Obsessive Jon Lester Watch: Red Sox Offer Reportedly $110 to $120 Million, Dempster Discusses Cubs

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Obsessive Jon Lester Watch: Red Sox Offer Reportedly $110 to $120 Million, Dempster Discusses Cubs

Chicago Cubs

jon lester feature red soxThis morning, Gordon Edes reported that the Boston Red Sox have made an offer to Jon Lester. We still don’t have a precise figure, but the guess here was that it was for six years, and something slightly over $20 million AAV. Even if there is Boston goodwill remaining, it’s virtually impossible to see Lester accepting a deal shorter than six years and for anything shy of $20 million AAV, thus, it stands to reason that’s a good guess for the Red Sox’s first offer.

Sean McAdam adds a little more information to the mix, including the fact that the offer (and the meeting with the Red Sox) came late last week, which makes the timing of Edes’ middle-of-the-night report on the Lester offer all the more intriguing. McAdam reports that the Red Sox’s offer was “aggressive,” and was longer than four years (the length of the Red Sox’s low-ball extension offer before the season). That could be five years with an above-$20 million AAV, or it could be the kind of six-year offer I’m envisioning, or, I suppose, it could be even higher. To be clear, I’m not really sure how much we can take away from McAdam’s report, given the amorphous character of “aggressive,” and our pre-existing expectation that, of course, any realistic offer to Lester would be longer than four years.

That said, McAdam does question the legitimacy of the Braves’ pursuit of Lester, and you can read his piece for more on that.

UPDATE: Nick Cafardo drops a number:

That’s obviously a touch lower than I would have expected, but pretty close. It’s a reasonable starting point, but, unless Lester is absolutely set on going back to Boston, it’s probably a good bit lower than the final deal will be (with whatever team). It’s looks clear that Boston wasn’t planning to try and blow everyone away with the first offer to get a deal done immediately. This thing is going to take time.


Meanwhile, on the Cubs’ side of things, a day after their meeting with Lester, Ryan Dempster was on The Game with David Kaplan and David Haugh this morning, and you can listen to the interview here.

Dempster, who pitched with Lester in Boston in 2013, was pretty adamant that Lester’s interest in the Cubs is genuine, and not just designed to drive up his price from someone else. In fact, Dempster said Lester was already asking him questions about being in Chicago and with the Cubs all the way back in 2013. Dempster wasn’t going to say the Cubs are a favorite or anything like that, and he emphasized that anything can happen, but he did say that, “I do know the chances of him coming [to the Cubs] are greater than him going to a lot of different places. I know he genuinely loves the city of Chicago and he’s really, really excited about the possibility of playing with a team that’s going to be good in years to come here.”

It goes without saying that, sometimes, in free agency, players will do what they have to do in order to get the best offer they can from the singular team they want. With Lester, it doesn’t sound like that’s what is happening here with respect to the Cubs and Red Sox. So, even if I still view the Red Sox as the likely spot for Lester, at least we know the Cubs have always at least had a shot.

And it sounds like Dempster is doing some recruiting for the Cubs, too, which is nice.

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.