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jon lester feature red soxSure, there’s probably only so much more the Chicago Cubs could learn about lefty starter Jon Lester that they don’t already know. Not only does this front office have many years of intimate experience with the former Boston ace, but, after so many years in the bigs, Lester has a firmly-established scouting track record.

That said, when you’re heading into an offseason where you might consider making a significant financial commitment to something as constantly imperiled as a 30/31-year-old man’s left arm, you’re going to want to get as much information as possible about how that arm is holding up. To that end, I’m reminded of something Cubs GM Jed Hoyer said earlier this year about the post-Trade Deadline portion of the season: it’s the last chance you get to scout guys aggressively in games before the offseason.

Thus, with the Oakland A’s in town to play the White Sox, it should be no surprise that the Cubs had folks in attendance to watch Lester’s start last night. According to Bruce Levine, the Cubs had Pro Scouting Director Joe Bohringer checking out Lester’s start.

We’ve talked at length about the possibility of the Cubs seriously pursuing Lester after this season. We know that the need is there, the money is there, and the fit is there. I find it wholly realistic that Lester could be the Cubs’ singularly top target in free agency this offseason, even as they will, of course, develop simultaneous plans, and back-up plans, and back-up-to-the-back-up plans.

In tandem with Lester’s visit, Patrick Mooney writes about the possible pursuit, reporting in part that multiple industry sources tell him the Cubs will indeed target Lester this offseason. No surprise there, but always useful to pile more data onto the ever-growing build-up.

If you’ve missed any of the previous Lester-Cubs rumors/takes, you can check them out here, here, and here (among others). In short, there are reasons to believe Lester is open to coming to the Cubs, and there are reasons to believe the Cubs are ready to pony up to get a pitcher like Lester. However, it’s not like the Cubs will chase Lester in isolation, with the Yankees and Red Sox possible big-time suitors, as well. Throw in a few more teams, and you’ve got a situation where actually getting Lester is not only expensive, but also not guaranteed.

In any case, I sense an Obsessive Watch coming in a few weeks.

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