I still feel that way to a degree, because in the end one deal wasn't dependent on the other. The Sox could have re-signed Lester and still brought in Rick Porcello, Wade Miley and Justin Masterson. And having those three guys with Lester at the top of the rotation...I think most Boston fans would feel good about that.
But after Lucchino essentially blew off Lester with that pitiful offer in the spring of 2014, it was going to be an uphill climb getting him back here. And that ended, as we all know, with Lester going to the Cubs for an average of a little over $24M a year over six years with a $25M team option in 2021. The odds of which being exercised are slightly greater than me ever wearing a Yankees hat.
Boston would never have paid him that no matter what, a price that makes him the second highest-paid pitcher in the majors behind Clayton Kershaw. And this is where it gets weird with Lester.
Lester was Boston's ace, but he has never pitched in the regular season like an ace. He has never won 20 games in a season. He has only had a season-long ERA under 2.50 once. He has never led the league in innings pitched, strikeouts or ERA. He has never won a Cy Young, or been a runner-up. And I say this as someone who loves Lester, but it's hard to look at that and then justify paying him $24M into his late 30s. $18-20M I can see, and here's why.
Look at his comparables. The top three similar pitchers to Lester (thanks to the awesome baseball-reference.com) are Jered Weaver, John Tudor and Tim Lincecum.
Lincecum is hard to compare to Lester because of his transcendent first three seasons and then his fall to mediocrity over the last five. Lester has been a much more consistent pitcher. Tudor...different pitcher, different time. Weaver is the interesting one. He has one 20-win season under his belt and led the AL in strikeouts and WHIP once. But that aside, they are very similar in makeup and production. And right now Weaver is making 18M this year and 20M next year at the end of his current deal. And that is where Lester's value lies. Paying out $24M a year...it's a stiff premium.
Similar pitchers through the age of 30? Top three are Tim Hudson, Jack McDowell and Andy Pettitte.
After age 30, Hudson averaged a 12-8 record with a 3.36 ERA (117 ERA+). McDowell barely pitched after hitting 30, starting only 24 games over the last three years of his career. And Pettitte...he pitched another 10 years, averaged a 13-8 record with a 3.77 ERA (116 ERA+).
So going forward, if Lester averages between 12-14 wins with an ERA between 3.30 and 3.75 (his career average is 3.58 right now)...is that worth $24M a year? I think it is hard to argue that it is.
So Lucchino's screw up was in the beginning. I think a fair offer (6, 120M) might have gotten Lester to the table to sign up. But once that window was lost, the Sox were right not to chase the dollars that the Cubs were willing to give Lester. $4M may not seem like a lot in baseball, but that is how you sign key bench players and live arms for your bullpen. That $4M can be the difference between success and failure.
Of course, that leaves the Sox without a top starter. And that brings us to the other deals.
