Obsessive Jon Lester Watch: Cubs Not Optimistic? Combo Deal with Jake Peavy?

Social Navigation

Obsessive Jon Lester Watch: Cubs Not Optimistic? Combo Deal with Jake Peavy?

Chicago Cubs

jon lester feature red soxWith free agency just about a week away, and with the Joe Maddon situation likely to be resolved by then, you can expect a different universe of rumors to explode very soon. When it comes to the Chicago Cubs and Jon Lester, in particular, I’m almost unnerved thinking about the pace of rumors that will be coming.

Oh, and they’ll almost certainly blow with the wind, going back and forth, driving fans crazy. But, hey, that’s what it’s like when your team is finally expected to be in on some big-time free agents, right?

Speaking of which, Gordon Wittenmyer has a very interesting piece at the Sun-Times today, and you’re going to want to read it.

On the Lester side, he notes that some sources say the Cubs aren’t optimistic about actually landing Lester this offseason, because the bidding might get crazy. Of course that always seems to be true of the best free agents, and the front office has conceded that sometimes you have to go a little crazy to get the guy you want. Will they for Lester? Will they get him? Obviously they’re interested, and Lester seems to share that interest. Even though he’ll pitch next year at age 31, you’ve got to figure that it’ll take six years to get Lester. It’s the free agency principle for big-time free agents: take the number of years you think are reasonable, and add two. That’s how much a guy will get. (Alternatively, take the number of years you think a guy will get when you’re discussing him in September, and then add one.)

The broader focus of Wittenmyer’s piece, however, is the implication – pretty much straight from Jake Peavy’s mouth – that he and Lester would like to go, or at least consider going, to a team as a package deal. That team certainly could be the Cubs, as we’ve discussed Peavy’s interest in the Cubs before. The second tier of pitching this offseason is extremely deep and attractive, however, and if Peavy is going to get something like three years and $36 million, that may not be the right avenue for the Cubs. Obviously if it made the difference in the pursuit of Lester, that might change things, but is Lester really going to take less money to come to a team because Peavy is there?

As I wrote previously, there are reasons to believe Peavy could be a nice get at two years and $20 to $24 million, but that’s about the ceiling. But with guys like Jason Hammel, Justin Masterson, Francisco Liriano, and Brandon McCarthy – just to name a handful – out there, would the Cubs leap to snap up Peavy just to try and enhance their position with Lester? I doubt it, but it’s interesting to think about.

Also interesting to think about? Imagine Peavy and Lester really did come in a package. Would you rather see the Cubs land Peavy/Lester for, say, 2/$24 million on Peavy and 6/$130 million on Lester … or Hammel/Shields for, say, 3/$30 million on Hammel and 5/$95 million on Shields?

Those numbers and names are purely hypothetical for discussion purposes. When we know that the Cubs’ explicit preference this offseason is to pick up a top tier starter and a quality second tier guy, these conversations aren’t all that unrealistic.

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.