move eventually fell through, as Santana was eventually sent to the Mets on Feb. 2, 2008.
“I think I’ve actually been traded twice and either one didn’t go through and the other one at the last second got pulled back,” Lester said. “It’s something I’ve been a part of. I think that's why I have the mindset I have now. I’ve been traded and gone back to the team that traded me, so it is what it is.
"I get a call, 'Hey, you’ve been traded to the Rangers,' OK, great. That’s cool. A day later, 'Hey, you're back with the Red Sox because the deal didn’t go through.' Obviously a lot of mixed emotions. Spring training was a little weird. Then I think the Johan Santana thing, they were trying to get him. That got pulled off the table right at the last minute."
The guess is that the Red Sox listen on Lester, but with the value of a draft pick to fall back on -- and without the opportunity for an acquiring club to get a pick -- there would need to be some severe motivation on the buyer's behalf.
(The best example of a team trading for a player in a similar situation came during last year when the Cubs traded Matt Garza to Texas for four players, including top pitching prospect C.J. Edwards and reliever Neil Ramirez, who is having a standout season in Chicago's bullpen. And Lester is at least a few notches up from what Garza represented at the time.)
Judging by the Red Sox' approach thus far, the narrative suggesting their reluctance to go to five years or beyond with the 30-year-old Lester hits at the heart of the matter. If there was that comfort level to offer such a commitment, these late July days would probably be filled with the dotting of 'i's and crossing of 't's (as was the case when Hamels was locked up by the Phillies with a six-year, $144 million deal in late July 2012), instead of ownership proclaiming we will have to wait until after the season for news.
Unless there is a dramatic change of course, this could very well be the last season (and perhaps week) you will see Jon Lester wearing a Red Sox uniform.