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jon lester feature red soxFree agency is a couple months away, but teams are deep in scouting mode, planning their offseason courtships while they have a chance to see guys playing in games. I suppose it makes sense that free agency rumors would pop up a lot right now, particularly involving marquee players like A’s pitcher Jon Lester, who will be among the top arms available in free agency after this season.

Jon Heyman writes that those wistful notions of Lester returning to the team that traded him away last month aren’t really gaining traction around the game, and folks he hears from say that the odds Lester actually re-signs with the Red Sox are long. To the extent that the Red Sox do not emerge as a legitimate option for Lester in free agency, it certainly places his “money isn’t everything” comments in a new light.

Heyman points to the Cubs and the Yankees as the early top two suitors for Lester, which makes sense given the obvious needs and market size. There will be other interested teams, of course, but this isn’t the first time we’ve heard the Cubs connected to Lester.

While I certainly won’t go so far as to say, here in late August, that we already know the Lester pursuit is going to come down to the Yankees and Cubs, it’s interesting to think about how that could play out if the two teams did wind up fighting for Lester’s services. I’m unconsciously biased, of course, but as I look at the two situations, I have a hard time coming up with much that the Yankees can offer that the Cubs can’t beat or exceed – except, perhaps, for dollars. Great city, large fan base, near-term playoff aspirations, historic stuff (admittedly, the Yankees’ “stuff” is “winning championships”).

The separators, in my mind, for a guy who is sincerely interested in the things besides money, would be the five to ten year outlooks for each organization and the familiarity with the staff. On the latter, the Cubs have a front office with whom Lester is very familiar and theoretically comfortable. On the five to ten year outlook, is there really anyone who wants to argue it’s brighter for the Yankees than the Cubs? The Yankees will keep spending, but with so many locked-in long-term deals and a roster that already averages something like 32-years-old, I’ll take the Cubs over that window, especially because I happen to be of the informed opinion that the Cubs will have plenty of money to spend over the next 10 years.

It’s already a pretty safe bet that we’re going to see an Obsessive Jon Lester Watch at some point, though I’d caution you not to develop tunnel vision: there are other options out there, and the question of valuation must always be considered (rather than merely “winning” the free agent). On the right contract, I’d be quite happy about landing Jon Lester. I just have to repeat that to myself so that I don’t get carried away when that Obsessive Watch inevitably comes to fruition.

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