With the signing of Clayton Kershaw (7 years, $215 million), another "bar" has been set for upcoming contract extension negotiations between the Red Sox and Jon Lester. According to WEEI.com's Rob Bradford, those talks have still not started—although every expectation is that they will commence around the start of Spring Training. Whenever they begin, Ben Cherington will need to determine how close the Red Sox want to come to the 'Kershaw Territory'—both in years and cash. It's instructive to note that there's an "opt-out" clause for Kershaw after five years—when he'd still be only 30 years of age. Part of the Lester calculus will be how far into the future Boston wants to guarantee money to the lefty (especially with so many young arms near-ready in the minors). Lester is already 30 and could begin to decline at the end of any multi-year deal. Then again, maybe not. Since he became a mainstay in the rotation in 2008, he has never thrown fewer than 191.2 innings—going over 200 frames in '08, '09, '10, '12 and '13. And, of course, last year, he was 4-1 in the magical 2013 post-season run. How this ends up will say a lot about the pitching direction of the Red Sox for years to come.