The Red Sox would very much like to bring Jon Lester back to Boston for the next six years. Their chances seem to be pretty good on that front, as the Cardinals have backed down and the only team to this point challenging them all that much has been the Cubs, who don't necessarily have the same ability to deliver on their promise of winning as the Sox. The one team that might truly get in the Sox' way, though, is the Giants, and they're meeting with Jon Lester on Monday according to ESPN's Buster Olney.
The Giants have a significant need for Lester in their rotation, as Madison Bumgarner can't pitch every day of the regular season like he seemingly did during this past postseason. Tim Hudson will be 39 and likely average at best, Tim Lincecum isn't a starting pitcher anymore no matter how hard people wish him to be, Jake Peavy is a free agent, Matt Cain is recovering from elbow surgery, Ryan Vogelsong is too up and down, and Yusmeiro Petit probably isn't the answer all by himself.
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On top of needing Lester, the Giants can afford him. Their Opening Day payroll came in at just under $150 million in 2014, and has risen $53 million since 2010's Opening Day payroll -- the Giants have won the World Series three times in that stretch and have a massive, loyal following, so it's no wonder they've pumped their earnings back into the team. They're mostly set on the position player side, lack much in the way of impact prospects to plug in to the roster, and only have $87 million on the books starting in 2016: someone like Lester, an elite free agent who doesn't carry any compensation baggage, is perfect for this team. Especially since Pablo Sandoval walked away from their bid of nearly $100 million to join the Red Sox.
Will the Giants go to the necessary $140 million or maybe even more it could take to lock up Lester? That's unknown, but the only long-term commitments they have at the moment are for Cain, Buster Posey, and Hunter Pence. In the later years of a potential Lester deal, Posey is the only other commitment on hand. They have the need, the room, and the resources, making them perhaps Boston's most dangerous competition for Lester's services. It's maybe not something to necessarily panic over, but if you did, no one would blame you.