... multiple sources connected to teams interested in Lester have told WEEI.com that the Dodgers are a late entrant into the sweepstakes, with both serious interest in the top left-hander on the market and the resources to make a hard, late charge.
This Boston Herald column says Lester is "gone" if the Dodgers are in the hunt:
Los Angeles could give Lester $160 million and end the bidding today. The only hope for the Red Sox would be Lester choosing the comfort and familiarity of Boston over a new start on the West Coast, which the Georgia resident seemingly has little attachment to despite hailing from Washington state. But taking a hometown discount of $5 million-$10 million is one thing. It’s asking something else entirely to take one of $20 million-$30 million. No one could blame Lester for following the money. It’s important to note we don’t yet know what the Dodgers are planning to offer. It’s possible they’ve already made one. What we do know is that, even more than the Yankees, Los Angeles is the tyrannosaurus whose arrival in a free agent negotiation makes rivals quake.
This is all true and the article correctly points out that the Dodgers have paid little or no attention to the luxury tax under their new ownership. If they've wanted a player, they've simply gone out and spent the money they thought was required.
None of this has bought the Dodgers anything but the most expensive payroll in the major leagues. Their $300 million pitcher, Clayton Kershaw, has flamed out each of the last two years in postseason games against the Cardinals. For all the money they've spent, they went 5-5 in the postseason in 2013, losing the NLCS, and lost a division series three games to one against the Cardinals this past season.
Whether getting the most money means more to Lester than playing for the Red Sox, where he has familiarity with the team and city, or the Cubs, where he has familiarity with the management team, is unknown. Most of you will probably say, "He'll take the most money no matter what." That's usually true, but when we're talking about money likely to total between $135 and $160 million, does that really matter? Would he really even notice that much of a change in his lifestyle for a few million less?
I don't necessarily agree with the notion that Lester is "gone" to the Dodgers. Many free agents who have signed for "the most money" with the Yankees over the last 14 years haven't gotten to win with all that money, as the Yankees have won just one World Series since 2000.
At a certain point, it has to be about the player being comfortable with the work environment he's going into. I don't think any of us have any idea how Jon Lester feels about that.
The only thing we can guess about is that we could find out about his choice this week, in advance of the Winter Meetings, which begin Monday. Or not. Only Lester knows his own timetable.
I'm running out of interesting Lester photos to run with these posts. For that alone, I hope he signs soon, and with the Cubs, so we'll have photos of him at a news conference trying on a Cubs jersey.
And speaking of uniforms, if Lester does wind up coming to Chicago, he'll have to select a different uniform number than the one he's worn since 2007. The Cubs have retired that number -- 31 -- for Fergie Jenkins and Greg Maddux.