jon lester feature red soxAlthough the Chicago Cubs reportedly had him into town yesterday for some discussions, some wooing, some wining, and some dining, we don’t know if the other big thing took place while Jon Lester visited: some negotiating.

Did the Cubs talk numbers? Did Lester or his reps? Did the Cubs make Lester an offer?

And did Lester tell the Cubs about the offer that he may have already had at that point?

In the wee hours of the morning – you are dedicated, Gordon Edes – here’s what Edes tweeted out:

Edes must have just found out about the offer – perhaps in the middle of the night – because he had written about Lester and the Red Sox just shy of midnight last night in a post about how nothing was doing on the Lester and Pablo Sandoval fronts, although meetings had taken place. That ESPN Boston piece has now been updated to clip out the Lester part (though you can see in the URL that it used to be there), and a new Lester-specific piece is up from Edes, which essentially says that the Red Sox made the offer at some point earlier in the week, before Lester met with the Cubs.



I am belaboring this a little because I’m intrigued that Edes appears to have found out about the offer to Lester in the middle of the night, perhaps a day or two after the Red Sox made it, but only a few hours after Lester’s visit with the Cubs concluded. I’m really not drawing any conclusions there, I just think it’s interesting to think about the timeline. Did the Red Sox try to get Lester to pull the trigger before meeting with the Cubs? Was the Red Sox’s offer coming through around the same time as those new rumors about the Braves and Cardinals were getting out? Were those rumors actually a response to the Red Sox’s offer?

In any case, Lester now has an offer in-hand from the Red Sox, and the negotiations – with every interested team, really – are underway. Edes says a quick decision is not forthcoming, which means that Lester will take the time to hear from other teams. What you never know for sure with free agents is whether they’re truly open to being convinced by each and every team with whom they speak, or if they’ve got a clear preference for one team, and then speak with other teams as a means to get the most money out of the team they want.

Hopefully we catch wind of the Red Sox’s offer. It’s a pretty safe guess that it’s six years and a touch more than $20 million annually. Everyone knew that was going to be the minimum required to land Lester, and, given the relationships involved (and Lester’s repeated statements that money won’t be the deciding factor for him), I wouldn’t fault the Red Sox for trying very hard to get Lester at the very minimum it takes.

That said, when it comes to top tier free agency in the last five years, it always seems like the contract the guy eventually gets is at least one year longer, and about 10 to 20% higher in AAV than folks expect. For Lester, that would mean something like a seven-year, $175 million deal is what it’s going to take. I know. That seems borderline insane. But when was the last time a top tier free agent signed a deal and you¬†didn’t think it was a little insane?



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I remain excited about the chance¬†that the Cubs could land Lester, and I know that they are very sincere in their efforts to get him. But I do want to make sure I’m appropriately bracing you for the possibility that the Red Sox have always had the inside track, given the relationships and comfort in play here, and the likelihood that the money is going to be very close on any serious offer. From the outside, it looks like this: the Red Sox made a mistake in lowballing Lester before the season with their $70 million extension offer, they then had a down year, have obvious rotation needs, and now have ownership directly involved in trying to get Lester back. Doesn’t that seem like the story of a team that’s going to do whatever it takes to get this particular pitcher?

And, if they do, there will be some serious gnashing of the teeth by Cubs fans who feel like it’s a here-we-go-again situation. I won’t be among them, first because of everything I just wrote, and second because there seriously is so freaking much quality pitching available over the next 15 months. It’s the refrain Theo Epstein and Jed Hoyer keep saying again and again. There’s a reason, and it’s not just to brace fans for the possibility that the big name won’t drop this offseason. It’s because it’s overwhelmingly true. After Lester, there are still Scherzer and Shields, and some great second tier guys. And there’s Yang. And there might be Maeda and Kaneko. And then there’s a possible Hamels trade. Or a Mets trade. Or a Padres trade. And that’s all pre-2015. From there, you’ve got Price. And Zimmermann. And Cueto. And Latos. And Fister. And Samardzija. And Porcello. And so on and so forth.

Hopefully the Cubs do land Lester, and hopefully it’s on a not-insane contract (though, at this level, as I said, they’re always a little insane). But, if they don’t, and especially if Lester goes to the Red Sox, I’m not going to be surprised, and I’m not going to be able to dwell in disappointment for too long.




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