|Lester wants to stay, but does Boston want to pay him? (MSN FoxSports)|
With that in mind, the Sox need to figure out what they're going to do about free agent-to-be Jon Lester. Because if the Red Sox aren't going to reach deep into their pockets to pony up what it will take to re-sign Lester, they need to deal him so they aren't left empty-handed when he signs somewhere else next winter.
Lester has repeatedly stated that he wants to stay in Boston with the team that drafted him in 2002 and won a pair of World Series with him in 2007 and 2013. He doesn't like change, doesn't want to leave, and would be willing to take a small discount to keep his socks red.
But Jon Lester's not an idiot. He knows what he's worth, and it's considerably more than Boston's initial $70 million offer. The three-time All-Star could probably get twice that on the open market given his age, durability, and lengthy track record of consistent success. The Red Sox don't have to (and shouldn't) blow him away with Felix Hernandez/Justin Verlander money, but they need to up the ante closer to Matt Cain territory.
Lester's made his intentions known, leaving the ball's in Boston's court. If Cherington doesn't feel his ace is worth a lengthy nine-figure investment, that's well within his right. Lester's going to be 31 next year, his velocity's down and his strikeout rate had declined in the four seasons prior to this one. While still a good pitcher, he's not irreplaceable, especially given the abundance of young pitching talent coming up through the Red Sox pipeline. Letting Lester go would open up an opportunity for a Henry Owings or Anthony Ranaudo. And if the Sox truly are a few years away from contending, then it doesn't make much sense to sign Lester so they can be an 80-win team rather than a 75-win team.
Like with any decision, there are pros and cons and risk that come with signing, or not signing, Jon Lester to a fat contract. The Red Sox have a little more time to weigh their options, but they must make up their minds soon. Because if they don't trade Lester and he leaves in a few months, they're going to be very, very sorry.