Obsessive Jon Lester Watch: Cubs Believe He's Going Back to Red Sox? Phillies Scouting Red Sox?

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Obsessive Jon Lester Watch: Cubs Believe He’s Going Back to Red Sox? Phillies Scouting Red Sox?

Chicago Cubs

We’re starting early today, I guess.

Peter Gammons was just on CBS Sports Radio and apparently said this (I didn’t catch the interview):

Gammons was then on the Dennis and Callahan show in Boston, and he phrased it this way:

I wish I’d heard the interviews live, because you can sense a fair bit more context that way. In print, however, the best we can discern from this is that Cubs sources may have told Gammons that they believe Lester will return to the Red Sox. What does that actually mean? Well, it doesn’t mean that Lester to the Sox is a done deal, otherwise the Cubs wouldn’t be going through the rigamarole of meeting with Lester and his reps today, as they are reportedly doing.

Instead, it means that, based on conversations he’s had with people who probably are in a position to know, Gammons has gotten the sense that some Cubs sources, if they are guessing, believe that Lester will ultimately decide to sign with the Red Sox. That could mean those Cubs sources do not feel confident about their potential offer(s) to Lester. It could mean that those Cubs sources believe Lester wants to return to Boston. Or it could mean some kind of combination of those things that, on a gut level, suggests a most likely outcome. Or it could be a little gamesmanship playing out between two teams competing for the same player.

And then you have to add a layer of processing, because Gammons says that this is all a “feeling” he’s gotten, as opposed to something definitive he’s been told. Of course, it could be something definitive that he’s been told, because nothing in “feeling” precludes that possibility.

That is all to say, while Gammons’ comments don’t seem to look too good for the Cubs, and you can certainly add them to your repository of information, I’d caution you against going too far with it at this stage. There are so many things these comments could mean, all possibly true, and not all of them end with Lester actually signing with the Red Sox. Remember: on Sunday, folks involved in the bidding thought Russell Martin was going to the Cubs. By Monday morning, he was going to a different team involved in the bidding. In sum, I take from Gammons’ comments only this: people in a position to know some things about the Lester pursuit believe the Red Sox are very serious about trying to bring him back. We already knew that, I suppose, but this gives it a little more oomph.

Let’s be very clear about something so that you don’t get your headspace all screwed up: once it became clear that the Red Sox were very serious about bringing Lester back, I think it was very hard to believe the Cubs could remain the favorites to land Lester. Yes, he has familiarity with the front office, but he also has familiarity with many folks in Boston. And that’s the city where he lived for almost a decade. That’s the team that drafted and developed him. And it’s a team with a ton of money, and a resolve to un-make the mistake they made when they lowballed him earlier this year. I still think the Cubs have a shot here, but I’m also keeping things in perspective.

Also: Yankees, eh? That was well-timed, given this morning’s report on the Yankees and Max Scherzer. Maybe Lester is genuinely interested in the Yankees, or maybe he’s hoping they’ll come in to push the price up on the Red Sox or Cubs. And frankly, if you’re the Yankees, wouldn’t you want to at least try and push the price up on the Red Sox? I guess maybe that won’t be possible without going so far that you risk Lester accepting a deal with which you’re not comfortable, but you’re the Yankees. If the Lester bidding is about to get bananas, it’s going to be because the Yankees started sniffing around.

Separately, but relatedly …

It’s worth pointing out the persistent rumors about the Phillies engaging the Red Sox in trade talks about Cole Hamels. Just this morning, Ken Rosenthal reports that the Phillies have been doing “background work” on the makeup of Red Sox youngsters/prospects Mookie Betts, Matt Barnes, and Christian Vazquez. While I can’t envision a scenario where the Red Sox would include Betts in a Hamels deal, it’s pretty clear that the work the Phillies are doing is in anticipation of a possible trade. Would the Phillies still be doing that work if they knew that the Red Sox were confident they would land Lester? Or is Boston preparing for the possibility of trying to add both Lester and Hamels this offseason?

I don’t think we can rule that out, and, in that regard, the two stories may not actually have anything to do with each other.

Author: Brett Taylor

Brett Taylor is the Editor and Lead Cubs Writer at Bleacher Nation, and you can find him on Twitter at @BleacherNation and @Brett_A_Taylor.