Are the Red Sox Insulting Jon Lester with Their Contract Offer? Please

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Am I the only one who doesn’t think the Red Sox’ initial contract offer to Jon Lester was necessarily an “insult?”

Oh, the hue and cry that resulted over the weekend when Fox Sports’ Ken Rosenthal (yet another national guy getting the scoop over the local chapter of the BBWAA, huh?) reported that Boston’s most recent contract offer to the lefty was only for four years and somewhere between $70 and $80 million, an annual average of anywhere from $17.5-$20 million per season. Rosenthal – and plenty of others – see the offer as far below market value, which apparently is simply another way of saying the Red Sox should have to follow the stupid leads of those around you.


Lester (1-2 with a 2.57 ERA this season for the floundering Red Sox) is eligible for free agency at the end of the season, and will certainly land a monstrous deal somewhere should he hit the market. As a comparison for what Lester should expect, the Tigers’ Max Scherzer, the reigning AL Cy Young winner, also in the final year of his deal, recently turned a six-year, $144 million offer, an average of $24 million per season.

Scherzer’s agent is also one Scott Boras, who just so happens to have put one of his clients out of work this season with his contract demands. Wonder if Stephen Drew might give Scherzer a call with some advice? The Tigers could dwarf Clayton Kershaw’s $215 million deal with the Dodgers in an offer, and Boras would still have his guy focused on November.

Rosenthal also uses Homer Bailey’s (49-46, 4.32 ERA lifetime) ridiculous six-year, $105 million contract with the Reds as a sign that the Sox lowballed Lester. Right, because the Sox should be taking their financial cues from the Mensa patients who gave an average pitcher at best a whopping $2.1 million reward for every win on his resume. Bailey, by the way is living up to his name this season, if not exactly his contract, with an 0-1 start, 8.16 ERA, and an NL-leading six home runs allowed over 14 1/3 innings of work. The contract was laughable when it was announced during spring training, and it looks downright Denny Neagle-esque a few, short weeks later.


So, what does it really mean for Lester’s value? And don’t give me the John Lackey comparison. The moment Theo Epstein and the Sox signed Lackey to that five-year, $82.5 million deal in 2009, it was universally lauded as perhaps the worst contract in franchise history. So to use it as a barometer for Lester is like trying to justify why James Patterson got overlooked for a Pulitzer. Frankly, why should Ben Cherington have to make one of his current players happy based on the work of his predecessor? Oh, heavens, the insult of telling Lester he’s worth “only” $17.5-$20 million per season while Lackey was worth $16.5 five years ago. Cherington might have to write a weekly therapist visit into the language of the deal just so Lester can better handle the personal attack.
ESPN sabermetrician Dan Szymborski crunched some numbers and determined that Lester is actually worth $145 million over six seasons, an annual average of $24.2 million. Look, I don’t know the man, but I am extremely confident in the fact that Dan Szymborski is insane.
A $145 million contract would be the 24th-highest in major league history, the sixth-highest awarded to a pitcher. Such an annual number would make Lester the highest-paid pitcher in the American League by this season’s comparison, $1.6 million more than New York’s CC Sabathia.
There’s certainly a level of under appreciation when it comes to debating Lester’s monetary worth, but the fact is that he’s never been a dominating force over his nine years in the league, even despite his four straight 15-win seasons, including a 19-9 campaign. His Baseball Reference similarity score is most comparable to Teddy Higuera, Mark Mulder, and Cole Hamels; Kevin Milwood, Andy Pettitte, and Josh Beckett for pitchers through age 29. Ick.
The one name that stands out in terms of what the Sox can expect out of Lester going forward is Pettitte, the fellow lefty who had a knack for shining in the postseason, something Lester proved he excels at as well, running his career playoff mark to 6-4 with a 2.11 ERA during last year’s World Series run. Pettitte was 19-11 with a 3.81 ERA in his notable postseason career, and a model of consistency over the bulk of his 18-year major league career. Not a bad comparison to have.
Over his career, Pettitte made almost $140 million, an amount if inflated to 2014 dollars would bring it to a total of around $167 million. At age 31, the same age Lester will be next season, Pettitte made $11.5 million, which inflates to $14.7 million 11 years later. This is with the free-spending Yankees, mind you, which either means New York understood what Pettitte’s consistent value was, or the contract landscape in the sport has gotten completely out of control.
Of course, it’s both.
The most logical colleague with which to work a comparison is clearly Adam Wainwright, who signed a five-year, $97.5 million deal with the Cardinals before last season. Both he and Lester are 101-58 lifetime, both average more than 200 innings per season, and both have two World Series rings (though Wainwright earned his second in 2011 on the sidelines after undergoing Tommy John surgery). Wainwright was the same age as Lester will be when he signs a new deal, and went on to have his second-best season in a St. Louis uniform in 2013, going 19-9 with a 2.94 ERA.
He would have absolutely cleaned up in the offseason.
Regrets? Nope.
“I was so happy to go into this offseason and not have to worry about being a free agent,” Wainwright told the St. Louis Post-Dispatch back in January, after Kershaw signed his record-shattering deal with the Dodgers. “I’m right where I want to be. People ask me the same thing about the deal I signed before. Do you have any regrets about signing the deal early? I have no regrets. Once I signed that deal, that was the deal I wanted to sign. I didn’t have to sign it. We worked to get to a number where I felt made it fair for both sides. This is where I wanted to be. Do I think I could have made more money on the free agent market? Absolutely. ナ But you can’t buy happiness. I’m not going to be happier anywhere else than where I am right now.”
Lester is issuing the same message these days, telling media outlets in January he was only looking for a fair deal.
“It’s like Pedey [Dustin Pedroia]. He left a lot of money on the table to stay here. That’s what he wanted to do. I understand that. That’s my choice, that’s his choice.
“I understand that to stay here, you’re not going to get a free-agent deal. You’re not going to do it. You can’t. It’s not possible. You’re bidding against one team. I understand you’re going to take a discount to stay. Do I want to do that? Absolutely.
“But just like they want it to be fair for them, I want it to be fair for me and my family.”
You can debate all you want if you think $70-$80 million is fair or not. But let’s not make it out to be the ultimate insult either.
Five at $100 million, with a maximum of $110 million over the course of the deal seems fair based on Lester’s resume, and doesn’t force the Red Sox from diverting from their “No more Carl Crawfords” mantra. That’s what he’s worth.
Hope that’s not impertinent. One hundred million paydays can confuse me sometimes.

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