I hope your sarcasm detector is ringing off the hook because I am laying it on pretty thick. It is one thing to say you'd be willing to take a "hometown discount," but it's something altogether different to be mocked and ridiculed. What, in the name of Barry Zito, are the Red Sox thinking?
I am the first to criticize the lunacy of professional sports' contracts. $300 million for Miguel Cabrera? You want to pay him $32 million in 2023 when Cabrera is 40 years old? OK. Good luck with that. But this is the world we live in. It doesn't matter if I agree with it or not.
Which brings us back to Jon Lester. Is Lester a top five, or even a top ten, starting pitcher? No. He is not in the same class as Clayton Kershaw or Felix Hernandez. He is not even as good as Adam Wainwright, Yu Darvish, or Stephen Strasburg.
What Lester does bring to the table is his competitiveness. What none of those other guys have is two World Series rings. It's not like Lester was just along for the ride for those championships. Lester has been driving the bus. Lester is 6-4 with a 2.11 ERA in the postseason. Even better, he is 3-0 with a 0.43 ERA in the World Series. 0.43?? That is Koji-esque.
It is one thing to perform during the regular season. It is something else to perform when the spotlight is red hot. The Red Sox know a thing or two about bringing in players who were successful in other markets only to see them fail in Boston. It is not something to be taken lightly. Once the Red Sox have a player that has proven he can succeed here, that is as good as gold. And those players should be paid with gold, not silver.
The other thing Lester has going for him is his durability. Lester has been good for over 30 starts and 190 innings pitched every year since 2008. He has pitched, and flourished, in the American League East-- long believed to be the best offensive division in baseball. If he pitched in the National League, you could chop off about a half run off his 3.74 career ERA.
He is a proven winner. He has a 63.5% winning percentage (101-58) in his career. He is Boston's version of Andy Pettitte. Pettitte had a 62.6% career win percentage, mostly pitching in the AL East with the Yankees, despite a 3.85 career ERA. By comparison, Pettitte was 15-9 with a 4.05 ERA in his age 35 season (in which he made $16 million that year) with New York. Even two years later, Pettitte was 14-8 with a 4.16 ERA. The Red Sox should be more than happy with those numbers.
So what should be acceptable for all sides? Lester is 30 years old. Not bad. He may, in fact, still be getting better. Maybe it's a maturity thing, but Lester looks more and more comfortable with his status as the ace of the Red Sox staff.
Lester has been on the record as saying he'd have a hard time saying no to the six-year, $144 million offer the Tigers presented to Max Scherzer. No kidding. Scherzer shouldn't have said no, either (but he did).
Keeping in mind I hate big contracts, I'd be willing to go five years with Lester. That would bring Lester up to age 35. He has the body build that doesn't scare me. He is not overweight like C.C. Sabathia was when he signed his huge extension. He doesn't have the lanky frame which scared the Red Sox away from signing Pedro Martinez to a lengthy extension late in his career.
We've seen Lester grow up. We've seen him conquer cancer. There is no questioning Lester's toughness and competitiveness. And he wants to play in Boston. This is not a guy who will sign his contract and kick back on the front porch chugging beers. Well, OK, maybe I shouldn't go there.
Now for the money issue. Yeah, that little issue. I think an average of $21 million per season sounds right with most of it front-loaded. That would make my offer five years for $105 million. I'd consider going up to $110 million and possibly throwing in a vesting option for a sixth year.
That would put Lester in the top ten of starting pitcher salaries for 2015. It would put him in the area of Sabathia, Masahiro Tanaka, and Cole Hamels. It would put him just below Felix, Zack Greinke, and Lee. I think that's fair. Will he?