Obsessive Jon Lester Watch: Cubs Aggressiveness, Red Sox Money, Lester Comps, More

Nov 26, 2014

Jon Lester remained the primary talk of the day yesterday in the Cubs’ world, with a report from Dave Kaplan that the team’s initial offer to the free agent lefty was “north” of six years and $135 million. Because of that, and because Lester continues to be a hot free agent target for an increasing number of teams, there’s a whole lot more to discuss on Lester today.

Speaking of that report, Gordon Wittenmyer refuted it on Twitter, citing a source who says six years and $135 million as the offer is “not accurate.” Although he did not say anything else, Kaplan responded that he stands by his source, and said Wittenmyer was wrong. There are so many semantical games you can play with the word “offer” and the amount of the offer that, even though the reports are directly contradictory, there could actually be middle ground where the two sources don’t actually refute each other as much as you might think on first impression. Only Kaplan and Wittenmyer know for sure. In a battle of anonymous sources, all you can really do is take the information at its face, and add it to the mental data bank.

Amplifying his original report, and after speaking with additional sources, Kaplan added this:

Latest on Lester: Solid east coast non-team source told me Cubs being very aggressive (135+). Team has been in radio silence… Won't talk.

— David Kaplan (@thekapman) November 26, 2014

As I wrote earlier this week, the luxury tax hit to the Red Sox, if they blew past the $189 million cap this year, is not going to be particularly painful, according to Red Sox owner John Henry. Saying that he’s “hopeful” that Lester will return, Henry made sure to emphasize at yesterday’s Sandoval/Ramirez press conference that, “The way [the luxury tax cap is] structured we can blow through one year. Again, for next year we have tremendous flexibility. So we could go could through for one year and not overly effect us.” So, the point here remains: whatever else the Red Sox do, landing Sandoval and Ramirez did not make the finances so tight that the Red Sox can’t stretch for Lester or definitely have to turn to the trade market. They can afford Lester, and they want him.

Sahadev Sharma wrote a great piece on Lester for Baseball Prospectus, and you want to give it a read. Are offers to Lester overweighting his fantastic 2014 season? Are they inappropriately ignoring the down 2012 season? It doesn’t matter in the sense that Lester is going to get an enormous contract either way, but some of the contract comps for Lester, given the huge walk year and less huge previous years, don’t look so good.

Jon Heyman wrote again about Lester as an unconventional free agent who really might not be all about the money. If that proves true, it could be a good thing for the Cubs – maybe he really does want to play for this front office, and maybe the whole Cubs mystique thing compels him – or a bad thing, if the Cubs were hoping that money would make the difference between him coming to Chicago or going back to Boston.

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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