Jon Lester has put it in no uncertain terms: he's willing to offer the Red Sox a discount in order to stay in Boston.
It's been better than a month since we first heard that Lester might be willing to leave money on the table, but at the time the quotes weren't completely clear. Lester said he wanted to stay in Boston, and knew that likely meant a team-friendly deal in the same vein as Dustin Pedroia's, but he never quite put the two together and confirmed he'd be willing to give the Sox a discount.
It's pretty hard to misinterpret this, however:
It's like Pedey. He left a lot of money on the table to stay here. That's what he wanted to do. I understand that. That's my choice, that's his choice.
I understand that to stay here you're not going to get a free-agent deal. You're not going to do it. You can't. It's not possible. You're bidding against one team. I understand you're going to take a discount to stay. Do I want to do that? Absolutely.
It all sounds like great news for the Red Sox, but...
But just like they want it to be fair for them, I want it to be fair for me and my family.
A discount is, of course, a relative thing. It all depends on what the baseline value is for Lester in free agency, which is something that an extension would keep a mystery. That baseline has been the center of some debate recently thanks to some big-name contract signings, with both Masahiro Tanaka and Clayton Kershaw breaking the bank in the past week.
Jon Lester really doesn't fit into either of those brackets. The Yankees went over-the-top on Tanaka with dreams of acquiring one of the best pitchers in baseball, not unlike the Red Sox with Daisuke Matsuzaka all those years ago. There's a good deal of uncertainty that comes from signing a pitcher who has never played in America, but with that uncertainty comes the chance for incredible heights. And Kershaw...well, it's hard to compare anyone in the game to Kershaw.
That's not to say Lester isn't good, but his 2012 season was a wreck, and even in a resurgent 2013 he wasn't nearly as good as he had been from 2008 to 2011. A big playoff performance has perhaps boosted his perceived free agent value higher than it should be, considering that Matt Garza might sign for four years and $52 million (that particular deal is in limbo at the moment). It's hard to imagine that Lester is looking to give the Red Sox a discount on that price.
If Lester views himself as a top-line free agent, then even at a discount his price might be more than what the Red Sox are willing to pay. If he views himself somewhere between that and the level Matt Garza could be placing himself at, then it's a lot easier to see the two sides come together. His flexibility will help, but the situation still comes down to two price points: Boston's maximum, and Lester's minimum. And there's no guarantee those two will overlap.