Looking back and forward with Jon Lester and the Red Sox

September 29, 2014 - 7:02 am

Once again, Jon Lester will occupy center stage in the postseason. The left-hander is slated to start the Athletics' one-game playoff against the Royals on Tuesday night, his opponent (in almost comical coincidence) Kansas City ace James Shields. With Lester on the mound following a 16-11 season, career-low 2.46 ERA, career-high 219 1/3 innings, 220 strikeouts (9.0 per nine) and career-low 48 walks (2.0 per nine) and on the cusp of free agency, the baseball world will be watching closely. That, of course, includes the Red Sox organization that traded him on July 31 (along with outfielder Jonny Gomes) for Yoenis Cespedes. The negotiations -- or lack thereof -- between the Sox and Lester after the pitcher had stated a desire to sign a long-term deal to remain with the Sox, even if it meant taking a discount to do so, lorded over the Sox' season. That was true while Lester was with the team, and it's true now that he's gone, given that the Red Sox make no secret of the fact that they have a significant amount of work to do regarding the rebuilding of their rotation, and more specifically, the front of their rotation. "Hopefully we can get right back into it if we fix the top of the rotation," Red Sox COO Sam Kennedy said. "That's absolutely our intention," team chairman Tom Werner said on Sunday about whether he believed that the Sox could build a rotation to return to contention in 2015. "We have the resources. Hopefully it will all fall into place soon." That would represent a contrast to how things developed with Lester. The negotiations in spring training represented little more than a false start, and even with the possibility of middle ground apparent, the initial gulf between the two sides was such that there wasn't a great deal of movement in negotiations. With hindsight, Werner was asked, was there regret about the shape that negotiations with Lester took? "No. I don't want to go back too much, but let me just say that we expected a little more dialogue back and forth than happened," said Werner. "But I'll take our share of the responsibility in that." By contrast, Kennedy suggested that the fact that dialogue between the two sides was amicable left little ground for regret. "There's a lot of stuff that probably went on behind the scenes that is not for public consumption," said Kennedy. "I think we feel really, really good about the way both sides handled the discussion. Very positive." While the two sides did not find common ground during the season, the Red Sox seem likely to pursue Lester anew this winter. Whether there is a greater likelihood of an agreement come November remains to be seen, though Kennedy suggested that characterizations of the Sox' philosophical rigidity -- particularly a bright line unwillingness to go beyond deals of four years for pitchers in their 30s -- may not be accurate. "I don't know what we will do or won't do, but I would be surprised if we wouldn't consider every and any option -- whether that means a long-term deal for a pitcher over 30, I don't think there's any hard and fast rules," said Kennedy. "I think there's a philosophy and empirical data that shows [deals of five-plus years for pitchers in their 30s have] not worked in most situations. But I've never heard, we don't do this, we don't go long on a pitcher, we don't go more than six years, or seven years. "There was a lot of talk after the Dodgers trade about what we were going to do or not do vis-a-vis existing players. We traded Adrian and Carl Crawford and Josh Beckett. And then shortly thereafter, we made the deal with Dustin Pedroia. Having a long-term extension with a player going well into his 30s." Does that mean that the Sox, who would not have to wonder about Lester's fit for Boston or whether he has a routine that would give him at least a chance to sustain success into his 30s, might make another serious run at Lester? "On the pitching front, I don't know. I really don't know what will happen. I think a lot will depend on the market and what the market looks like," said Kennedy. "Obviously, I'm not at liberty to say one word about any potential free agents but I said before the trade that I was hopeful we would have certain players here for a long time. I'm hopeful that we're active in the free agent market."