jon lester feature red soxAlthough it has certainly felt like Jon Lester’s decisionĀ in free agency is now something of a first step in the Chicago Cubs’ offseason strategy for acquiring arms, we could never really know if that was certain. After all, even if Lester is the Cubs’ top preferred pitching option at this time – and there are many reasons to believe that he is – they’re going to be working on other items in tandem with the Lester pursuit, and some of those items may not be impacted by Lester at all.

Then again, Buster Olney writes that Lester’s free agency, and the perception that he could be the next big name to sign, is actually holding things up for most of baseball right now. Olney points to a few one-off things that may be unaffected by Lester – reclamation signings like Brett Anderson, unique relievers like Andrew Miller – but I don’t think he’s exaggerating when he suggests that a great deal cannot go forward until it’s known where Lester is going, and for how much. Consider that teams with starters to trade may prefer to wait until after Lester signs (and/or the receiving teams may want to wait, because they may be waiting on Lester, himself). Consider that other free agent pitchers may want to wait until after Lester sets the market, and/or puts the non-signing teams back into the market. Consider even that teams looking for offense may want to wait because where Lester lands (and for how much) could impact the offseason strategy of both the signing team and the teams that miss out on him, which could then make certain offensive players more or less available. And, because of the waterfall effect of all of these things (teams don’t have to be waiting on Lester to be held up; the MetsĀ could be waiting on, say, the White Sox and Alexei Ramirez, and they’re waiting on the A’s and Jeff Samardzija, and they are waiting on Lester), it’s virtually impossible to postulate all of the ways in which teams could be waiting on one seemingly-unconnected big name player.

Long story short: if teams and players and agents really believe that Lester is going to make a decision this coming week or weekend, just before the Winter Meetings, then there might be a whole lot of holding patterns in place. And, if Lester is the Cubs’ current top target, who could cost upwards of $135 to $150 million, I could certainly see them, at a minimum, not doing a whole lot until Lester decides.



Nick Cafardo today writes about Lester, by the way, and touches on this issue, wondering if some in baseball are growing impatient with Lester’s approach to free agency. That seems crazy – and Cafardo agrees – given that Lester has earned his right to free agency, and owes it to himself to treat the process as thoroughly and deliberately as he deems necessary. Cafardo’s piece reads like Lester is the Red Sox’s to lose, and it requires only that the come to something near the top of the market for Lester, which could wind up at six years and $150 million. The Cubs, Cafardo hears, are “very serious” about landing Lester, and the Giants are growing more serious, as well. The Yankees loom. But it still sounds like it is the Red Sox who can shut the whole thing down if they choose.

We’ll see. I expect this week to be quite heavy on the Lester rumors, so prepare yourself. There will probably be some wild swings.




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