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jon lester feature red soxAlthough they probably aren’t the only two teams trying to land lefty Jon Lester this offseason, it has felt like a battle between the Chicago Cubs and Boston Red Sox for a little while now. That feeling was only heightened when reports out of Chicago and Boston noted that Lester and/or his reps would soon meet with contingents from each organization, complete with ownership in tow, in order to be wooed to Chicago or to return to Boston.

At the time, it sounded like Boston was going to try and make their meeting happen late last week, and maybe even get Lester to sign before he had a chance to come to Chicago, which is expected in the next few days.

Apparently, Boston didn’t have that chance:

It’s kind of amazing how much information Gammons packed into that single tweet. For one thing, as indicated, Gammons is implying that the Red Sox did not meet with Lester prior to Saturday, as they’d reportedly hoped to do. Just a scheduling issue? Lester wanting to hold off both teams until this week? Erroneous initial reports?

Who knows, but it’s probably mildly good news that the Red Sox might not get a several-day-lead in trying to sway Lester. There’s always been a small part of me that is concerned that, if Lester goes to Boston to visit with management, they don’t let him leave until he’s signed (a la Rafael Furcal and the Dodgers back in 2006). That may still be possible, but maybe not. Heck, maybe now the Cubs get the first meeting.

Also in Gammons’ tweet, the ever-looming presence of those Yankees. Despite multiple reports that they’re going to sit out the high-end pitching market this year, they’re also there as a deep-pocketed possibility to pounce. I doubt they would come completely out of left field and announce a surprise signing, however, so I’m guessing that, if the Yankees become involved, we’ll hear about a meeting.

And lastly, there’s that December part. We’ve heard conflicting things on the likely Lester timeline, with some hinting that Lester would sign much more quickly than most top free agents, with Jed Hoyer suggesting that he thought the high-end market might not really evolve until early December (Kap and Haugh), with others saying none of the big pitchers would sign until December, and now with Gammons saying Lester could last into December. To that, I would say that it’s always a smart bet that any nine-figure free agent will last at least into December, even if Lester felt like a guy who might go more quickly.

Conservative guess at this point? We’ll see Lester meeting with the Cubs and Red Sox this week, those negotiations – and possible meetings with other teams and negotiations with the same – will continue into next week, and perhaps Lester will make his decision over the Thanksgiving weekend, about which we may or may not hear rumors. That could mean an announcement might not come until early December, before the Winter Meetings. There’s a lot of money at stake here, and folks will take their time enough to get it right.

I know the rumors have been fast and furious this year, but it really is exceptionally rare that an upper tier – or even second tier – free agent signs, officially, before Thanksgiving. Last year, however, we did get word of the Yankees agreeing to sign Brian McCann, and the Cardinals agreeing to sign Jhonny Peralta in the days just before Thanksgiving.

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