Jon Lester has made his intentions clear, telling Alex Speier he wants to stay in Boston. And what's more, he might actually be willing to give the team a discount if that's what it takes:
Lester on possible extension: 'Boston's my home... It's all I want to know.'— Alex Speier (@alexspeier) December 6, 2013
Lester said wasn't hard to leave millions on table in 1st extension, and understands if he wants to stay, has to be OK doing the same— Alex Speier (@alexspeier) December 6, 2013
The Red Sox have not been known for giving out big contracts these last few years. The one exception has been Dustin Pedroia--an extension to a home-grown player which involved said player leaving tons of money on the table. It's the situation Lester cites to Speier, and while he's not necessarily fully committed to taking that step, it would be awfully strange to acknowledge both a desire to stay in Boston and what that would take while being fully opposed to making those sacrifices.
That's not to say Lester is about to sign on at $14 million a year. Even after following up a miserable 2012 with a mixed 2013 performance, Lester's playoff dominance--six earned runs in 35 innings of work--combined with the late-season surge that put him in line to start the first game in all three series has left him looking like a highly desirable free agent-to-be. Even if Lester is willing to leave "a ton of money on the table", there's every chance he's going to be expensive.
Still, even for a Red Sox team that's looking rather averse to risk, there's no better big contract to sign than one that should by all rights be bigger. It's something they might well be working on now, waiting to announce it until later to avoid Collective Bargaining Tax implications, or it might not come up until later next year. For now, though, Lester has put the possibility out there. It's a big first step.