Lukewarm Stove: Is Jon Lester Going to Reach Free Agency, Too?

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Lukewarm Stove: Is Jon Lester Going to Reach Free Agency, Too?

Chicago Cubs

lukewarm stoveThere was a time, several months ago, when the free agent pitching class after the 2014 season looked like it had the potential to be stacked. Clayton Kershaw, Homer Bailey, Max Scherzer, Jon Lester, Justin Masterson, James Shields, and a handful of other potentially interesting arms, too.

And then there was a time, maybe about a month ago, when it looked like the free agent pitching class after the 2014 season was going to be decimated by extension mania. Kershaw was locked up, and then so was Bailey. Lester kept saying publicly how much he wanted to stay in Boston and would take a hometown discount to do it, and Masterson made the Indians a hometown offer of his own. The Tigers cleared a bunch of salary, and seemed pretty much set to extend Scherzer. The class was looking like it would be 33-year-old Shields, and a bunch of maybes. Not exactly what you’re looking for if you’re the Cubs, who’ve rolled over money into the next offseason, and who project to be very pitching-needy in the coming years.

But then Masterson and the Indians couldn’t get a deal done, and the Tigers announced that they couldn’t reach an agreement with Scherzer. The class was once again starting to look decent.

Might it now be just about as full as we could have ever hoped it would be?

Despite public acknowledgements that everyone wanted to get a deal done, and despite a willingness to negotiate throughout the season (so don’t assume this is the end of discussions), the Red Sox and lefty Jon Lester have yet to come to an agreement on an extension. Moreover, the Red Sox’s offers so far have been strikingly low.

Jeff Passan and Ken Rosenthal report that the Red Sox’s extension offer to Lester was just four years and $70 million. Not only did Lester reject the offer, Rosenthal reports that he will no longer negotiate with the Red Sox during the season. If true, Lester will be yet another quality arm on the free agent market for the Cubs – OK, and other teams – to explore starting in November. (For his part, Lester didn’t deny the Rosenthal report, but did tell Gordon Edes that it doesn’t mean he’s out of Boston for sure. “Things can definitely change,” he told Edes.)

Outside of a blip in 2012 (and it wasn’t even that bad), Lester has been a consistently very effective starter, routinely in the 4-win, 3.50-FIP range. In this market, assuming there aren’t any health concerns, a 31-year-old lefty with those numbers probably gets a five-year contract with ease. The Reds bought out Homer Bailey’s free agent years in the $19 million per year range, so that’s probably about where you’d expect Lester negotiations to begin. Five years and $100 million is probably going to be one of the early estimates.

I would be remiss if I didn’t point out the obvious front office connection here, given that the Cubs’ crew are the guys who originally developed and extended Lester with Boston. How that kind of thing plays out in free agency, and whether it matters much, I can’t really say for sure. I think it depends on the player and the specific relationships at play. Suffice it to say, the Cubs’ front office knows the guy well, and, if he reaches free agency, they’ll do some due diligence.

Depending on the development of young players on the big league roster and prospects in the minors, the Cubs may or may not be in an ideal position to spend big on pitching this offseason. I don’t mean for these free agency discussions to suggest to you that the Cubs absolutely will be involved in upper tier pitching free agency. Instead, I think it’s important to point these things out now, because it will be nice for the Cubs to have options. They’ll have the money, the need, and (probably) the protected first round pick. That’s all I’m saying.

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.