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Jon Lester taking his time as he weighs his decision

Jon Lester has a lot on his mind these days.Charles Rex Arbogast/AP/File

The San Francisco Giants have the money, the cachet, and the family atmosphere to offer Jon Lester.

They are three-time World Series champions since 2010. They failed to re-sign Pablo Sandoval, but in the end they didn’t want him that badly, and they have a beautiful city with rabid fans who would love a Madison Bumgarner/Lester duo for many years to come.

Question is, where will the Giants’ offer land? Lester spent the second half of last season in the Bay area, with the Athletics. Did he love it, not love it? Oakland is certainly different from San Francisco.

He’d also be in the National League, where there is no DH and weaker lineups, and in AT&T Park, which is pitcher-friendly.


So that was what Lester had to consider Monday, when he met with the Giants near his home in Atlanta. .

For sure, he is taking his time wading through his free agency offers. This is his last chance to make the right decision about his future. So he is weighing all comers, no matter how long it takes.

At this point, it would probably behoove him to get into the Winter Meetings (next week), where more teams could come out of the woodwork, including those who feel a sense of desperation.

Right now, the Chicago Cubs are going for it. According to multiple reports, they have offered Lester a six-year, $138 million deal. We know the relationships are there with Theo Epstein, Jed Hoyer, and Jason McLeod. We know the Cubs are a rising team, one that could be a powerhouse in a year or two after they acquire a couple of big-time starters.

Would it excite Lester to be part of that, in a great city, in front of a starving fan base, generation after generation who have never seen the Cubs win a championship? As special as it was for Red Sox players to experience 2004 and the end of an 86-year championship drought, imagine the euphoria after ending a 108-year drought?


The Cubs and Giants offer that National League experience. Lester also has visited Atlanta, which is now his home, but Braves president of baseball operations John Hart said that Lester is the right player at the wrong time. The Braves would need to move Justin Upton somewhere to even think about affording Lester.

And, of course, there is Boston.

We’ll see how much beyond the $120 million mark the Red Sox will go. They have so many trade chips that they could easily let Lester go and trade for Cole Hamels (and his five-year, $110 million contract), a pitcher who is comparable across the board to Lester, from to age to performance.

The Red Sox may be planning to obtain up to three starting pitchers. I’m guessing the order of preference would be signing Lester, trading with the A’s for Jeff Samardzjia, and dealing Yoenis Cespedes to the Reds for Mike Leake or Mat Latos. As we’ve pointed out before, the Reds would need more than Cespedes to make a Johnny Cueto deal work.

So the Red Sox and Lester have a lot going on.

The Red Sox have some leverage in that Lester did mention a hometown discount. So if the Red Sox go to $130 million and the Cubs are at $138 million, does that constitute a discount to go to Boston? Or are all bets off and he goes to the highest bidder?


Lester is expected to speak to a couple more teams this week. Best guesses could be the Dodgers and Cardinals. The Blue Jays are always lurking; they could use a front-end starter to go along with a pretty good staff. The Yankees could always be that “next” team getting involved.

So this is far from over.

Surely, at this stage of things the Red Sox are multi-tasking, juggling a few things. Besides the Philadelphia, Cincinnati, and Oakland scenarios, the Red Sox also have interest in Cespedes from San Diego and perhaps Seattle, which despite signing Nelson Cruz Monday to a four-year, $58 million deal still needs a right fielder. (Of course, Cespedes would have to OK a move to right.)

Cespedes is represented by Roc Nation, who also represents Mariners second baseman Robinson Cano.

The Red Sox would like to know what is happening with Lester before moving on from him and going after secondary choices such as James Shields or trade scenarios.

They will make a deal because they have to. With extra outfielders and 10 prospect pitchers between Triple A and the majors, there is not room at the inn for everyone.

The Andrew Miller derby is getting hot and heavy and could come to a head shortly. As we wrote Sunday, the Yankees are hot after Miller. They may be moving toward him and away from closer David Robertson.


The Red Sox, Dodgers, Tigers, White Sox, and Blue Jays seem all in on Miller. The money keeps rising — maybe now $50 million over four years. There is no sign that Boston is out of the finalist category.

Backup catcher?

A lefthanded bat is still the preference, and any deal with Oakland could be expanded to include John Jaso. Otherwise, David Ross is still out there, a perfect mentor for Christian Vazquez and the preferred catcher of Lester.

This has all the makings for a frantic finish.

Can the Cubs lose out on another major free agent after letting Russell Martin escape to the Blue Jays? Will the Red Sox try to save face by bidding far more than Lester is worth? Will the Giants make up for losing Sandoval by creating the Bumgarner/Lester tandem?

Stay tuned in the next week or so for the final conclusion.

Nick Cafardo can be reached at cafardo@globe.com. Follow him on Twitter @nickcafardo.