Obsessive Jon Lester Watch: Some Possible Negative Signals for the Cubs

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Obsessive Jon Lester Watch: Some Possible Negative Signals for the Cubs

Chicago Cubs

jon lester feature red soxJust about anything about Jon Lester right now begins with a note that there are some big do-ins in Boston, and they’ll absolutely impact the Lester pursuit one way or another. I don’t think we can accurately predict how just yet, but I wanted to make sure to offer it up front. Suffice it to say that it’s plausible that adding two top bats to the team could make the Red Sox all the more attractive to Lester right now.

Another possible impact of the Boston offensive maneuvering? Maybe the Yankees now see the Red Sox as an even bigger threat in the AL East, and what better way to kill two birds with one stone than to try and grab Lester? Yes, yes, we’ve heard the rumors about the Yankees not spending on any top tier free agents this offseason, but we didn’t buy it then, and we’re not buying it now. Indeed, Peter Gammons, who has recently suggested the Yankees could be lurking on the Lester periphery, said just this morning that he wonders whether the Red Sox’s Sandoval/Ramirez moves could push the Yankees into a hotter pursuit of Lester.

Even before these potential Boston signings broke, Nick Cafardo was writing yesterday that the Red Sox were worried not about the Cubs signing Lester, but the Yankees.

And then you’ve got the Giants, having possibly missed out on Pablo Sandoval, possibly ready to use the savings there to go after someone like Lester, according to Ken Rosenthal (and here, too).

On the balance, it’s hard to see how any of this is good news for the Cubs’ pursuit. And then there’s this Gordon Wittenmyer report, noting in part, “Cubs insiders did not express confidence as the season ended that they would be successful in their pursuit of top free-agent pitching target Jon Lester. And sources said they’re not especially optimistic after their meeting in the last week.”

Not to get too parse-y, but, for what it’s worth, “did not express confidence” is technically a neutral statement, not an affirmatively negative one (the opposite is “did express confidence” – would you really expect the Cubs to express confidence that they’d get Lester when the season ended? Or at any time?). Further, “not especially optimistic” is not the same as “affirmatively pessimistic.” Again, it would be a bit odd for the Cubs to have met with Lester and immediately be “especially optimistic” about their chances of landing him, especially when everyone seems to be on board with the idea that the Red Sox are the most likely destination right now.

Still, it’s probably not a great sign, all things considered. Throw in the possibility that the Yankees could now become seriously involved, too?

It will be very interesting to see how the Lester pursuit is clarified in the coming days by whatever the Red Sox are able to finalize with respect to Ramirez and Sandoval. Remember: Lester is reportedly meeting with two additional teams this week, so we’re very likely to hear some more on his market in the coming days either way. This Red Sox news probably brings it even more to the fore.

Lastly, a funny anecdote making the rounds today with word on the Red Sox agreeing to sign Hanley Ramirez. This is from a USA Today piece four years ago:

A fluffy question was posed to Lester: had he and Ramirez, back when they were in the minors, perhaps gone out for a pizza one night and talked about someday playing in the All-Star Game?

“I’d have a better chance of being struck by lightning than me and him getting a pizza together,” Lester said. “You can take that for what it’s worth. But there was no chance on God’s green earth that I was getting a pizza with him.”

So, maybe there’s not a very good relationship there between Lester and Ramirez. Or maybe Lester just hates pizza. Either way, I wouldn’t take this as any meaningful reason for Lester to avoid the Red Sox now. These guys are all pros, and I highly doubt Lester would not sign with the Red Sox solely – or even partially – because there was a guy on the team with whom he didn’t want to go get pizza.

In any case, it’s a funny story. Hopefully the Cubs don’t emphasize their Giordano’s pizza partnership too heavily in the Lester sales pitch. Or, wait a minute! Maybe the reason Lester didn’t want to get pizza back then is because he wasn’t in Chicago, and he refuses to eat any pizza that isn’t authentic Chicago deep-dish pizza!

We’re through the looking glass here, people.

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.