Ranking the best free agent pitching targets

3. Jon Lester

Aug 23, 2014; Oakland, CA, USA; Oakland Athletics starting pitcher

(31) at the end of the top of the fifth inning against the Los Angeles Angels at O.co Coliseum. Mandatory Credit: Kelley L Cox-USA TODAY Sports

Jon Lester is not at the top of my free agent target list. He is a tremendous player who will almost certainly not be worth the money he makes after year four of the contract he will sign. Despite the wishes of all of Red Sox Nation, I see very little chance of a Lester reunion barring a serious hometown discount, particularly on the length side. If he wants to take a five year deal and come back, then I will embrace him with open arms and shed a tear. I don’t see that happening.

As phenomenal as five year $115 million sounds (I might go all the way up to $130 mil on a five year deal…$26 mil per isn’t totally crippling), Lester likely will take the six or seven years he will almost certainly be offered by New York, Chicago, Texas, or Seattle (or all of the above, OR the always lurking mystery team). Lester’s numbers this year speak for themselves: 16-11, 2.46 ERA, 1.10 WHIP, 220 K’s and a shutout. BUT, we need to take into account more than one year when handing out a mega deal.

As much as I hate to play into the chicken and beer “scandal,” Lester was not exactly an ace in 2012, when he finished with a 4.82 ERA. He didn’t even look like an ace for most of 2013, when he finished with a 3.75 ERA, and people seem to forget just how bad he was most of last year. Buchholz was Boston’s ace last year, even if he missed time, and just like Lester did, he could very easily bounce back next year. Lester would be a great player to have next year. But I don’t believe we can say the same about 2019 and beyond and I think Ben Cherington feels similarly.