jon lester feature red soxBack in August, Jon Lester spoke relatively glowingly to the Boston Herald about his time with the Boston Red Sox, despite the low pre-season contract offer and the July trade. Among his comments at that time is something that’s look pretty prescient four months later: “In the greater scheme of things, we’re talking about just a stupid amount of money,” Lester said of free agency. “For me, I want to be comfortable. The way I look at it is, if someone gives you $170 million and someone gives you $150 million, is that $20 million really going to change your lifestyle?” From the sound of things, the Cubs are willing to go to $150 million on Lester, but the question is whether an over-the-top offer from, say, the Dodgers ($170 million, maybe?) could sway him. And, if those same Red Sox are anywhere close to the top of the market for him, will Boston be the place he was talking about being comfortable?

Speaking of Boston, we discussed last evening the owner’s recent visit to continue selling to Lester, his second face-to-face with Lester this offseason, which could have meant any number of things – last ditch effort? final courtesy? increased offer? showing complete commitment? – so I don’t think it’s worth trying to extrapolate meaning beyond “the Red Sox are probably still trying to sign Lester.” I find it interesting, however, that in the wake of that news, there are no fewer than three new articles out of the Boston area about how getting Lester is not really critical for the Red Sox. There’s this Boston Herald piece about how the Red Sox could turn to Max Scherzer if they don’t get Lester. There’s this Providence Journal piece about how the Red Sox could turn to the trade market if they don’t get Lester (with a sprinkling of missing-out-on-big-contracts-is-often-a-blessing-in-disguise stuff). And there’s this Boston.com piece about how the Red Sox just plain don’t need Lester, specifically, given the other options out there.

Three articles with the same tenor coming out of Boston more or less at the same time, immediately after news of an owner visit and no other indication that the Red Sox’s pursuit was in some kind of trouble.



Can we make anything of that? Probably not. It’s conceivable that Red Sox insiders are putting out the word – off the record – that they don’t like their chances on getting Lester, which has prompted various writers to start setting up alternatives, which puts them ahead of the curve. But, even if it’s true that the narrative is emanating with the Red Sox, it’s just as plausible that this has been done to get some word out there that the Red Sox have tons of non-Lester options, so they don’t need to raise whatever offer they have out to Lester. That is to say: it could be part of a negotiating tactic by the Red Sox, who don’t actually think they’re out of this thing at all.

See what I mean when I say we probably can’t make much of it? I just like to think about these things.

Among the other Lester bits out there right now …

  • Are the Red Sox willing to get up into that $150 million range? We don’t know for sure – the last generally-accepted-as-true offer we heard about was six years and $110 to $120 million, and there was probably a willingness to go to $130 million – but Gordon Edes has reported an update. Edes hears from a source that the Red Sox are willing to offer “at least” $132 million. It remains entirely plausible to me that the Red Sox have decided their ceiling on Lester is in that range, and they’re hoping the lure of coming back to Boston will be the deciding factor. The Cubs, then, for their part, may have decided that an extra $20 million or so is as much as they can offer to try and overcome that lure.
  • There’s an interesting FanGraphs piece to remind us why teams are so interested in Lester in the first place – he’s really good. It’s easy to lose sight of that as you start to just focus on the pursuit, itself, and the dollars. Although there will be some regression at the margins from his career-best 2014 season, it doesn’t look like he’s a reasonable candidate for serious regression, because there wasn’t a ton of flukiness to his season. (I suppose this is also a reminder that if the Cubs are fortunate enough to get Lester, they’ll have to seriously consider adding a couple other impact players sooner rather than later, because Lester’s best years are likely to be the next couple, not several years down the road.)
  • Everyone is expecting a deal to be struck between Lester and his new (or old) team this week at the Winter Meetings – though folks were expecting a deal last week, too. Peter Gammons says the decision could come on Wednesday. The meetings last until Thursday, but, historically, folks start to head out by mid-day as the Rule 5 Draft is the focus, and various talks have concluded. Then again, there are sometimes big deals that Thursday morning – word of Albert Pujols’ huge deal with the Angels in 2011 came Thursday morning.





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