Obsessive Jon Lester Watch: Sudden Chicago Optimism and Boston Pessimism?

Dec 03, 2014

Jon Lester may be having a little fun on Twitter with his free agency tour. Check out the location on his Twitter profile. Don’t eat the clues …

Buster Olney wrote some more about the Cubs’ pitch to Lester when he was in town two weeks ago, saying that the lefty was “very impressed” by the Cubs. In that piece – which requires ESPN Insider, by the way, so I’m not going to give you everything he said – Olney also reiterated his previously-stated guess that Lester will wind up with the Cubs, and will not offer a hometown discount to the Red Sox. Now, I’m going to do a little extrapolating and guesswork, so take it with a Brett-sized grain of salt (feel free to debate whether that means it’s a large or a small grain). On Monday, Olney first stated his guess that Lester would go to the Cubs. The next morning, the post comes out in which he indicates (1) Lester was impressed by the Cubs’ presentation, and (2) there likely won’t be a hometown discount for Boston. That combination of factors suggests Olney was able to talk to someone very close to Lester, and that informed his position. But, if you were Lester’s camp, and let’s imagine that he really wanted to go to Boston – but also wanted to get as much money as possible – isn’t this precisely the kind of thing you’d be sharing with a reporter? “The Cubs’ presentation was awesome (by the way, did you see those reports that they were presently offering the most money?), and Lester is going to go to the highest bidder. Nudge, nudge, Red Sox.”

That all said: Olney is a smart guy and an excellent reporter, and it’s not like he would just parrot out there whatever Lester’s camp was telling him. Because, like me, Olney would have a slight suspicion that the entire thing could be designed merely to get Boston’s offer up. So, that is to say, if things played out like I’m speculating, Olney ran it all through his internal decision machine, and decided it wasn’t just posturing, and had some credence. Thus, after rolling this around in my head, I’ll allow it to bump up my positivity on the Lester stuff just a touch. Just a touch.

Does the slight increase in Cubs-related positivity mean there is a correlative increase in Red Sox-related pessimism? Well, I can’t say they’re connected, but two opinion-ish pieces just came out of Boston from pundits who wouldn’t bet on the Red Sox getting Lester – Boston Herald, CSNNE.

Truly, though: these waves of optimism/pessimism go in cycles throughout a process like this, and you really can’t put too much stock in the opinions/guesses/gut feelings of folks who aren’t directly involved in the negotiations (and that includes me – yes, I’m telling you to only barely listen to my own guesswork). So few people are in a real position to know what’s really going on, and (1) the ones on the Cubs’ side aren’t talking, and (2) even folks directly involved – including Lester, himself – might not yet know exactly how this thing is going to shake out.

Setting aside the Cubs and Red Sox for a moment, what about the other possible teams? Well, Peter Gammons says three GMs having pointed to a “serious new entrant” in the Lester bidding. It could be a complete surprise team – Mariners? – or it could be a team that we’ve suspected is lurking at the periphery like the Yankees or Blue Jays. If it’s a “serious” bidder, though, my money (giant stacks of limitless money) will always be on either the Yankees or Dodgers, whether it makes sense or not.

We still don’t have a ton on the Giants’ meeting with Lester on Monday, but we know it took place near Atlanta, and SFGate reports that manager Bruce Bochy was there. It would be a surprise if Lester wound up with the Giants or a mystery team at this point, but you can’t totally rule it out. I can tell you this, though: if Lester does go to a non-Cubs, non-Red Sox team, I’m betting the contract would be of the jaw-dropping kind.

written by

Brett Taylor

Brett Taylor is the Lead Cubs Writer at Bleacher Nation, and you can find him on Twitter at @BleacherNation and on LinkedIn here. Brett is also the founder of Bleacher Nation, which opened up shop in 2008 as an independent blog about the Chicago Cubs. Later growing to incorporate coverage of other Chicago sports, Bleacher Nation is now one of the largest regional sports blogs on the web.

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